|Publication number||US3361673 A|
|Publication date||Jan 2, 1968|
|Filing date||Aug 24, 1959|
|Priority date||Aug 24, 1959|
|Also published as||DE1444798A1, US3202678|
|Publication number||US 3361673 A, US 3361673A, US-A-3361673, US3361673 A, US3361673A|
|Inventors||Robert G Anderson, Alan Y Drummond, Frank A Stuart|
|Original Assignee||Chevron Res|
|Export Citation||BiBTeX, EndNote, RefMan|
|Patent Citations (3), Referenced by (262), Classifications (53)|
|External Links: USPTO, USPTO Assignment, Espacenet|
United States Patent LUBRICATING GIL COMPOSITIONS CONTAENING ALKENYL SUCCINIMIDES 0F TETRAETHYL- ENE PENTAMINE Frank A. Stuart, Oriuda, Robert G. Anderson, Novato, and Alan Y. Drumrnond, Richmond, Calitl, assignors to Chevron Research Company, a corporation of Delaware No Drawing. Filed Aug. 24, 1959, Ser. No. 835,437
6 Claims. (Cl. 252-515) This invention pertains to lubricating oil compositions having incorporated therein metal-free detergents. These particular metal-free detergents are N-substituted polyamine alkenyl succinimides.
Alkenyl succinic anhydrides and numerous derivatives thereof are well known in the art. For example, alkenyl succinic anhydrides in which the alkenyl radical contains from to 20 carbon atoms are taught as corrosion inhibitors in lubricating oil compositions. Also, products obtained by reacting such alkenyl succinic acid anhydrides with monoamines are taught as ferrous corrosion inhibitors for lubricating oil compositions.
However, the above known alkenyl succinimides are not useful as detergents in lubricating oil compositions. In contrast thereto, the N-substituted polyamine alkenyl succinimides which are described herein are new compounds which are useful as detergents in lubricating oil compositions.
Present day internal combustion engines operate at high speeds and high compression ratios. When used in the so-called city stop-and-go driving, which includes the greater part of the driving condition for a large percentage of todays automobiles, the internal combustion engines do not reach the most efficient operating temperature. Under city driving conditions, large amounts of partial oxidation products are formed, and reach the crankcase of the engine by blowing past the piston rings. Most of these partial oxidation products are oil insoluble, tending to form deposits on the various operating parts of the engine, such as the pistons, piston rings, etc. For the purpose of preventing the deposition of these products on the various engine parts, it is necessary to incorporate detergents in the lubricating oil compositions, thus keeping these polymeric products highly dispersed in a condition unfavorable for deposition on metals.
For the most part, the various detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an or ganic group through an oxygen atom. Although these metal-containing organic compounds have some etfectiveness as detergents for dispersing the precursors of deposits within the oil itself rather than permitting Patented Jan. 2, 1968 lubricating oil compositions which are compounded with a metal-free detergent.
Therefore, in accordance with this invention, it has been discovered that lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating N-substituted monoalkenyl succini-rnides derived from tetraethylene pentamine in oils of lubricating viscosity.
By the use of lubricating oil compositions containing the N-substituted alkenyl succinimides described herein, diesel and gasoline engine parts remain remarkably free of deposits and varnish, even under severe operating conditions.
These new compounds, which are monoalkenyl succinimides of tetraethylene pentamine, have the formula:
wherein R is a hydrocarbon radical having a molecular Weight from about 400 to about 3000; that is, R is a hydrocarbon radical containing about 30 to about 200 carbon atoms.
These alkenyl succinimides of tetraethylene pentamine can be prepared by reacting maleic anhydride with an olefinic hydrocarbon, followed by reacting the resulting alkenyl succinic anhydride with tetraethylene pentamine. The R radical of the above formula, that is, the alkenyl radical, is derived from an olefin containing from 2 to 5 carbon atoms. Thus, the alkenyl radical is obtained by polymerizing an olefin containing from 2 to 5 carbon atoms to form a hydrocarbon having a molecular weight ranging from about 400 to about 3000, more preferably, 900 to 1200. Such olefins are exemplified by ethylene, propylene, l-butene, Z-butene, isobutene, and mixtures thereof. Since the methods of polymerizing the olefins to form polymers thereof is immaterial in the formation of the new compound described herein, any of the numerous processes available can be used therefor.
The preparation of N-substituted monoalkenyl succinimides derived from tetraethylene pentamine can be described generally by the following equations, using a polymer of isobutene as an example of the alkenyl radical: I 0
them to form added deposits on the engine parts, I they have the disadvantage of forming ash deposits in the C 3 engine. These ash deposits lower engine performance by CH:C fouling plugs and valves, and contributing to preignition. 11
CH3 CH3 CH3 0 l I CH3CCH2-OH?' CH=CCH2OHC\ GEM-CH2 CHa n /O NH:C2H4N /NH 011 -0 CH2-CH2 CH3 CH3 CH 0 I I GHaCCHz-CHCIJ OH=CCHCHC\ CHPCHQ CH3 /n /NCH2CH2N /NH CHz-O CHa-CH:
It is a particular object of this invention to provide wherein n has a value of about 7 to about 50.
The above reaction between a polyolefin and maleic anhydride is an uncatalyzed addition reaction which should not be confused with a copolymerization reaction such as that obtained with a vinyl monomer and maleic anhydride. While the general reaction of an olefin and maleic anhydride is well known for olefins of low molecular weight (e.g., olefins of 18 carbon atoms), no previous work has been done with maleic anhydride and the high molecular weight olefins as described herein.
The reaction set forth and described by Equation I hereinabove can proceed in a mol ratio of the polyolefin to the maleic anhydride of 1:1 to 1:10, preferably from 1:1 to 1:5. The reaction temperature can vary from 300 F. to 450 F. Because of the greater yield of products obtained thereby, it is preferred to use the high range of temperatures (e.g., 375 F. to 450 F.). In the second step of the reaction as exemplified by Equation II hereinabove, the yield of the imide is extremely high even though the reactants are used in equal molar ratios. This is surprising, since under the conditions of the reaction there is an excess of secondary amino groups over primary amino groups, and any reaction with the secondary amino groups would lead to amide formation; thus, preventing imide formation.
The reaction described by Equation 11 hereinabove can be made at 220 F. to 500 F., preferably from 300 F. to 400 F. The alkenyl succinic anhydride and the tetraethylene pentamine are reacted in about equal molar quantities.
Since the reaction between the polyolefin and maleic anhydride may not go to completion, the resulting alkenyl succinic anhydride may contain some unreacted polyolefin. As it may not be desirable to separate out this unreacted polyolefin at this stage, the resulting imide formed by reaction of the alkenyl succinic anhydride and the diamine will contain this polyolefin as an impurity which can be a diluent in the formation of lubricating oil compositions. However, if it is so desired, this unreacted polyolefin can be removed by precipitation, for example, by acetone or methanol from a hydrocarbon solution.
Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraflin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.-g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene polymers (such as polymers of propylene) butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g., ethyl alcohol, dicarboxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suben'c acid, sebacic acid, salkanol succinic acid, fumaric acid, maleic acid, etc., with alohols such as butyl alcohol, hexyl alcohol, 2-ethyl hexyl alcohol, dodecyl alcohol, etc.), liquid esters of acids of phosphorus, alkyl benzenes (e.g., monoalkyl benzene such as dodecyl benzene, tetradecyl benzene, etc., and dialkyl benzenes (e.g., n-nonyl Z-ethyl hexyl benzene); polyphenyls (e.g., biphenyls and terphenyls), alkyl biphenyl ethers, polymers of silicon (e.g., tetraethyl silicate, tetraisopropyl silicates, tetra(4-methyl-2-tetraethyl) silicate, hexyl (4-methyl-2-pentoxy) disiloxane, poly(methyl) siloxane, poly(methylphenyl) siloxane, etc. Synthetic oils of the alkylene oxide-type polymers which may be used include those exemplified by the alkylene oxide polymers.
The above base oils may be used individually or in combinations thereof, wherever miscible or wherever made so by the use of mutual solvents.
The alkenyl succinimides of tetraalkylene pentamine can be used in oils of lubricating viscosity in amounts of 0.1% to 80%, by weight, preferably 0.25% to 5%, by weight.
The preparation of the alkenyl succinimides of tetraalkylene pent-amine is illustrated in the following examples.
Example I.-Preparati0n 0f polybutenyl succinic anhydride A mixture of 1000 grams (1 mol) of polybutene having a molecular weight of about 1000 and 98 grams (1 mol) of maleic anhydride was heated at 410 F. in a nitrogen atmosphere with agitation for a period of 24 hours. The reaction mixture was cooled to 150 F. and 700 cc. of hexane added; after which the mixture was filtered under vacuum. After vacuum distillation to remove the hexane from the filtrate, the product was maintained at 350 F. at an absolute pressure of 10 mm. Hg for one hour to remove traces of maleic anhydride. The crude polybutenyl succinic anhydride thus prepared had a saponification number of 79.
Example I1.Preparati0n of tetraethylenepentamine derivative 0 the polybutenyl succinic anhydride of Example l hereinabove A mixture of 84 grams (0.45 mol) of tetraethylene pentamine and 702 grams (0.45 mol) of the polybutenyl succinic anhydride of Example I hereinabove, was blended with agitation at 125 F. in a nitrogen atmosphere. The temperature was increased to 400 F. during a period of one hour, after which the absolute pressure was reduced to about 200 mm. Hg during a period of 30 minutes to facilitate the removal of water. The reaction mixture was then allowed to reach room temperature at this reduced pressure. The reaction product contained 5.1% nitrogen (theory=5.4%). Infra-red analysis showed that the reaction product was an imide containing a polybutene side chain.
As detergents for lubricating oil compositions, the compounds of this invention are more efiective than alkenyl succinimides having fewer nitrogen atoms in the amine portion of the molecule, and succinimides having less than 30 carbon atoms in the alkenyl radical. The use of amyl amine, for example, in place of tetraethylene pentamine in the preparation of the succinimide, results in a product which is ineffective as a detergent in lubricating oil compositions.
Table I hereinbelow presents data obtained with lubricating oil compositions containing N-substituted monoalkenyl succinimides derived from tetraethylene pentamine.
The monoalkenyl succinimide used was an N-substituted succinimide derived from tetraethylene pentamine Wherein the alkenyl radical had a molecular weight of about 1000, which alkenyl radical was a polymer of isobutene.
The tests were made in a Caterpillar L-l engine according to Supplement I conditions for a period of 120 hours as described in the Coordinating Research Council Handbook, January, 1946.
The PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 0; to those intermediate between completely black and completely clean are assigned PD numbers intermediate in proportion to the extent and degree of darkening.
The G.D. Nos. refer to the percentage deposits in the piston ring grooves; and 0 evaluation being a clean groove; and a number of 100 being a groove full of deposits.
The base oils were California SAE 30 base oils.
The dithiophosphate was a zinc salt of a mixed dialkyl dithiophosphate wherein one of the alkyl radicals contained 4 carbon atoms and the other alkyl radical contained 5 carbon atoms. The dithiophosphate was present in the lubricating oil compositions in an amount of 18 millimols per kilogram (Le, 18 mm./kg.) of finished product, based on the metal content.
TABLE I A I B o D Additive:
Succiniuu'de, Wt. percent- 0.0 3. 2. 0 Dithiophosphate:
(1) ImJkg 0.0 0.0 18 18 (2) MIn./kg 0.0 0.0 Test Results:
G.D. No 2 39 4 21 1 P.D. N0 2 800, 800, 800 0, 0, O 600, 300, 200 40, 1, 5
1 An alkenyl succinimide of tetraethylene pentamine wherein the allrenyl radical has had a molecular weight of approximately 1,000, which alkenyl radical was a polymer of isooutene 2 These test results were obtained in a Caterpillar L-l test under the MIL-D2104 conditions. Thus, under the more severe supplement-l conditions, these G.D. N as. would be considerably higher.
The marked synergistic efiect obtained by the combina- T ABLE 1H tron of the N-substituted alkenyl succinimides of this invention and the dithiophosphates is particularly noted. I I l I K i L Table II hereinbelow presents data obtained in an FL-2 ti 0 Additive: test, usmg a 6 cylinder Chevrolet engine Opera 11,, fiat succinimide, Wt percent 3'0 3'0 3' 0 3 0 2500 r.p.m for a period of 40 hours, which test is in y Dithiopl1osphate,mm./kg 1s 18 18 18 described in a Coordmatmg Research Council. bulletm Test Results! -t it th Duration of Test (hours) 20 36 52 72 tled Research Technique for the Determination of e gearing Weight 133 133 206 240 Efiects of Fuels and Lubricants on the Formation of De- Plston Varnish Refine posits During Moderate Temperature Operation. (1948).
The piston varnish rating is a visual observation of the amount of varnish on a piston skirt, with 10 being the maximum rating for a perfectly clean piston and a 0 being the rating of a piston fully covered with black varnish. This piston varnish rating correlates with road performance in automobiles.
The total rating is the overall deposit rating of the engine. The rating values range from 0, the poorest value, to 100, the top value. These figures indicate the percentage rating for the engine.
The base oil was an SAE base oil.
The succinimide and the dithiophosphate were the same as those described for Table I hereinabove.
It is readily seen from the data set forth hereinabove in Tables I and II that lubricating oil compositions containing the alkenyl succinimides of tetraethylene pentamine as described herein are superior as lubricating oil compositions for the lubricating of internal combustion engines.
Table 111 hereinbelow presents data obtained with lubricating oil compositions under L-4 test conditions. This L-4 engine test which is fully described in the CRC Handbook, 1946 edition, Coordinating Research Council, New York, New York, is designed to evaluate the bearing corrosion characteristics and high temperature detergency of lubricating oil compositions. The detergency characteristics are rated by the piston varnish rating on the same scale described above for the FL-2 test. The L-4 test was continued beyond the normal 36 hours. The number of hours is the hours at which the same specimens were evaluated then placed in the engine for further testing.
The dithiophosphate was a zinc salt of a dialkyl dithiophosphate wherein one of the alkyl radicals contained 4 carbon atoms and the other alkyl radical contained 5 carbon atoms.
The succinimide and the dithiophosphate were the same as those described hereinabove.
This performance is exceptionally good.
As is known, the use of a number of polymeric ashless detergents and V1. improvers in lubricating oil compositions results in the formation of lead deposits on many of the parts of gasoline engines. These deposits result from the lead halides formed from the tetraethyl lead and the scavengers used in commercial gasolines. Engine failures result from the formation of these deposits. As shown by the data of Table I hereinbelow, the addition of the N-substituted alkenyl succinimides of this invention markedly improves the performance of such oils.
