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Publication numberUS3438757 A
Publication typeGrant
Publication dateApr 15, 1969
Filing dateJun 21, 1967
Priority dateAug 23, 1965
Also published asDE1289355B, DE1289355C2, DE1545487A1, DE1545487B2, DE1545487C3, US3565804, US3574576
Publication numberUS 3438757 A, US 3438757A, US-A-3438757, US3438757 A, US3438757A
InventorsRobert Gordon Anderson, Lewis R Honnen
Original AssigneeChevron Res
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Hydrocarbyl amines for fuel detergents
US 3438757 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

United States Patent O 3,438,757 HYDROCARBYL AMINES FOR FUEL DETERGENTS Lewis R. Honnen and Robert Gordon Anderson, Novato, Califi, assignors to Chevron Research Company, San Francisco, Calif., a corporation of Delaware N Drawing. Continuation-impart of applications Ser. No. 408,686, Nov. 3, 1964, Ser. No. 481,916, Aug. 23, 1965, Ser. No. 488,775, Sept. 20, 1965, and Ser. No. 538,571, Mar. 30, 1966. This application June 21, 1967, Ser. No.

Int. Cl. C101 1/22 U.S. C]. 44-58 12 Claims ABSTRACT OF THE DISCLOSURE Hydrocarbyl amines and polyamines substantially free of aromatic unsaturation of from about 450 to 10,000 molecular weight find use as detergents in fuels, particularly in combination with a small amount of an oil. The amine portion is primarily amino or alkylene polyamine.

CROSS-REFERENCES TO RELATED APPLICATIONS This application is a continuation-impart of application Ser. Nos. 538,571, filed Mar. 30, 1966, now abandoned; 488,775, filed Sept. 20, 1965; 481,916, filed Aug. 23, 1965, now abandoned; and 408,686, filed Nov. 3, 1964.

BACKGROUND OF THE INVENTION Field of the invention Deposits resulting from polymeric materials in fuels remain a continuing problem in the smooth operation of internal combustion engines. The narrow tolerances and constricted openings, particularly in the carburetor, ports and valves of the engine, permit of numerous opportunities for deposits to seriously reduce operating etficiency. Therefore, detergents are included in fuels not only to maintain the carburetor clean, but extended detergent action is also disirable. That is, the detergent should also operate to clean the ports and valves through which the fuel-air mixture moves, so as to permit unrestricted flow into the piston chambers. It is extremely difficult to obtain a satisfactory detergent which is effective in the various areas and under the different conditions at which deposits occur in the engine. The problems are made more severe by the low concentrations which must be used in the fuel.

Description of the prior art Numerous patents have issued disclosing relatively low molecular weight amine derivatives as fuel detergents. See, for example, U.S. Patents 3,231,348 and 3,050,043. Higher molecular weigh-t succinimide derivative are reported as fuel detergents in 3,219,666.

SUMMARY OF THE INVENTION used in the fuel have molecular Weights in the range of about 425 to 10,000 more usually in the range of about 450 to 5,000.

3,438,757 Patented Apr. 15, 1969 DESCRIPTION OF THE PREFERRED EMBODIMENTS The compositions which find use in this invention will for the most part have the following formula:

The above symbols are defined as follows:

A-hydrogen, hydrocarbyl of from 1 to 10 carbon atoms, and hydroxyhydrocarbyl of from 1 to 10 carbon atoms Xhydrogen, hydrocarbyl of from 1 to 10 carbon atoms, hydroxyhydrocarbyl of from 1 to 10 carbon atoms, and may be taken together with A to form a ring of from 5 to 6 annular members and up to 12 carbon atoms U-alkylene of from 2 to 6 carbon atoms, there being at least 2 carbon atoms between the nitrogen atoms R-an aliphatic hydrocarbon radical of from about 400 to 5,000 average molecular weight a-an integer of from 0 to 10 ban integer of from 0 to 1 a+2b-an integer of from 1 to 10 c-an integer of from 1 to 5 and is as an average in the range of 1 to 4, and equal to or less than the number of nitrogen atoms in the molecule xan integer of from 0 to l y-an integer of from 0 to 1 The hydrocarbon radical indicated by R is relatively free of aliphatic unsaturation; that is, it will usually have not more than 2 sites of olefinic unsaturation and generally not more than 1 site of olefinic unsaturation and no acetylenic unsaturation.

The aliphatic hydrocarbon radical will ordinarily be prepared by polymerizing olefins of from 2 to 6 carbon atoms (ethylene being copolymerized with another olefin so as to provide a branched chain). The branched chain hydrocarbon radical will generally have at least 1 branch per 6 carbon atoms along the chain, preferably at least 1 branch per 4 carbon atoms along the chain and particularly preferred that there be at least 1 branch per 2 carbon atoms along the chain. That is, the preferred branched chain hydrocarbon radicals are polypropylene and polyisobutylene. The branches will be of from 1 to 2 carbon atoms usually, preferably 1 carbon atom, i.e., methyl.

In most instances, the compositions of this invention are not a pure single product, but rather a mixture of compounds having an average molecular weight. Usually, the range of molecular weights will be relatively narrow and peaked near the indicated molecular weight. Similary, for the more complicated polyamines, the compositions will be a mixture of amines having as the major product the compound indicated as the average composition and having minor amounts of analogous compounds relatively close in compositions to the dominant compound.

Monoamines The compositions which will be considered first are those where y is 0.

The monoamine compositions will have the following formula:

R NA X The above symbols are defined as follows:

R -a branched chain aliphatic hydrocarbon radical, usually of from about 425 to about 3,000 average molecular weight, preferably up to 1,500 molecular weight, and

particularly preferred of polypropylene or polyisobutylene A hydrogen, hydrocarbyl or hydroxyhydrocarbyl of from 1 to 10 carbon atoms, preferably aliphatic, and usually hydrogen; alkyl. or hydroxyalkyl of from 1 1 to 6 carbon atoms, more usually of from 1 to 3 carbon atoms X the same or different from A and hydrogen, hydrocarbyl or hydroxyhydrocarbyl of from 1 to 10 carbon atoms, preferably aliphatic, and usually hydrogen, alkyl or hydroxyalkyl of from 1 to 6 carbon atoms, more usually of from 1 to 3 carbon atoms A and X -when taken together with the nitrogen to which they are attached form a ring having 5 to 6 annular members, which may have from to 1 oxygen atom as an annular member to form, for example, morpholine.