These tests, which correlate with actual road performance, were made in a 6-cylinder Chevrolet engine run at 2500 r.p.m., with 50 brake horsepower, an oil sump temperature of F. for a period of 36 hours, using a commercial gasoline containing 3 cc. of TEL per gallon. The oil was changed after 24 hours.
The lead rating scale ranges from 10 for a clean engine, to zero for an engine containing heavy lead deposits. Similarly, in the same engine test, piston varnish ratings were obtained, a value of 10 for a clean piston, and a value of zero for a piston heavy with varnish.
The succinimide and the dithiophosphate were the same as that described in the tables hereinabove.
TABLE IV Additive: M Succinimide, weight percent 2 Dithiophosphate, mm./kg. 18 Test results:
Lead rating 9.4 Piston varnish rating 9.9 Total rating 99.1
In addition to the dithiophosphate described hereinabove, lubricating oil compositions containing the N-substituted alkenyl succinimides of tetraethylene pentamine of this invention may also contain other detergents, viscosity index improving agents, rust inhibitors, oiliness agents, grease thickening agents, etc.
1. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and in an amount suficient to impart detergency characteristics thereto, a monoalkenyl succinimide of the formula:
7 wherein R is a hydrocarbon radical having a molecular weight of from about 900 to about 3000.
2. A lubricating oil composition consisting essentially of an oil of lubricating viscosity, and from about 0.1% to about 80%, by weight, of a monoalkenyl succinirnide of tetraethylene pentamine of the formula:
RGHi| J lTICH2CHz(NHCH2CH2)s-NH GHzC=-O wherein R is a hydrocarbon radical derived from a polymer of an olefin containing from 2 to carbon atoms, said polymer having a molecular weight in the range of about 900 to about 3000.
3. A lubricating oil composition consisting essentially of an oil of lubricating viscosity, and from about 0.1% to about 80%, by weight, of a monoalkenyl succinirnide of tetraethylene pentamine of the formula:
i RCH(3 NGHzCHz(NHCHzCHg)g-NH1 CH2C=O wherein R is a a hydrocarbon radical derived from a polymer of an olefin containing from 2 to 5 carbon atoms, said polymer having a molecular weight in the range of about 900 to about 1200.
wherein R is a polymer of isobutene having a molecular Weight of about 1000.
5. A lubricating oil composition comprising a major proportion of a petroleum lubricating oil, and from about 0.25% to about 5%, by weight, of an N-substituted monoalkenyl succinimide of the formula:
in which structural formula R is a substantially aliphatic hydrocarbon radical of from to 200 carbon atoms, with an equal molar quantity of tetraethylene pentamine at a temperature in the range of 220 to 360 F.
References Cited UNITED STATES PATENTS 2,490,744 12/ 1949 Trigg et a1 252-392 X 2,604,451 7/ 1952 Rocchini 252-515 2,638,450 5/1953 White et a1. 252-515 DANIEL E. WYMAN, Primary Examiner.
PATRICK P. GARVIN, JULIUS GREENWALD,
G. O. ENOCKSON, Assistant Examiner.
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,361,673 January 2, 1968 Frank A. Stuart et a1.
It is certified that error appears in the above identified patent and that said Letters Patent are hereby corrected as shown below:
Column 1, line 57, "plugs" should read spark plugs Columns 1 and 2, formula II should appear as shown below:
iIH (II-I (fH /O CHgC-CH CH- -C CH=C-CH -CH:C I
CH n /O H NCH CH (NHCH CH -NH CH CH CH O 3 3 3 CH -C-CH CH -IC CH=C-CH CH CH n /NCH CH (NHCH CH -NH CH --C Column 3, line 46, (such as polymers of propylene)" should read (such as polymers of propylene, Column 4, line 6, "of polybutene" should read of a polybutene Column 6, line. 35, "I"-should read IV same column 6, lines 69 to 75, the
formula should appear as shown below:
Signed and sealed this 16th day of December 1969.
Attesting Officer Commissioner of Patents
|Cited Patent||Filing date||Publication date||Applicant||Title|
|US2490744 *||Feb 8, 1947||Dec 6, 1949||Socony Vacuum Oil Co Inc||Antirust agent|
|US2604451 *||Sep 16, 1948||Jul 22, 1952||Gulf Research Development Co||Mineral oil compositions|
|US2638450 *||Jan 17, 1950||May 12, 1953||Socony Vacuum Oil Co Inc||Reaction products of nu-alkylated polyalkylenepolyamines and alkenyl succinic acid anhydrides|
|Citing Patent||Filing date||Publication date||Applicant||Title|
|US3434972 *||Nov 30, 1966||Mar 25, 1969||Chevron Res||Lubricant compositions containing rust inhibitors|
|US4820432 *||Jul 24, 1987||Apr 11, 1989||Exxon Chemical Patents Inc.||Lactone-modified, Mannich base dispersant additives useful in oleaginous compositions|
|US4866139 *||Oct 7, 1986||Sep 12, 1989||Exxon Chemical Patents Inc.||Lactone modified, esterified dispersant additives useful in oleaginous compositions|
|US4866140 *||Oct 7, 1986||Sep 12, 1989||Exxon Chemical Patents Inc.||Lactone modified adducts or reactants and oleaginous compositions containing same|
|US4866141 *||Oct 7, 1986||Sep 12, 1989||Exxon Chemical Patents Inc.||Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same|
|US4870197 *||Dec 12, 1986||Sep 26, 1989||Exxon Chemical Patents Inc.||Method for preparing salts of polyolefinic substituted dicarboxylic acids|
|US4906394 *||Oct 7, 1986||Mar 6, 1990||Exxon Chemical Patents Inc.||Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions|
|US4943382 *||Apr 6, 1988||Jul 24, 1990||Exxon Chemical Patents Inc.||Lactone modified dispersant additives useful in oleaginous compositions|
|US4954276 *||Aug 31, 1989||Sep 4, 1990||Exxon Chemical Patents Inc.||Lactone modified adducts or reactants and oleaginous compositions containing same|
|US4954277 *||Aug 31, 1989||Sep 4, 1990||Exxon Chemical Patents Inc.||Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same|
|US4963275 *||Apr 6, 1988||Oct 16, 1990||Exxon Chemical Patents Inc.||Dispersant additives derived from lactone modified amido-amine adducts|
|US4971711 *||Jan 9, 1989||Nov 20, 1990||Exxon Chemical Patents, Inc.||Lactone-modified, mannich base dispersant additives useful in oleaginous compositions|
|US5032320 *||Feb 28, 1991||Jul 16, 1991||Exxon Chemical Patents Inc.||Lactone modified mono- or dicarboxylic acid based adduct dispersant compositions|
|US5232616 *||Aug 21, 1990||Aug 3, 1993||Chevron Research And Technology Company||Lubricating compositions|
|US5286799 *||Jul 23, 1992||Feb 15, 1994||Chevron Research And Technology Company||Two-step free radical catalyzed process for the preparation of alkenyl succinic anhydride|