Illustrative compositions include polypropenyl amine, polyisobutenyl amine, N-polyisobutenyl dimethylamine, N-polyisobutenyl methylethylamine, N-polypropenyl diethylamine, N-polypropenyl di(2-hydroxyethyl) amine, N-polyisobutenyl N-methyl aniline, N-polyisobutenyl morpholine, N-polyisobutenyl piperidine, Np0ly(l-butene) propylamine, N-polypropenyl N-(Z-hydroxyethyl) amine, etc.

The preferred monoamine compositions which find use in fuels have the following formula:

The above symbols are defined as follows:

R 'a branched chain aliphatic hydrocarbon radical, substantially free of olefinic unsaturation, of from about 420 to 1,250 average molecular weight A either hydrogen or lower alkyl, preferably of from 1 to 3 carbon atoms Polyamines The polyamine composition which find use in this invention are for the most part described by the following formula:

The above symbols are defined as follows:

U alkylene of from 2 to 6 carbon atoms, there being at least 2 carbon atoms between the nitrogen atoms and preferably of from 2 to 3 carbon atoms R an aliphatic hydrocarbon radical, usually a branched chain aliphatic hydrocarbon radical of from about 400 to 5,000 average molecular weight, preferably of from 400 to 3,000 average molecular weight a an integer of from 0 to 5 Il -an integer of from 0 to 1 a |2b an integer in the range of from 1 to 5 c -an integer of from 1 to 4, for the average composition being in the range of about 1 to 3, on the average there being fewer R groups than nitrogen atoms The alkylene radical indicated as U will have from 2 to 6 carbon atoms and more usually, from 2 to 3 carbon atoms, the nitrogen atoms connected by U being separated by at least 2 carbon atoms. The alkylene group may be straight chain or branched and is preferably polymethylene of from 2 to 3 carbon atoms.

Illustrative alkylene groups are ethylene, 1,2-propylene, 2,2-dirnethyl propylene-1,3, trimethylene, hexamethylene, 2-methyl-1,3-propylene, etc.

The alkylene polyamines which are substituted with the hydrocarbon radical may be derived from such alkylene amines as ethylene diamine, diethylene triamine, tetraethylene pentamine, nonaethylene decamine, Z-aminoethyl piperazine, 1,3-propylene diamine, 1,2-propylene diamine, tetramethylene diamine, etc.

As already indicated, in many instances a single compound will not be used as a reactant in the preparation of the compositions of this invention. That is, mixtures will be used in which one or two compounds will predominate and the average composition or molecular weight is indicated. For example, tetraethylene pentamine prepared by the polymerization of aziridine or reaction of dichloroethylene and ammonia Will have both lower and higher members, e.g., triethylene tetramine and pentaethylene hexamine, but the composition will be mainly tetraethylene pentamine and the empirical formula of the total composition will closely approximate that of tetraethylene pentamine. Similarly, the molecular weight reported for the branched chain aliphatic hydrocarbon group is an average for a mixture which is sharply peaked when graphing the number average molecular Weight distribution. Also, when the nitrogens of the alkylene polyamines are not equivalent, substitution on different nitrogens will afford different compounds.

As is evident from the above formulae, the alkylene polyamines may have only one hydrocarbon substituent or may be polysubstituted with hydrocarbon radicals. The mono-substituted alkylene polyamine compositions will have the following formula:

The above symbols are defined as follows:

a an integer of from 0 to 5, preferably of from 0 to 4 b -an integer of from 0 to 1, preferably 0 when a is greater than 0 a +2b an integer of from 1 to 5 d-an integer of from 2 to 3 R a branched chain aliphatic hydrocarbon radical derived from polymerizing olefins of from 2 to 6 carbon atoms, preferably of from 3 to 4 carbon atoms, and particularly preferred of propylene and isobutylene and having an average molecular weight in the range of 500 to 3,000, preferably 400 to 2,500

Illustrative compounds within the above formula are as follows: N-polyisobutenyl ethylene diamine, N-polypropenyl ethylene diamine, N-poly(1-butenyl) ethylene diamine, N-(alternating copolymer of ethylene and isobutylene) ethylene diamine (alternating copolymers of ethylene and isobutylene may be achieved by the cationic polymerization of 4-methylpentene-1), N-polypropenyl Z-aminoethylpiperazine, N-polyisobutenyl Z-aminoethylpiperazine, N-polypropenyl diethylene triamine, N-polyisobutenyl diethylene triamine, N-poly(1-pentenyl) diethylene triamine, N-polypropenyl trimethylene diamine, N- polyisobutenyl trimethylene diamine, N-polypropenyl di- (trimethylene) triamine, N-polyisobutenyl di(trimethylene) triamine, N-polyisobutenyl 1,2-propylene diamine, N-polyisobutenyl di(l,2-propylene) triamine, N-polypropenyl triethylene tetramine, N-polyisobutenyl triethylene tetramine, N-( alternating copolymer of ethylene and isobutylene) triethylene tetramine, N-polypropenyl tetraethylene pentamine, N-polyisobutenyl tetraethylene pentamine, N-polyisobutenyl pentaethylene hexamine, etc.

The polyhydrocarbon radical substituted alkylene polyamine compositions have the following formula:

The above symbols are defined as follows:

preferably of from 400 to about 2,500 average molecular weight (As indicated by the above formula, the number of hydrocarbon substituents need not be a whole number when averaged over the total composition; generally, a mixture will be obtained containing mono-, diand trior higher substituted molecules averaging out to a fractional or whole number.)

Illustrative compounds coming within the above formula are as follows: N,Ndi(polypropenyl) diethylene triamine, N,Ndi(polyisobutenyl) diethylene triamine, N,N-di(polyisobutenyl) triethylene tetramine, N,N'-di- (polypropenyl) tetraethylene pentamine, N'N-di(polyisobutenyl) tetraethylene pentamine, N,N',N"-tri(polyiso butenyl) tetraethylene pentamine, N,N-di(polyisobutenyl) Z-aminoethylpiperazine, N,N-di(poly-1-butenyl) triethylene tetramine, N,N'-di(polyisobutenyl) di(trimethylene) triamine, etc.

The preferred compositions are those having the straight chain alkylene polyamines, particularly ethylene diamine and polyethylene polyarnines. These compositions have the following formula:

[bII 2 2 I") n ]R H3+ L The above symbols are defined as follows:

a an integer of from 1 to 5, preferably of from 1 to 4 c -an integer in the range of 1 to 3, on the average over the entire composition being in the range of from 1 to 2, per molecule there being fewer R groups than nitrogen atoms R -a brached chain aliphatic hydrocarbon radical of from 400 to 3,000 average molecular weight, preferably of from 400 to 2,500 average molecular weight, and, particularly preferred, either polypropenyl or polyisobutenyl Particularly preferred fuel detergent compositions have the following formula:

a an integer of from 1 to 3 c -an integer of from 1 to 3, averaging over the entire composition in the range of 1 to 2 R a branched chain aliphatic hydrocarbon radical of from about 420 to 1,500 average molecular weight, preferably polypropylene or polyisobutylene Synthesis The compositions of this invention are readily prepared by combining an aliphatic or alicyclic halide with the desired amine in the proper mole proportions. The halide is prepared from the hydrocarbon by halogenation: ionically or free radically.

As already indicated, the hydrocarbon groups may be prepared by ionic or free radical polymerization of olefins of from 2 to 6 carbon atoms (ethylene must be copolymerized with another olefin) to an olefin of the desired molecular weight. The olefins which find use are ethylene, propylene, isobutylene, l-butene, l-pentene, 3- methyl-l-pentene, 4-methyl-l-pentene, etc., preferably propylene and iso-butylene.

As previously indicated, there should be at least 1 branch per 6 carbon atoms along the chain and preferably at least 1 branch per 4 carbon atoms along the chain. The preferred olefins, propylene and isobutylene, have from 0.5 to 1 branch per atom along the hydrocarbon chain.

The halogen may be introduced into the hydrocarbon molecule by various means known in the art. Most readily, either chlorine or bromine (halogen of atomic number 17-35) may be introduced by the free radical catalyzed halogenation of the hydrocarbon, or ionic addition to olefinic unsaturation. Various free radical catalysts may be used, such as peroxides, azo compounds, bromine, iodine, as Well as light. Ionic catalysts are exemplified by ferric chloride. Methods of halogenation are well known in the art and do not require extensive exemplification or illustration here.

The amount of halogen introduced will depend on the particular hydrocarbon used, the desired amount of amine to be introduced into the molecule, the particular alkylene amine used, and the halogen used. The amount of halogen introduced will generally be in the range from about 1 to 5 halogen atoms per molecule, depending on the reactivity of the resulting halide. On a weight percent basis, the amount of halide will generally range from about 1 to 25, more usually from about 1 to 10.

The halohydrocarbon and amine may be brought together neat or in the presence of an inert solvent, particularly a hydrocarbon solvent. The inert hydrocarbon solvent may be aliphatic or aromatic. Also, aliphatic alcohols may be used by themselves or in combination with another solvent, when capable of dissolving the reactants.

The reaction may be carried out at room temperature (20 C.), but elevated temperatures are preferred. Usually, the temperature will be in the range: of from about to 225 C. Depending on the temperature of the reaction, the particular halogen used, the mole ratios and the particular amine, as well as the reactant concentrations, the time may vary from 1 to 24 hours, more usually from about 3 to 20 hours. Times greatly in excess of 24 hours do not particularly enhance the yield and may lead to undesirable degradation. It is therefore preferred to limit the reaction time to fewer than 24 hours.

The mole ratio of halohydrocarbon to amine will generally be in the range from about 0.2 to 20 moles of amine per mole of halohydrocarbon, more usually 0.5 to 10 moles of amine per mole of halohydrocarbon. The mole ratio will depend upon the amount of halogen present in the halohydrocarbon, the particular halogen and the desired ratio of hydrocarbon to amine. If complete suppression of polysubstitution of the alkylene polyamines is desired, then large mole excesses of the amine will be used.

Small amounts of residual halogen in the final composition are not deleterious. Generally, the residual halogen as bound halogen will be in the range of 0 to 10 weight percent of the composition. Small amounts of halogen may be present as the hydrohalide salt of the hydrocarbon substituted alkylene polyamines.

Generally, the hydrocarbons used will have aliphatic unsaturation. In particular instances, the amines may react in a way resulting in the elimination of hydrogen halide, introducing further aliphatic unsaturation into the hydrocarbon radical. Therefore, the hydrocarbon radicals usually will be olefinically unsaturated. However, the olefinic unsaturation does not significantly affect the utility of the product, and when available, saturated aliphatic halide may be used.

After the reaction has been carried out for a sufficient length of time, the reaction mixture may be extracted with a hydrocarbon medium to free the product from any low molecular weight amine salt which has formed. The product may then be isolated by evaporation of the solvent. Further separation from unreacted hydrocarbon or purification may be carried out as desired, e.g., chromatography.

Depending on the particular application of the composition of this invention, the reaction may be carried out in the medium in which it will ultimately find use and be formed at concentrations which provide a concentrate of the detergent composition. Thus, the final mixture may be in a form to be used directly upon dilution in fuels.

The detergent will generally be employed in a hydrocarbon base liquid fuel. The detergent additive may be formulated as a concentrate, using a suitable hydrocarbon alcohol solvent boiling in the range of about to 400 F. Preferably, an aromatic hydrocarbon solvent is used, such as benzene, toluene, xylene or higher boiling aromatics or aromatic thinners. Aliphatic alcohols of about 3 to 8 carbon atoms, such as isopropanol, isobutylcarbinol, n-butanol and the like, in combination with hydrocarbon solvents are also suitable for use with the detergent additive. In the concentrate, the amount of the additive will be ordinarily at least 10 percent by weight and generally not exceed 70 percent by weight.

The amount of the detergent used in the fuel will generally be from about 100 to 1,000 ppm.

In gasoline fuels, other fuel additives may also be included such as antiknock agents, e.g., tetramethyl lead or tetraethyl lead. Also included may be lead scavengers such as aryl halides, e.g., dichlorobenzene or alkyl halides, e.g., ethylene dibromide.

A nonvolatile lubricating mineral oil, e.g., petroleum spray oil, particularly a refined naphthenic lubricating oil having a viscosity at 100 F. of 1,000 to 2,000 SUS, is a suitable additive for the gasoline compositions used with the detergents of this invention and its use is preferred. These oils are believed to act as a carrier for the detergent and assist in removing and preventing deposits. They are employed in amounts from about 0.05 to 0.5 percent by volume, based on the final gasoline composition.