|US5292444 *||Oct 2, 1992||Mar 8, 1994||Exxon Research And Engineering Company||Lube oil compositions containing fullerene-grafted polymers|
|US5292813 *||Oct 2, 1992||Mar 8, 1994||Exxon Research & Engineering Co.||Fullerene-grafted polymers and processes of making|
|US5319030 *||Jul 23, 1992||Jun 7, 1994||Chevron Research And Technology Company||One-step process for the preparation of alkenyl succinic anhydride|
|US5356552 *||Oct 12, 1993||Oct 18, 1994||Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc.||Chlorine-free lubricating oils having modified high molecular weight succinimides|
|US5387346 *||Jul 19, 1993||Feb 7, 1995||Ethyl Petroleum Additives, Inc.||Automatic transmission fluids and additives therefor|
|US5430105 *||Nov 22, 1993||Jul 4, 1995||Exxon Chemical Patents Inc.||Low sediment process for forming borated dispersant|
|US5439607 *||Dec 30, 1993||Aug 8, 1995||Exxon Chemical Patents Inc.||Multifunctional viscosity index improver-dispersant antioxidant|
|US5498809 *||May 22, 1995||Mar 12, 1996||Exxon Chemical Patents Inc.||Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives|
|US5554310 *||Jun 9, 1994||Sep 10, 1996||Exxon Chemical Patents Inc.||Trisubstituted unsaturated polymers|
|US5565528 *||Jun 5, 1995||Oct 15, 1996||Chevron Chemical Company||Polymeric dispersants having polyalkylene and succinic groups|
|US5616668 *||Dec 14, 1995||Apr 1, 1997||Chevron Chemical Company||Polymeric dispersants having polyalkylene and succinic groups|
|US5625004 *||Jul 23, 1992||Apr 29, 1997||Chevron Research And Technology Company||Two-step thermal process for the preparation of alkenyl succinic anhydride|
|US5629434 *||Sep 25, 1995||May 13, 1997||Exxon Chemical Patents Inc||Functionalization of polymers based on Koch chemistry and derivatives thereof|
|US5643859 *||Jun 17, 1994||Jul 1, 1997||Exxon Chemical Patents Inc.||Derivatives of polyamines with one primary amine and secondary of tertiary amines|
|US5646332 *||Jun 17, 1994||Jul 8, 1997||Exxon Chemical Patents Inc.||Batch Koch carbonylation process|
|US5650536 *||Jun 17, 1994||Jul 22, 1997||Exxon Chemical Patents Inc.||Continuous process for production of functionalized olefins|
|US5663130 *||Mar 11, 1996||Sep 2, 1997||Exxon Chemical Patents Inc||Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives|
|US5696064 *||Aug 23, 1995||Dec 9, 1997||Exxon Chemical Patents Inc.||Functionalization of polymers based on Koch chemistry and derivatives thereof|
|US5698722 *||Jun 6, 1995||Dec 16, 1997||Exxon Chemical Patents Inc.||Functionalization of polymers based on Koch chemistry and derivatives thereof|
|US5703256 *||Dec 16, 1996||Dec 30, 1997||Exxon Chemical Patents Inc.||Functionalization of polymers based on Koch chemistry and derivatives thereof|
|US5716912 *||Apr 9, 1996||Feb 10, 1998||Chevron Chemical Company||Polyalkylene succinimides and post-treated derivatives thereof|
|US5717039 *||Jun 6, 1995||Feb 10, 1998||Exxon Chemical Patents Inc.||Functionalization of polymers based on Koch chemistry and derivatives thereof|
|US5753597 *||Aug 20, 1996||May 19, 1998||Chevron Chemical Company||Polymeric dispersants|
|US5756428 *||Sep 29, 1988||May 26, 1998||Exxon Chemical Patents Inc.||High functionality low molecular weight oil soluble dispersant additives useful in oleaginous composition|
|US5767046 *||May 15, 1997||Jun 16, 1998||Exxon Chemical Company||Functionalized additives useful in two-cycle engines|
|US5773567 *||Jun 17, 1996||Jun 30, 1998||Exxon Chemical Patents Inc||Carboxylic amide-containing polymers for use as fuel or lubricating oil additives and processes for their preparation|
|US5788722 *||May 30, 1995||Aug 4, 1998||Exxon Chemical Patents Inc||High functionality low molecular weight oil soluble dispersant additives useful in oleaginous compositions|
|US5789356 *||Feb 11, 1997||Aug 4, 1998||Exxon Chemical Patents Inc||Synergistic combinations for use in functional fluid compositions|
|US5792729 *||Aug 20, 1996||Aug 11, 1998||Chevron Chemical Corporation||Dispersant terpolymers|
|US5811377 *||Feb 3, 1997||Sep 22, 1998||Exxon Chemical Patents Inc||Low molecular weight basic nitrogen-containing reaction products as enhanced phosphorus/boron carriers in lubrication oils|
|US5821205 *||Dec 1, 1995||Oct 13, 1998||Chevron Chemical Company||Polyalkylene succinimides and post-treated derivatives thereof|
|US5849676 *||Jul 29, 1997||Dec 15, 1998||Chevron Chemical Company||Post-treated derivatives of polyalkylene succinimides|
|US5851965 *||Jul 29, 1997||Dec 22, 1998||Chevron Chemical Company||Dispersant compositions having polyalkylene succinimides|
|US5853434 *||Jul 29, 1997||Dec 29, 1998||Chevron Chemical Company||Fuel compositions having polyalkylene succinimides and preparation thereof|
|US5861363 *||Jan 29, 1998||Jan 19, 1999||Chevron Chemical Company Llc||Polyalkylene succinimide composition useful in internal combustion engines|
|US5872082 *||Oct 21, 1997||Feb 16, 1999||Exxon Chemical Patents Inc.||Method for increasing the static coefficient of friction in oleaginous compositions|
|US5872083 *||Jul 29, 1997||Feb 16, 1999||Chevron Chemical Company||Post-treated derivatives of polyalkylene succinimides|
|US5880070 *||Aug 20, 1996||Mar 9, 1999||Chevron Chemical Company||Cross-linked succinimides from an acid derivative, a polyamine, and a polycarboxylic acid derivative|
|US6015776 *||Sep 8, 1998||Jan 18, 2000||Chevron Chemical Company||Polyalkylene polysuccinimides and post-treated derivatives thereof|
|US6030930 *||May 14, 1997||Feb 29, 2000||Exxon Chemical Patents Inc||Polymers derived from ethylene and 1-butene for use in the preparation of lubricant disperant additives|
|US6066605 *||Feb 6, 1998||May 23, 2000||Infineum Usa L.P.||Carboxylic amide-containing polymers for use as fuel or lubricating oil additives and processes for their preparation|
|US6107450 *||Dec 15, 1998||Aug 22, 2000||Chevron Chemical Company Llc||Polyalkylene succinimides and post-treated derivatives thereof|
|US6127321 *||Sep 5, 1991||Oct 3, 2000||Exxon Chemical Patents Inc||Oil soluble dispersant additives useful in oleaginous compositions|
|US6140280 *||Oct 8, 1997||Oct 31, 2000||Idemitsu Kosan Co., Ltd.||Succinimide compound and method for producing it, lubricating oil additive comprising the compound and lubricating oil composition comprising the compound for diesel engine|
|US6146431 *||Dec 23, 1999||Nov 14, 2000||Chevron Chemical Company Llc||Polyalkylene polysuccinimides and post-treated derivatives thereof|