The following examples are ofifered by way of illustration and not by way of limitation.

Example A Into a reaction flask was introduced 950 g. of polyisobutylene (approximate molecular weight=950) dissolved in 1,000 ml. of carbon tetrachloride. The mixture was stirred and chlorine was introduced at a rate of 235-250 ml. per minute, the temperature being maintained at 0 C. After the reaction mixture had taken up 51 g. of chlorine, the introduction of chlorine was terminated, the carbon tetrachloride removed in vacuo and the chlorinated polyisobutylene isolated and analyzed. Analysis: wt. percent chlorine, 7.0.

Example B Into a reaction flask was introduced 225 g. of N-bromosuccinimide, 750 g. of polyisobutylene (approximately 930 average molecular weight) and 750 ml. of carbon tetrachloride, the flask swept with nitrogen and the solution heated to 70 C. while maintaining a positive nitrogen pressure on the flask. To the solution was then added dropwise 0.5 g. of benzoyl peroxide in 50 ml. of carbon tetrachloride. At the end of the addition, the solution was cooled and the succinimide filtered off. The carbon tetrachloride was removed in vacuo. Analysis: wt. percent bromine, 8.86, 8.80.

Example 1 Into a reaction flask was charged 1,156 g. of chloropolyisobutylene (polyisobutylene of approximately 950 molecular weight chlorinated to 7.8 weight percent chlorine), 75 ml. of xylene and 330 ml. of ethylene diamine, followed by the addition of 330 ml. of n-butanol. The mixture was then raised to a temperature of 100 C. over one hour and the temperature was then raised to about 160 C. and maintained there for about 4 /2 hours. About 330 ml. of distillate was obtained while raising the temperature from 130 to 160 C. The reaction mixture was transferred to a separatory funnel with the aid of one liter of benzene, and the mixture washed repeatedly first with a dilute aqueous solution of isopropyl alcohol, then with a dilute aqueous solution of a combination of isopropyl alcohol and butanol and finally with water. The volatile materials were then removed from a sample of the washed product by sparging with nitrogen to constant weight on a steam plate. Analysis: titrimetric equivalent wt., 806, equal to 1.74% N; wt. percent chlorine, 0.62.

One thousand four hundred thirty-four g. or about half of the volatile solvents was removed from the main portion of the washed product. This solution containing about 25% volatile solvent (titrimetric equivalent weight: 1,051)

Example 2 Into a reaction flask was introduced 1,000 g. of chloropolyisobutene (polyisobutene of approximately 420 molecular weight chlorinated to approximately 8 weight percent chlorine), 270 ml. of ethylene diamine and 270 ml. of n-butanol. The mixture was heated gradually to 170 C. during 1 /2 hours; distillate was collected mainly between C. and C. The mixture was then heated for about 3 hours at C. At the end of this time, 1,000 ml. of toluene and 250 ml. of methyl isobutyl carbonol were added and the mixture washed with dilute aqueous isopropyl alcohol followed by repeated washings with water. Some of the volatile solvents were then removed on a steam bath using a nitrogen stream. The combined products from two similar runs were then filtered, yielding 3,911 g. Analysis: titrimetric equivalent wt., 840, equal to 1.67 wt. percent N. Complete removal of volatile solvents from a small sample indicated the product contains about 40% solvents, i.e., toluene and methyl isobutyl carbinol.

Example 3 Following the procedure of Example 2, 1,000 g. of chloropolypropylene (polypropylene of about 800 molecular weight chlorinated to about 6 weight percent chlorine) was reacted with 270 g. of ethylene diamine. The product as finished contained about 15% volatile solvents. Analysis: titrimetric equivalent wt., 1,080, equal to 1.3 Wt. percent N.

Example 4 Into a reaction flask was introduced 1,500 g. of chloropolyisobutylene (polyisobutylene of approximately 950 molecular weight chlorinated to 5.6 weight percent chlorine), 285 g. of alkylene polyamine having an average composition of tetraethylene pentamine and 1,200 m1. of benzene, the mixture heated to reflux, followed by stripping otf the benzene and heating the mixture at about 170 C. for about 4 hours. The mixture was then allowed to cool, diluted with equal volumes of mixed hexanes and absolute ethanol, heated to reflux and /3 volume of 10 weight percent aqueous sodium carbonate added. The phases were separated, and the organic phase washed with water, followed by removing the volatile materials in vacuo. Analysis: wt. percent N, 4.15, 4.15; molecular weight (ThermoNam), 1,539.

Example 5 Following the procedure of Example 2, 950 g. of chloropolyisobutylene (polyisobutylene of approximately 950 molecular Weight chlorinated to 4.48 weight percent chlorine) was combined with 270 ml. of ethylene diamine in 270 ml. of n-butanol. The product as finished contained about 20 percent volatile solvents. Analysis: titrimetric equivalent wt., 976, equal to 1.44 wt. percent N.

Example 6 Into a high pressure bomb was introduced 1,200 g. of polyisobutenyl chloride (approximately 500 molecular weight, wt. percent chlorine, -8) and 400 g. of liquid ammonia, the bomb sealed and heated at 150 C. with rocking for about 15 hours. After cooling, the pressure was vented and the reaction mixture taken up in mixed hexanes, water and alcohol. The organic phase was then washed with 500 ml. of 5 percent sodium hydroxide, followed by repeated washings with water. The solvents ware then distilled off and the residue, which weighed 767 g., filtered through Celite.

Titration of the product showed an equivalent weight of 1,090, indicating that the material was 40 percent active (contained 40 percent by weight of polyisobutenyl amine).

9 10 In order to demonstrate the effectiveness of the com- We claim: positions of this invention as detergents and dispersants 1. A fuel composition having a major amount of a in fuels, both extended detergent action performance and hydrocarbonaceous liquid fuel and in an amount to proharm tests were carried out. In the extended detergent vide detergency and dispersancy, a composition having a action performance test, the ability of the detergent to molecular weight in the range of 425 to 10,000 of the act to prevent deposits throughout the intake system is formula:

determined, while in the harm test, the formation of I I deposits by the detergent is investigated. ({AXNhi-Nfl-UN-M-UN s N}b)}y)RoHH-2y+ayo In carrying out the performance test, a 1953 Chevrolet 6-cylinder engine is used, starting with clean cylinder head Whercin and intake system. The run is carried out for 200 hours A is hydrogen, hydrocarbyl of from 1 to 10 carbon under cyclic conditions, at the end of which time the atoms or hydroxyhydrocarbyl of from 1 to 10 carbon head and intake system are disassembled and all intake atoms,

areas from the carburetor to and including the intake X is hydrogen, hydrocarbyl of from 1 to 10 carbon valves are inspected. The conditions under which the run atoms or hydroxyhydrocarbyl of from 1 to 10 carbon is carried out are as follows: Jacket temperature: 185 atoms and may be taken together with A and the F.; oil temperature: 185 F.; cycle: idle at 600 rpm. nitrogen to which A and X are attached to form a 31% of the time, acceleration 16% of the time, cruise at ring of from 5 to 6 annular members having from 1,500 rpm. or 2,500 r.p.m. 26% of the time, and 0 to 1 oxygen annular member, 1 nitrogen annular deceleration 27% of the time. In evaluating the engine, member and from 4 to 5 carbon annular members, port and valve deposits are rated on a scale of 0 (clean) U is alkylene of from 2 to 6 carbon atoms, there being to 10 (very heavy deposits) and valve deposit weights at least 2 carbon atoms between the nitrogen atoms, determined. The remainder of the intake system is rated R is an aliphatic hydrocarbon radical or from about on a linear scale of 0 (clean) to 16 (deposit thick). 400 to 5,000 average molecular weight,

Also, any stuck intake valves are observed and reported. a is an integer of from (Ho 10,

The harm test is carried out on a 1960 Chevrolet 6- b is an integer of from (Ho 1, cylinder engine. Starting with a clean cylinder head, ina+2b is an integer of from 1 to 10, take system, pistons and new rings, the test is carried out 6 is an integer of from 1 to 5 and equal to or less than for 200 hours under cyclic conditions. At the end of this th b f nitrogen atoms i h l l time, the engine is disassembled and the parts are inxis an integer of fromOto l, spected. The conditions under which the run is carried y is an integer of from 0 t0 1, and out are as follows: Jacket temperature: 200 F.; oil temx+y is equal to 1, perature: 125 F.; cycle: idle at 600 r.p.m. of the 2. A fuel com-position according to claim 1, wherein time, low speed acceleration 20% of the time, high speed i .0, a c l ratiml 13% 0f the time, and Cruise at 1,400 -p- 3 R is a branched chain aliphatic hydrocarbon radical of 27% of the time. The rating is as follows: port and valve f om 400 t 3,000 mole ula weight, deposits are rated on a scale of 0 (clean) to 10 (very U is alkylene of from 2 to 3 carbon atoms, heavy deposits). The percent of oil ring plugging is measa i a integer of from to 5, ured. The piston varnish is rated on a scale of 0 to 10, a+2bi an integer in the range of 1 to 5, and with 10 as cleany, y stuck intake valves and 4.0 c is an integer of from 1 to 4 and equal to or less than pistonrings are reported. the number of nitrogen atoms in the .molecule.

The following table indicates the results of both the 3, A f l iti according t l im 2, wherein performance and the harm test described above using 250 U is polymethylene of from 2 to 3 carbon atoms, and ppm. of the detergent additive. o i 1,

TABLE.-EXTENDED DETERGENT ACTION TESTS Performance test Harm test Additive Wt. example percent Valve Valve Port Intake Stuck Valve Port Oil ring Piston Stuck Stuck oil 1 rating vdgpgsrilg, rating system valves rating rating plugging varnish valves rings 1 A solvent refined neutral oil, 2L9 API gravity, viscosity at 100 F., 1,685 SUS, viscosity at 210 F., 87 SUS. 2 Average of two base fuel runs.

The data graphically demonstrate the excellent eifec- 4.. A fuel composition according to claim 2, wherein tiveness of the compositions of this invention. The compo- U is polymethylene of from 2 to 3 carbon atoms, and sitions are excellent detergents, without having serious 0 is greater than 1 and equal to or less than 3. detrimental side effects. The detergent compositions are 5.. A fuel composition according to claim 1, having readily available by simple synthetic methods, do not from 0.05 to 0.5% by volume of a mineral lubricating oil. produce ash in the engine and either do not or only to an 6. A fuel composition according to claim 2, having insignificant degree create deposits from their own defrom 0.0-5 to 0.5 by volume of a mineral lubricating oil. composition products. Moreover, the detergents are eflfec- 7. A fuel composition according to claim 2, wherein tive in cleaning the ports, valves and intake system, so said composition to provide detergency and dispersancy as to provide extended detergent action. Also, good water is of the formula: tolerance can be achieved. 7 I I As will be evident to those skilled in the art, various 4 modifications on this invention can be made or followed, N (CHQOHZN )ufilmo HMS in the light of the foregoing disclosure and discussion, wherein a is an integer of from 1 to 3; c is an integer without departing from the spirit or scope of the disof from 1 to 3, averaging over the entire composition in closure or from the scope of the following claims. the range of 1 to 2, and R is a branched. chain aliphatic hydrocarbon radical of from about 420 to 1,500 average molecular Weight.

8. A fuel composition according to claim 7, wherein R is polyisobutylene.

9. A fuel composition according to claim 7, having from 0.05 to 0.5 percent 'by volume of a mineral lubricating oil.

10. A fuel composition having a major amount of a hydrocarbonaceous liquid fuel and in an amount to provide detergency and dispersancy, a composition of the formula:

R NA X wherein R is a branched chain aliphatic hydrocarbon radical of from about 425 to about 3,000 molecular weight,

A is hydrogen, hydrocarbyl or hydroxyhydrocarbyl of from 1 to 10 carbon atoms, and

X is hydrogen, hydrocarbyl or hydroxyhydrocarbyl of from 1 to 10 carbon atoms and may be taken together with A and the nitrogen to which A and X are attached to form a ring of from 5 to 6 annular members, having from 0 to 1 oxygen annular member, 1 nitrogen annular member and from 4 to 5 carbon annular members.

11. A fuel composition according to claim 10, wherein A and X are hydrogen or alkyl of from 1 to 6 carbon atoms.

12. A fuel composition according to claim 10, having from 0.05 to 0.5% by volume of a mineral lubricating oil.

References Cited UNITED STATES PATENTS 3,050,043 8/1962 Bamlsch 4472 XR 3,231,348 1/1966 Lindstrom et a1. 4472 3,275,554 9/1966 Wagenaar 25250 PATRICK P. GARVIN, Primary Examiner.