|US6214775||Oct 13, 1999||Apr 10, 2001||Chevron Chemical Company Llc||Haze-free post-treated succinimides|
|US6306802||Apr 22, 1997||Oct 23, 2001||Exxon Chemical Patents Inc.||Mixed antioxidant composition|
|US6355074||May 25, 1995||Mar 12, 2002||Exxon Chemical Patents Inc||Oil soluble dispersant additives useful in oleaginous compositions|
|US6358892 *||Jan 27, 1998||Mar 19, 2002||Chevron Chemical Company||Polyalkylene succinimides and post-treated derivatives thereof|
|US6440905||Apr 24, 2001||Aug 27, 2002||The Lubrizol Corporation||Surfactants and dispersants by in-line reaction|
|US6642191||Nov 29, 2001||Nov 4, 2003||Chevron Oronite Company Llc||Lubricating oil additive system particularly useful for natural gas fueled engines|
|US6756348||Nov 29, 2001||Jun 29, 2004||Chevron Oronite Company Llc||Lubricating oil having enhanced resistance to oxidation, nitration and viscosity increase|
|US6827750||Aug 24, 2001||Dec 7, 2004||Dober Chemical Corp||Controlled release additives in fuel systems|
|US6835218||Aug 24, 2001||Dec 28, 2004||Dober Chemical Corp.||Fuel additive compositions|
|US6860241||Aug 24, 2001||Mar 1, 2005||Dober Chemical Corp.||Fuel filter including slow release additive|
|US6867171||Nov 27, 2002||Mar 15, 2005||Chevron Oronitz Company Llc||Low molecular weight branched alkenyl succinic acid derivatives prepared from low molecular weight polyisobutene and unsaturated acidic reagents|
|US6906011||Nov 9, 2001||Jun 14, 2005||Chevron Oronite Company Llc||Polymeric dispersants prepared from copolymers of low molecular weight polyisobutene and unsaturated acidic reagent|
|US7001531||Aug 24, 2001||Feb 21, 2006||Dober Chemical Corp.||Sustained release coolant additive composition|
|US7182795||Mar 13, 2002||Feb 27, 2007||Atton Chemical Intangibles Llc||Fuel lubricity additives derived from hydrocarbyl succinic anhydrides and hydroxy amines, and middle distillate fuels containing same|
|US7361629||Mar 10, 2004||Apr 22, 2008||Afton Chemical Corporation||Additives for lubricants and fuels|
|US7422161||Mar 30, 2006||Sep 9, 2008||Afton Chemical Corporation||Treated port fuel injectors|
|US7485734||Jan 28, 2005||Feb 3, 2009||Afton Chemical Corporation||Seal swell agent and process therefor|
|US7563314||Nov 30, 2005||Jul 21, 2009||Xerox Corporation||Ink carriers containing nanoparticles, phase change inks including same and methods for making same|
|US7581558||Jun 5, 2007||Sep 1, 2009||Cummins Filtration Ip Inc.||Controlled release of additives in fluid systems|
|US7591279||Aug 16, 2002||Sep 22, 2009||Cummins Filtration Ip Inc.||Controlled release of additives in fluid systems|
|US7618928||Nov 17, 2009||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7645728||Jan 12, 2010||Afton Chemical Corporation||Lubricant and fuel additives derived from treated amines|
|US7655084||Feb 2, 2010||Xerox Corporation||Carbon black inks and method for making same|
|US7662887||Feb 16, 2010||Infineum International Limited||Method of forming polyalkene substituted carboxylic acid compositions|
|US7682491||Mar 26, 2007||Mar 23, 2010||Nalco Company||Antifoulant for hydrocarbon processing equipment|
|US7700673||Dec 22, 2006||Apr 20, 2010||Bridgestone Corporation||Reduced oil rubber compositions including N-substituted polyalkylene succinimide derivates and methods for preparing such compositions|
|US7745542||Jun 29, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7786209||Aug 31, 2010||Xerox Corporation||Nanostructured particles, phase change inks including same and methods for making same|
|US7816309||Oct 19, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7820602||Jul 12, 2006||Oct 26, 2010||King Industries, Inc.||Amine tungstates and lubricant compositions|
|US7820604||Oct 26, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7820605||Oct 26, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7858566||Oct 27, 2006||Dec 28, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7863228||Mar 17, 2008||Jan 4, 2011||Afton Chemical Corporation||Additives for lubricants and fuels|
|US7875576||Jul 29, 2004||Jan 25, 2011||Chevron Oronite Company Llc||Lubricating oil composition for internal combustion engines|
|US7883638||May 27, 2008||Feb 8, 2011||Dober Chemical Corporation||Controlled release cooling additive compositions|
|US7884058||Feb 8, 2011||Chevron Oronite Company Llc||Stable colloidal suspensions and lubricating oil compositions containing same|
|US7928044||Oct 27, 2006||Apr 19, 2011||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7938277||May 10, 2011||Dober Chemical Corporation||Controlled release of microbiocides|
|US7947636||Feb 27, 2004||May 24, 2011||Afton Chemical Corporation||Power transmission fluids|
|US8029861||Sep 23, 2008||Oct 4, 2011||Xerox Corporation||Ink carriers containing low viscosity functionalized waxes, phase change inks including same, and methods for making same|
|US8067347||Oct 27, 2006||Nov 29, 2011||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US8080500||Dec 20, 2011||King Industries, Inc.||Amine tungstates and lubricant compositions|
|US8109287||Feb 7, 2012||Cummins Filtration Ip, Inc.||Controlled release of additives in fluid systems|
|US8123344||Aug 4, 2008||Feb 28, 2012||Xerox Corporation||Ink carriers containing surface modified nanoparticles, phase change inks including same, and methods for making same|
|US8153566||Sep 30, 2008||Apr 10, 2012||Cherron Oronite Company LLC||Lubricating oil compositions|
|US8177897||Nov 17, 2008||May 15, 2012||Xerox Corporation||Phase change inks containing graphene-based carbon allotrope colorants|
|US8348409||Nov 17, 2008||Jan 8, 2013||Xerox Corporation||Ink jet inks containing nanodiamond black colorants|
|US8389609||Jun 30, 2010||Mar 5, 2013||Bridgestone Corporation||Multiple-acid-derived metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions|
|US8425772||Apr 23, 2013||Cummins Filtration Ip, Inc.||Filtration device with releasable additive|
|US8455568||Jun 4, 2013||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US8546464||Jun 26, 2009||Oct 1, 2013||Bridgestone Corporation||Rubber compositions including metal-functionalized polyisobutylene derivatives and methods for preparing such compositions|
|US8591747||May 26, 2009||Nov 26, 2013||Dober Chemical Corp.||Devices and methods for controlled release of additive compositions|
|US8690968||Apr 4, 2008||Apr 8, 2014||Afton Chemical Corporation||Succinimide lubricity additive for diesel fuel and a method for reducing wear scarring in an engine|
|US8702995||May 27, 2008||Apr 22, 2014||Dober Chemical Corp.||Controlled release of microbiocides|
|US8802755||Mar 11, 2013||Aug 12, 2014||Bridgestone Corporation||Rubber compositions including metal phosphate esters|
|US8901050||Mar 31, 2010||Dec 2, 2014||Chevron Oronite Company Llc||Method for improving copper corrosion performance|
|US8933001||Mar 31, 2010||Jan 13, 2015||Chevron Oronite Company Llc||Method for improving fluorocarbon elastomer seal compatibility|
|US9011556||Mar 9, 2007||Apr 21, 2015||Afton Chemical Corporation||Fuel composition containing a hydrocarbyl-substituted succinimide|
|US9062265||Feb 4, 2011||Jun 23, 2015||Innospec Limited||Diesel fuel compositions for high pressure fuel systems|
|US9090127||Dec 31, 2008||Jul 28, 2015||Bridgestone Corporation||Metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions|
|US9315753||Aug 2, 2012||Apr 19, 2016||Innospec Limited||Diesel fuel compositions|
|US20030122104 *||Feb 12, 2003||Jul 3, 2003||Dober Chemical Corporation||Liquid replacement systems|
|US20030130140 *||Nov 9, 2001||Jul 10, 2003||Harrison James J.||Polymeric dispersants prepared from copolymers of low molecular weight polyisobutene and unsaturated acidic reagent|
|US20030172584 *||Mar 13, 2002||Sep 18, 2003||Henly Timothy J.||Fuel lubricity additives derived from hydrocarbyl succinic anhydrides and hydroxy amines, and middle distillate fuels containing same|
|US20030224948 *||Feb 14, 2003||Dec 4, 2003||Dam Willem Van||Lubricating oil additive comprising EC-treated succinimide, borated dispersant and corrosion inhibitor|
|US20040048765 *||Sep 10, 2001||Mar 11, 2004||Cooney Anthony Michael||Composition|
|US20040091654 *||Nov 3, 2003||May 13, 2004||Fleetguard, Inc.||Controlled release of additives in cooling systems|
|US20040102338 *||Nov 27, 2002||May 27, 2004||Harrison James J.||Low molecular weight branched alkenyl succinic acid derivatives prepared from low molecular weight polyisobutene and unsaturated acidic reagents|
|US20040235682 *||May 22, 2003||Nov 25, 2004||Chevron Oronite Company Llc||Low emission diesel lubricant with improved corrosion protection|
|US20050019236 *||Aug 16, 2002||Jan 27, 2005||Harold Martin||Controlled release of additives in fluid systems|
|US20050027592 *||Jul 30, 2003||Feb 3, 2005||Pettigrew F. Alexander||Powered platform fuel consumption economy credits method|
|US20050070445 *||Sep 30, 2003||Mar 31, 2005||Nelson Kenneth D.||Stable colloidal suspensions and lubricating oil compositions containing same|
|US20050101496 *||Nov 6, 2003||May 12, 2005||Loper John T.||Hydrocarbyl dispersants and compositions containing the dispersants|
|US20050119134 *||Dec 16, 2003||Jun 2, 2005||Chevron Oronite S.A.||Additive composition for transmission oil|
|US20050181959 *||Feb 17, 2004||Aug 18, 2005||Esche Carl K.Jr.||Lubricant and fuel additives derived from treated amines|
|US20050192185 *||Feb 27, 2004||Sep 1, 2005||Saathoff Lee D.||Power transmission fluids|
|US20050202980 *||Mar 10, 2004||Sep 15, 2005||Loper John T.||Novel additives for lubricants and fuels|
|US20050223630 *||Feb 13, 2003||Oct 13, 2005||Cooney Anthony M||Friction modifier for hydrocarbon fuels|
|US20050250656 *||May 4, 2004||Nov 10, 2005||Masahiro Ishikawa||Continuously variable transmission fluid|
|US20060025313 *||Jul 29, 2004||Feb 2, 2006||Chevron Oronite Company Llc||Lubricating oil composition for internal combustion engines|
|US20060122073 *||Dec 8, 2004||Jun 8, 2006||Chip Hewette||Oxidation stable gear oil compositions|
|US20060173217 *||Jan 28, 2005||Aug 3, 2006||Abbas Kadkhodayan||Seal swell agent and process therefor|
|US20070000831 *||Sep 5, 2006||Jan 4, 2007||Fleetguard, Inc.||Controlled release of additives in cooling systems|
|US20070027267 *||Jul 27, 2006||Feb 1, 2007||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20070042917 *||Jul 12, 2006||Feb 22, 2007||Ramanathan Ravichandran||Amine Tungstates and Lubricant Compositions|
|US20070049503 *||Aug 31, 2005||Mar 1, 2007||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20070119340 *||Nov 30, 2005||May 31, 2007||Xerox Corporation||Ink carriers containing nanoparticles, phase change inks including same and methods for making same|
|US20070131138 *||Dec 12, 2005||Jun 14, 2007||Xerox Corporation||Carbon black inks and method for making same|
|US20070149689 *||Dec 28, 2006||Jun 28, 2007||Xiaorong Wang||Rubber composition having good wet-traction properties and a low aromatic-oil content|
|US20070235566 *||Mar 30, 2006||Oct 11, 2007||Hou Peter W||Treated port fuel injectors|
|US20070241042 *||Jun 5, 2007||Oct 18, 2007||Dober Chemical Corporation||Controlled release of additives in fluid systems|
|US20070245621 *||Apr 20, 2006||Oct 25, 2007||Malfer Dennis J||Additives for minimizing injector fouling and valve deposits and their uses|
|US20070283618 *||Jun 9, 2006||Dec 13, 2007||Malfer Dennis J||Diesel detergents|
|US20080098930 *||Nov 1, 2006||May 1, 2008||Xerox Corporation||Colorant dispersant|
|US20080103074 *||Oct 27, 2006||May 1, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080103075 *||Oct 27, 2006||May 1, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080103076 *||Oct 27, 2006||May 1, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080103236 *||Oct 27, 2006||May 1, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080103250 *||Sep 21, 2007||May 1, 2008||Xerox Corporation||Nanostructed particles, phase change inks including same and methods for making same|
|US20080113888 *||Oct 27, 2006||May 15, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080113889 *||Oct 27, 2006||May 15, 2008||Chevron Oronite Company Llc||lubricating oil additive composition and method of making the same|
|US20080153724 *||Dec 4, 2007||Jun 26, 2008||Pierre Tequi||Additive composition for transmission oil containing hydrated alkali metal borate and hexagonal boron nitride|
|US20080194440 *||Apr 3, 2008||Aug 14, 2008||Ramanathan Ravichandran||Amine tungstates and lubricant compositions|
|US20080241095 *||Mar 26, 2007||Oct 2, 2008||Syrinek Allen R||Antifoulant for hydrocarbon processing equipment|
|US20080280793 *||Jul 9, 2008||Nov 13, 2008||Chevron Oronite S.A.||Additive composition for transmission oil containing hexagonal boron nitride and polymethacrylate or dispersant olefin co-polymer|
|US20080296234 *||May 27, 2008||Dec 4, 2008||Dober Chemical Corporation||Controlled release of microbiocides|
|US20090029888 *||Jan 18, 2008||Jan 29, 2009||Ramanathan Ravichandran||Amine tungstates and lubricant compositions|