US. Cl. X.R.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US3050043 *Apr 1, 1960Aug 21, 1962California Research CorpOperation of spark-ignition engines
US3231348 *Dec 7, 1961Jan 25, 1966Chevron ResGasoline fuel containing substituted diethylenetriamines
US3275554 *Mar 17, 1964Sep 27, 1966Shell Oil CoPolyolefin substituted polyamines and lubricants containing them
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3671511 *Apr 23, 1970Jun 20, 1972Eddie G LindstromProcess for preparing polyolefin-substituted amines
US3717446 *Dec 31, 1970Feb 20, 1973Union Oil CoGasoline anti-icing additives (a)
US3753670 *Jun 30, 1970Aug 21, 1973Shell Oil CoHydrocarbon fuel compositions
US3767574 *Dec 6, 1971Oct 23, 1973Phillips Petroleum CoGasoline additive
US3852258 *Dec 18, 1972Dec 3, 1974Chevron ResProcess for preparing polyolefin substituted amines
US3876704 *Aug 9, 1973Apr 8, 1975Union Oil CoDetergent automotive fuel composition
US3884647 *Aug 9, 1973May 20, 1975Union Oil CoDetergent automotive fuel composition
US3898056 *Oct 11, 1973Aug 5, 1975Chevron ResHydrocarbylamine additives for distillate fuels
US3907518 *Sep 19, 1973Sep 23, 1975Rohm & HaasDetergent motor fuel
US3912641 *Sep 27, 1973Oct 14, 1975Lubrizol CorpSulfur and nitrogen-containing organic compositions processes for making them and fuels and additives containing them
US3960515 *Feb 19, 1974Jun 1, 1976Chevron Research CompanyHydrocarbyl amine additives for distillate fuels
US3996024 *Jun 22, 1973Dec 7, 1976Chevron Research CompanyFuel composition
US4022589 *Oct 17, 1974May 10, 1977Phillips Petroleum CompanyFuel additive package containing polybutene amine and lubricating oil
US4039300 *Jun 3, 1974Aug 2, 1977Atlantic Richfield CompanyGasoline fuel composition and method of using
US4065499 *Sep 15, 1975Dec 27, 1977Ethyl CorporationLubricant additive
US4082518 *Apr 28, 1975Apr 4, 1978Phillips Petroleum CompanyAdditives for motor fuels and lubricants
US4128403 *Jun 29, 1976Dec 5, 1978Chevron Research CompanyFuel additive for distillate fuels
US4160648 *May 27, 1977Jul 10, 1979Chevron Research CompanyFuel compositions containing deposit control additives
US4191537 *Jun 19, 1978Mar 4, 1980Chevron Research CompanyFuel compositions of poly(oxyalkylene) aminocarbamate
US4200518 *Mar 22, 1979Apr 29, 1980Chevron Research CompanyHeat exchanger anti-foulant
US4233168 *Jun 19, 1978Nov 11, 1980Chevron Research CompanyLubricant compositions containing dispersant additives
US4236020 *Jun 18, 1979Nov 25, 1980Chevron Research CompanyCarbamate deposit control additives
US4288612 *Apr 28, 1980Sep 8, 1981Chevron Research CompanyDeposit control additives
US4330302 *Aug 28, 1975May 18, 1982Exxon Research & Engineering Co.High thermal stability liquid hydrocarbons and methods for producing them
US4505718 *Aug 20, 1982Mar 19, 1985The Lubrizol CorporationOrgano transition metal salt/ashless detergent-dispersant combinations
US4852993 *Aug 12, 1987Aug 1, 1989Texaco Inc.ORI-inhibited and deposit-resistant motor fuel composition
US4859210 *Jan 5, 1988Aug 22, 1989Basf AktiengesellschaftMotor fuel or lubricant composition containing polybutyl or polyisobutyl derivatives
US4863487 *Apr 29, 1987Sep 5, 1989Nalco Chemical CompanyHydrocarbon fuel detergent
US4865621 *Jan 27, 1989Sep 12, 1989Texaco Inc.Ori-inhibited and deposit-resistant motor fuel composition
US4877416 *Nov 18, 1987Oct 31, 1989Chevron Research CompanySynergistic fuel compositions
US4895578 *Sep 8, 1988Jan 23, 1990Nalco Chemical CompanyHydrocarbon fuel detergent
US4968321 *Feb 6, 1989Nov 6, 1990Texaco Inc.ORI-inhibited motor fuel composition
US4973336 *Aug 11, 1989Nov 27, 1990Gheysens Jean Louis GFuel additives
US5006130 *Jun 28, 1989Apr 9, 1991Shell Oil CompanyGasoline composition for reducing intake valve deposits in port fuel injected engines
US5211721 *Jul 15, 1991May 18, 1993Texaco Inc.Polyoxyalkylene ester compounds and ORI-inhibited motor fuel compositions
US5242469 *May 30, 1991Sep 7, 1993Tonen CorporationGasoline additive composition
US5292444 *Oct 2, 1992Mar 8, 1994Exxon Research And Engineering CompanyLube oil compositions containing fullerene-grafted polymers
US5292813 *Oct 2, 1992Mar 8, 1994Exxon Research & Engineering Co.Fullerene-grafted polymers and processes of making
US5334329 *Oct 7, 1988Aug 2, 1994The Lubrizol CorporationLubricant and functional fluid compositions exhibiting improved demulsibility
US5352251 *Mar 30, 1993Oct 4, 1994Shell Oil CompanyFuel compositions
US5405418 *May 2, 1994Apr 11, 1995Chevron Chemical CompanyFuel additive compositions containing an aliphatic amine, a polyolefin and an aromatic ester
US5405419 *May 2, 1994Apr 11, 1995Chevron Chemical CompanyFuel additive compositions containing an aliphatic amine, a polyolefin and a poly(oxyalkylene) monool
US5430105 *Nov 22, 1993Jul 4, 1995Exxon Chemical Patents Inc.Low sediment process for forming borated dispersant
US5455358 *Feb 9, 1994Oct 3, 1995Chevron U.S.A. Inc.Fuel compositions containing alkyl-substituted cyclic urea-substituted amines
US5457211 *Feb 10, 1994Oct 10, 1995Chevron U.S.A. Inc.Hydroxyalkyl-substituted cyclic urea-substituted amines
US5458660 *Sep 19, 1994Oct 17, 1995Shell Oil CompanyFuel compositions
US5458661 *Sep 19, 1994Oct 17, 1995Shell Oil CompanyFuel compositions
US5462567 *Dec 28, 1992Oct 31, 1995Chevron Chemical CompanyFuel additive compositions containing poly(oxyalkylene)hydroxyaromatic esters and aliphatic amines
US5478367 *Oct 11, 1991Dec 26, 1995Exxon Chemical Patents Inc.Fuel oil compositions