|US20090031614 *||Aug 1, 2007||Feb 5, 2009||Ian Macpherson||Environmentally-Friendly Fuel Compositions|
|US20090042752 *||Aug 9, 2007||Feb 12, 2009||Malcolm Waddoups||Lubricant Compositions with Reduced Phosphorous Content for Engines having Catalytic Converters|
|US20090156445 *||Dec 13, 2007||Jun 18, 2009||Lam William Y||Lubricant composition suitable for engines fueled by alternate fuels|
|US20090171031 *||Dec 26, 2007||Jul 2, 2009||Richard Joseph Severt||Method of Forming Polyalkene Substituted Carboxylic Acid Compositions|
|US20090249683 *||Apr 4, 2008||Oct 8, 2009||Schwab Scott D||Succinimide lubricity additive for diesel fuel and a method for reducing wear scarring in an engine|
|US20090270531 *||Oct 29, 2009||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20090283466 *||Nov 19, 2009||Cummins Filtration Ip Inc.||Controlled release of additives in fluid systems|
|US20090294345 *||Dec 3, 2009||Dober Chemical Corporation||Controlled release of microbiocides|
|US20090304868 *||Dec 10, 2009||Dober Chemical Corporation||Controlled release cooling additive composition|
|US20100028537 *||Feb 4, 2010||Xerox Corporation||Ink Carriers Containing Surface Modified Nanoparticles, Phase Change Inks Including Same, and Methods for Making Same|
|US20100075038 *||Mar 25, 2010||Xerox Corporation||Ink Carriers Containing Low Viscosity Functionalized Waxes, Phase Change Inks Including Same, And Methods For Making Same|
|US20100081588 *||Apr 1, 2010||Chevron Oronite Company Llc||Lubricating oil compositions|
|US20100107478 *||Apr 15, 2008||May 6, 2010||Instituto Mexicano Del Petroleo||Oxazolidines derived from polyalkyl or polyalkenyl n-hydroxyalkyl succinimides, obtainment process and use|
|US20100123746 *||Nov 17, 2008||May 20, 2010||Xerox Corporation||Ink jet inks containing nanodiamond black colorants|
|US20100124611 *||Nov 17, 2008||May 20, 2010||Xerox Corporation||Phase Change Inks Containing Graphene-Based Carbon Allotrope Colorants|
|US20100160192 *||Dec 22, 2008||Jun 24, 2010||Chevron Oronite LLC||lubricating oil additive composition and method of making the same|
|US20110010985 *||Sep 21, 2010||Jan 20, 2011||Peter Wangqi Hou||Fuel Additive to Control Deposit Formation|
|US20110039994 *||Jun 30, 2010||Feb 17, 2011||Xiaorong Wang||Multiple-Acid-Derived Metal Soaps Incorporated In Rubber Compositions And Method For Incorporating Such Soaps In Rubber Compositions|
|US20110060062 *||Mar 10, 2011||Bridgestone Corporation||Compositions and method for making hollow nanoparticles from metal soaps|
|US20110098378 *||Jun 26, 2009||Apr 28, 2011||Xiaorong Wang||Rubber compositions including metal-functionalized polyisobutylene derivatives and methods for preparing such compositions|
|CN1043772C *||Dec 15, 1992||Jun 23, 1999||中国石油化工总公司石油化工科学研究院||Method for preparation of dispersed oil additives|
|EP0351964A1||Jun 23, 1989||Jan 24, 1990||Exxon Chemical Patents Inc.||Synergistic combination of additives useful in power transmitting compositions|
|EP0399764A1||May 21, 1990||Nov 28, 1990||Ethyl Petroleum Additives Limited||Lubricant compositions|
|EP0515027A2 *||Apr 10, 1992||Nov 25, 1992||Exxon Chemical Patents Inc.||Process for preventing fouling in the production of ethylene dichloride|
|EP0611818A1||Jul 30, 1991||Aug 24, 1994||Exxon Chemical Patents Inc.||Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing the same|
|EP0683220A2||May 18, 1995||Nov 22, 1995||Ethyl Corporation||Lubricant additive compositions|
|EP0776963A1||Nov 29, 1996||Jun 4, 1997||Chevron Chemical Company||Polyalkylene succinimides and post-treated derivatives thereof|
|EP0831104A2||Dec 5, 1996||Mar 25, 1998||Chevron Chemical Company||Novel dispersant terpolymers|
|EP1503316A1||Jul 28, 2004||Feb 2, 2005||Ethyl Petroleum Additives, Inc.||Fuel consumption economy credits method|
|EP1640440A1||Aug 30, 2005||Mar 29, 2006||Infineum International Limited||Friction and/or wear reduction in manual or automated manual transmissions|
|EP1669436A1||Dec 8, 2005||Jun 14, 2006||Afton Chemical Corporation||Oxidation stable gear oil compositions|
|EP1757673A1||Aug 23, 2005||Feb 28, 2007||Chevron Oronite Company LLC||Lubricating oil composition for internal combustion engines|
|EP1840192A1||Jan 9, 2007||Oct 3, 2007||Afton Chemical Corporation||Treated port fuel injectors|
|EP1916292A1||Oct 26, 2007||Apr 30, 2008||Chevron Oronite Company LLC||A lubricating oil additive composition and method of making the same|
|EP1916293A1||Oct 26, 2007||Apr 30, 2008||Chevron Oronite Company LLC||A lubricating oil additive composition and method of making the same|
|EP1970430A2||Jan 24, 2008||Sep 17, 2008||Afton Chemical Corporation||Fuel composition containing a hydrocarbyl-substituted succinimide|
|EP2025737A1||Jul 30, 2008||Feb 18, 2009||Afton Chemical Corporation||Environmentally-friendly fuel compositions|
|EP2031045A1||Jul 29, 2008||Mar 4, 2009||Infineum International Limited||Lubricant compositions with reduced phosphorous content for engines having catalytic converters|
|EP2042582A2||Aug 25, 2008||Apr 1, 2009||Afton Chemical Corporation||Surface passivation and to methods for the reduction of fuel thermal degradation deposits|
|EP2072611A1||Nov 11, 2008||Jun 24, 2009||Afton Chemical Corporation||Lubricant composition suitable for engines fueled by alternate fuels|
|EP2075264A1||Dec 4, 2008||Jul 1, 2009||Infineum International Limited||Method of forming polyalkene substituted carboxylic acid compositions|
|EP2107102A2||Apr 3, 2009||Oct 7, 2009||Afton Chemical Corporation||A succinimide lubricity additive for diesel fuel|
|EP2184338A2||Dec 7, 2004||May 12, 2010||The Lubrizol Corporation||Lubricating composition containing metal salixarate as detergent and succinimides as dispersants|
|EP2272940A1||Sep 13, 2002||Jan 12, 2011||Afton Chemical Intangibles LLC||Fuels compositions for direct injection gasoline engines|
|EP2290040A1||Jul 29, 2010||Mar 2, 2011||Chevron Japan Ltd.||Friction modifier and transmission oil|
|EP2431448A1||Feb 24, 2010||Mar 21, 2012||The Lubrizol Corporation||Lubricating compositions containing the reaction product of an aromatic amine and a carboxylic functionalised polymer and dispersant|
|EP2554636A1||Aug 3, 2011||Feb 6, 2013||Innospec Limited||Fuel compositions|
|EP2644684A1||Feb 25, 2010||Oct 2, 2013||Innospec Limited||Methods and uses relating to fuel compositions|
|EP2851413A1||Sep 17, 2014||Mar 25, 2015||Chevron Japan Ltd.||Fuel economy engine oil composition|