US5489315 *Sep 19, 1994Feb 6, 1996Shell Oil CompanyFuel compositions comprising hydantoin-containing polyether alcohol additives
US5492641 *Nov 21, 1994Feb 20, 1996Basf Aktiengesellschaftβ-aminonitriles and N-alkyl-1,3-propylenediamines and their use as fuel additives and lubricant additives
US5498809 *May 22, 1995Mar 12, 1996Exxon Chemical Patents Inc.Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5507843 *Sep 19, 1994Apr 16, 1996Shell Oil CompanyFuel compositions
US5516342 *Dec 28, 1992May 14, 1996Chevron Chemical CompanyFuel additive compositions containing poly(oxyalkylene) hydroxyaromatic ethers and aliphatic amines
US5554310 *Jun 9, 1994Sep 10, 1996Exxon Chemical Patents Inc.Trisubstituted unsaturated polymers
US5663130 *Mar 11, 1996Sep 2, 1997Exxon Chemical Patents IncPolymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5674950 *Feb 27, 1995Oct 7, 1997Exxon Chemical Patents Inc.Polymers having terminal hydroxyl aldehyde, or alkylamino substitutents and derivatives thereof
US5691422 *Jun 12, 1996Nov 25, 1997Exxon Chemical Patents Inc.Saturated polyolefins having terminal aldehyde or hydroxy substituents and derivatives thereof
US5693107 *Aug 6, 1996Dec 2, 1997Shell Oil CompanyFuel compositions comprising hydantoin-containing polyether alcohol additives
US5752989 *Nov 21, 1996May 19, 1998Ethyl CorporationDiesel fuel and dispersant compositions and methods for making and using same
US5755832 *Nov 7, 1996May 26, 1998Chevron Chemical CompanyFuel additive concentrate containing tagging material
US5755835 *Dec 28, 1992May 26, 1998Chevron Chemical CompanyFuel additive compositions containing aliphatic amines and polyalkyl hydroxyaromatics
US5777041 *Jan 22, 1997Jul 7, 1998Exxon Chemical Patents IncSaturated polyolefins having terminal aldehyde or hydroxy substituents and derivatives thereof
US5780554 *Nov 1, 1996Jul 14, 1998Exxon Chemical Patents Inc.Saturated polyolefins having terminal aldehyde or hydroxy substituents and derivatives thereof
US5811379 *Jun 17, 1996Sep 22, 1998Exxon Chemical Patents Inc.Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US5814111 *Aug 6, 1996Sep 29, 1998Shell Oil CompanyGasoline compositions
US5837867 *Aug 6, 1996Nov 17, 1998Shell Oil CompanyFuel compositions
US5855630 *Sep 19, 1997Jan 5, 1999Shell Oil CompanyFuel compositions
US5858929 *Dec 21, 1995Jan 12, 1999The Lubrizol CorporationComposition for providing anti-shudder friction durability performance for automatic transmissions
US5880219 *Apr 8, 1997Mar 9, 1999Exxon Chemical Patents Inc.Polymers having terminal hydroxyl, aldehyde, or alkylamino substituents and derivatives thereof
US5919869 *Mar 6, 1998Jul 6, 1999Exxon Chemical Patents, Inc.Polymers having terminal hydroxyl, aldehyde, or alkylamino substituents and derivatives thereof
US5945388 *Aug 21, 1994Aug 31, 1999Lubrizol Adibis Holdings (Uk) Ltd.Lubricating oil compositions
US5993499 *Jun 27, 1997Nov 30, 1999Chevron Chemical CompanyFuel composition containing an aliphatic amine and a poly (oxyalkylene) monool
US6030930 *May 14, 1997Feb 29, 2000Exxon Chemical Patents IncPolymers derived from ethylene and 1-butene for use in the preparation of lubricant disperant additives
US6034184 *Jun 23, 1998Mar 7, 2000Mobil Oil CorporationDispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: Mannich reaction products
US6054539 *Jul 31, 1998Apr 25, 2000Mobil Oil CorporationSelectively hydrogenated polymer compositions: polybutadiene-isoprene-polybutadiene
US6066603 *Jul 21, 1997May 23, 2000Exxon Chemical Patents Inc.Polar monomer containing copolymers derived from olefins useful as lubricant and useful as lubricant and fuel oil additivies process for preparation of such copolymers and additives and use thereof
US6069281 *Jul 4, 1996May 30, 2000Basf AktiengesellschaftProcess for producing organic nitrogen compounds, special organic nitrogen compounds and mixtures of such compounds and their use as fuel and lubricant additives
US6071319 *Dec 22, 1998Jun 6, 2000Chevron Chemical Company LlcFuel additive compositions containing aromatic esters of polyalkylphenoxyalkanols and aliphatic amines
US6090170 *Dec 31, 1998Jul 18, 2000Daelim Industrial Co., Ltd.Multihydroxypolyalkenyl-substituted amine compounds and fuel composition comprising the same
US6103676 *Jun 23, 1998Aug 15, 2000Mobil Oil CorporationDispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: hydroformylation/reductive amination reaction products
US6136051 *Jul 5, 1996Oct 24, 2000Chevron Chemical CompanyMethod and composition for reduction of combustion chamber deposits
US6162768 *Jun 23, 1998Dec 19, 2000Mobil Oil CorporationDispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: free radically initiated direct grafting reaction products
US6172015Jul 21, 1999Jan 9, 2001Exxon Chemical Patents, IncPolar monomer containing copolymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such copolymers and additives and use thereof
US6215033Dec 11, 1998Apr 10, 2001Mobil Oil CorporationDispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: blends with lower molecular weight components
US6228817Jun 23, 1998May 8, 2001Mobil Oil CorporationDispersants and dispersant viscosity index improvers from selectively hydrogenated polymers
US6248702Nov 30, 1998Jun 19, 2001Mobil Oil CorporationDispersant and dispersant viscosity index improvers from selectively hydrogenated aryl-substituted olefin containing diene copolymers
US6261327May 28, 1998Jul 17, 2001Shell Oil CompanyAdditive concentrates for rapidly reducing octane requirement