|EP2966151A1||Mar 10, 2011||Jan 13, 2016||Innospec Limited||Fuel composition comprising detergent and quaternary ammonium salt additive|
|EP2998384A1||Jun 13, 2006||Mar 23, 2016||The Lubrizol Corporation||Diesel fuel composition comprising a quaternary ammonium salt detergent|
|WO1998047989A1||Mar 19, 1998||Oct 29, 1998||Exxon Chemical Patents Inc.||Power transmission fluids containing alkyl phosphonates|
|WO2008130214A1 *||Apr 15, 2008||Oct 30, 2008||Instituto Mexicano Del Petróleo||Oxazolidines derived from polyalkyl or polyalkylene n-hydroxyalkyl succinimides, method for preparation and use|
|WO2010099136A1||Feb 24, 2010||Sep 2, 2010||The Lubrizol Corporation||Lubricating compositions containing the reaction product of an aromatic amine and a carboxylic functionalised polymer and dispersant|
|WO2010147993A1||Jun 15, 2010||Dec 23, 2010||Chevron Phillips Chemical Company Lp||Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends|
|WO2010148652A1||Jun 25, 2010||Dec 29, 2010||China Petroleum & Chemical Corporation||Diesel composition and process for improving oxidation stability of biodiesel|
|WO2011059626A1||Oct 14, 2010||May 19, 2011||The Lubrizol Corporation||Lubricant system clean-up compositions and methods thereof|
|WO2011095819A1||Feb 4, 2011||Aug 11, 2011||Innospec Limited||Fuel compositions|
|WO2011102835A1||Feb 19, 2010||Aug 25, 2011||Toyota Jidosha Kabushiki Kaisha||Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents|
|WO2011102836A1||Feb 19, 2010||Aug 25, 2011||Infineum International Limited||Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents|
|WO2011110860A1||Mar 10, 2011||Sep 15, 2011||Innospec Limited||Fuel composition comprising detergent and quaternary ammonium salt additive|
|WO2011141731A1||May 10, 2011||Nov 17, 2011||Innospec Limited||Composition, method and use|
|WO2011146289A1||May 11, 2011||Nov 24, 2011||The Lubrizol Corporation||Methods and compositions that provide detergency|
|WO2011146456A1||May 17, 2011||Nov 24, 2011||The Lubrizol Corporation||Low ash lubricants with improved seal and corrosion performance|
|WO2011149799A1||May 23, 2011||Dec 1, 2011||The Lubrizol Corporation||Method to provide power gain in an engine|
|WO2011153178A2||Jun 1, 2011||Dec 8, 2011||The Lubrizol Corporation||Lubricating composition containing a carboxylic functionalised polymer|
|WO2011159742A1||Jun 15, 2011||Dec 22, 2011||The Lubrizol Corporation||Methods of removing deposits in oil and gas applications|
|WO2012027254A1||Aug 22, 2011||Mar 1, 2012||The Lubrizol Corporation||Lubricants containing aromatic dispersants and titanium|
|WO2012084906A1||Dec 20, 2011||Jun 28, 2012||Rhodia Operations||Fuel additive composition containing a dispersion of iron particles and a detergent|
|WO2012162020A1||May 15, 2012||Nov 29, 2012||The Lubrizol Corporation||Stabilized blends containing antioxidants|
|WO2012162027A1||May 15, 2012||Nov 29, 2012||The Lubrizol Corporation||Stabilized blends containing friction modifiers|
|WO2012162219A1||May 21, 2012||Nov 29, 2012||The Lubrizol Corporation||Stabilized blends containing friction modifiers|
|WO2012162282A1||May 22, 2012||Nov 29, 2012||The Lubrizol Corporation||Stabilized blends containing friction modifiers|
|WO2012177529A1||Jun 18, 2012||Dec 27, 2012||The Lubrizol Corporation||Lubricating compositions containing salts of hydrocarbyl substituted acylating agents|
|WO2013017884A1||Aug 2, 2012||Feb 7, 2013||Innospec Limited||Fuel compositions|
|WO2013017886A1||Aug 2, 2012||Feb 7, 2013||Innospec Limited||Fuel compositions|
|WO2013017887A1||Aug 2, 2012||Feb 7, 2013||Innospec Limited||Fuel compositions|
|WO2013017889A1||Aug 2, 2012||Feb 7, 2013||Innospec Limited||Fuel compositions|
|WO2013043332A1||Aug 29, 2012||Mar 28, 2013||The Lubrizol Corporation||Quaternary ammonium salts in heating oils|
|WO2013062924A2||Oct 23, 2012||May 2, 2013||The Lubrizol Corporation||Lubricating composition containing an esterified polymer|
|WO2013123102A2||Feb 14, 2013||Aug 22, 2013||The Lubrizol Corporation||Lubricating composition including esterified copolymer and low dispersant levels suitable for driveline applications|
|WO2013123160A1||Feb 14, 2013||Aug 22, 2013||The Lubrizol Corporation||Mixtures of olefin-ester copolymer with polyolefin as viscosity modifier|
|WO2014047017A1||Sep 17, 2013||Mar 27, 2014||The Lubrizol Corporation||Lubricant comprising a mixture of an olefin-ester copolymer with an ethylene alpha-olefin copolymer|
|WO2014066344A1||Oct 22, 2013||May 1, 2014||The Lubrizol Corporation||Diesel detergent without a low molecular weight penalty|
|WO2014137800A1||Feb 28, 2014||Sep 12, 2014||The Lubrizol Corporation||Ion tolerant corrosion inhibitors and inhibitor combinations for fuels|
|WO2014193692A1||May 20, 2014||Dec 4, 2014||The Lubrizol Corporation||Asphaltene inhibition|
|WO2015183908A1||May 27, 2015||Dec 3, 2015||The Lubrizol Corporation||Low molecular weight imide containing quaternary ammonium salts|
|WO2015183916A1||May 27, 2015||Dec 3, 2015||The Lubrizol Corporation||Low molecular weight amide/ester containing quaternary ammonium salts|
|WO2015184247A1||May 29, 2015||Dec 3, 2015||The Lubrizol Corporation||High molecular weight imide containing quaternary ammonium salts|
|WO2015184251A1||May 29, 2015||Dec 3, 2015||The Lubrizol Corporation||Branched amine containing quaternary ammonium salts|
|WO2015184254A1||May 29, 2015||Dec 3, 2015||The Lubrizol Corporation||High molecular weight amide/ester containing quaternary ammonium salts|
|WO2015184276A1||May 29, 2015||Dec 3, 2015||The Lubrizol Corporation||Epoxide quaternized quaternary ammonium salts|
|WO2015184280A1||May 29, 2015||Dec 3, 2015||The Lubrizol Corporation||Imidazole containing quaternary ammonium salts|
|WO2015184301A2||May 29, 2015||Dec 3, 2015||The Lubrizol Corporation||Coupled quaternary ammonium salts|
|Cooperative Classification||C10M2229/043, C10M2205/024, C10M2229/042, C10M2229/046, C10M2205/026, C10M2203/104, C10M2203/04, C10M2229/048, C10M2229/041, C10M2207/34, C10M2203/10, C10M2227/04, C10M2203/024, C10M2223/045, C10N2250/10, C10M2217/046, C10M2203/02, C10N2210/02, C10N2240/101, C10M2203/106, C10M2229/044, C10M2215/086, C10M2207/04, C10M2215/04, C10M2209/109, C10M2205/00, C10M2215/26, C10M2203/102, C10M2223/04, C10M133/56, C10M2217/06, C10M2215/28, C10M2209/108, C10M2203/108, C10M2227/02, C10M2203/022, C10M2229/047, C10N2240/10, C08F8/46, C10N2240/106, C10N2240/104, C10M2209/105, C10M2207/282, C10M2223/042, C10M2229/045, C10M2203/06, C10M2229/04, C08F8/32|
|European Classification||C08F8/32, C08F8/46, C10M133/56|