US6299655 *Jun 30, 1993Oct 9, 2001The Lubrizol CorporationDiesel fuel compositions
US6312481Oct 9, 1997Nov 6, 2001Shell Oil CompanyFuel compositions
US6319881Jul 12, 1999Nov 20, 2001Exxonmobil Oil CorporationHaze free oil additive compositions containing dispersants from selectively hydrogenated diene copolymers
US6346129Feb 6, 1995Feb 12, 2002Chevron Oronite Company LlcFuel compositions containing hydroxyalkyl-substituted polyamines
US6368370Feb 6, 1995Apr 9, 2002Chevron Oronite Company LlcFuel compositions containing hydroxyalkyl-substituted amines
US6468948Jul 21, 1999Oct 22, 2002Infineum Usa L.P.Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US6488723Feb 2, 2001Dec 3, 2002Alfred Richard NelsonMotor fuel additive composition and method for preparation thereof
US6573223Mar 4, 2002Jun 3, 2003The Lubrizol CorporationLubricating compositions with good thermal stability and demulsibility properties
US6627584Jan 28, 2002Sep 30, 2003Ethyl CorporationAutomatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids
US6638324Feb 26, 2002Oct 28, 2003Oryxe Energy International, Inc.Organic cetane improver
US6660050May 23, 2002Dec 9, 2003Chevron U.S.A. Inc.Method for controlling deposits in the fuel reformer of a fuel cell system
US6689723Mar 5, 2002Feb 10, 2004Exxonmobil Chemical Patents Inc.Sulfide- and polysulfide-containing lubricating oil additive compositions and lubricating compositions containing the same
US6776897Oct 19, 2001Aug 17, 2004Chevron U.S.A.Thermally stable blends of highly paraffinic distillate fuel component and conventional distillate fuel component
US6824671May 17, 2001Nov 30, 2004Exxonmobil Chemical Patents Inc.Low noack volatility poly α-olefins
US6827750Aug 24, 2001Dec 7, 2004Dober Chemical CorpControlled release additives in fuel systems
US6835218Aug 24, 2001Dec 28, 2004Dober Chemical Corp.Fuel additive compositions
US6846402Oct 19, 2001Jan 25, 2005Chevron U.S.A. Inc.Thermally stable jet prepared from highly paraffinic distillate fuel component and conventional distillate fuel component
US6860241Aug 24, 2001Mar 1, 2005Dober Chemical Corp.Fuel filter including slow release additive
US6869917Aug 16, 2002Mar 22, 2005Exxonmobil Chemical Patents Inc.Functional fluid lubricant using low Noack volatility base stock fluids
US6878676May 8, 2001Apr 12, 2005Crompton CorporationNanosized particles of molybdenum sulfide and derivatives, method for its preparation and uses thereof as lubricant additive
US6949688Oct 6, 2004Sep 27, 2005Exxonmobil Chemical Patents Inc.Low Noack volatility poly α-olefins
US7001531Aug 24, 2001Feb 21, 2006Dober Chemical Corp.Sustained release coolant additive composition
US7029506Jun 12, 2002Apr 18, 2006Jordan Frederick LOrganic cetane improver
US7033484Jun 25, 2004Apr 25, 2006Chevron U.S.A. Inc.Thermally stable blends of highly paraffinic distillate fuel component with conventional distillate fuel component
US7141083Feb 26, 2002Nov 28, 2006Oryxe Energy International, Inc.Method and composition for using organic, plant-derived, oil-extracted materials in resid fuel additives for reduced emissions
US7144433Feb 26, 2002Dec 5, 2006Oryxe Energy International, Inc.Method and composition for using organic, plant-derived, oil-extracted materials in fossil fuels for reduced emissions
US7144434Feb 26, 2002Dec 5, 2006Oryxe Energy International, Inc.Method and composition for using organic, plant-derived, oil-extracted materials in coal-based fuels for reduced emissions
US7144435Feb 26, 2002Dec 5, 2006Oryxe Energy International, Inc.Method and composition for using organic, plant-derived, oil-extracted materials in two-cycle oil additives for reduced emissions
US7160338Feb 26, 2002Jan 9, 2007Oryxe Energy International, Inc.Method and composition for using organic, plant-derived, oil-extracted materials in jet fuels for reduced emissions
US7160339Feb 26, 2002Jan 9, 2007Oryxe Energy International, Inc.Method and composition for using organic, plant-derived, oil-extracted materials in gasoline additives for reduced emissions
US7220289Feb 26, 2002May 22, 2007Oryxe Energy International, Inc.Method and composition for using organic, plant-derived, oil-extracted materials in diesel fuel additives for reduced emissions
US7320748Sep 13, 2004Jan 22, 2008Chevron U.S.A. Inc.Thermally stable jet prepared from highly paraffinic distillate fuel component and conventional distillate fuel component
US7581558Jun 5, 2007Sep 1, 2009Cummins Filtration Ip Inc.Controlled release of additives in fluid systems
US7591279Aug 16, 2002Sep 22, 2009Cummins Filtration Ip Inc.Controlled release of additives in fluid systems
US7833953Aug 28, 2006Nov 16, 2010Afton Chemical CorporationLubricant composition
US7879775Jul 14, 2006Feb 1, 2011Afton Chemical CorporationLubricant compositions
US7883638May 27, 2008Feb 8, 2011Dober Chemical CorporationControlled release cooling additive compositions
US7902133Jul 14, 2006Mar 8, 2011Afton Chemical CorporationLubricant composition
US7938277May 27, 2008May 10, 2011Dober Chemical CorporationControlled release of microbiocides
US7947636Feb 27, 2004May 24, 2011Afton Chemical CorporationPower transmission fluids
US8109287Jul 22, 2009Feb 7, 2012Cummins Filtration Ip, Inc.Controlled release of additives in fluid systems
US8183314Jun 26, 2009May 22, 2012Exxonmobil Research And Engineering CompanyEmulsion compositions with a polymeric emulsifier
US8288326Sep 2, 2009Oct 16, 2012Chevron Oronite Company LlcNatural gas engine lubricating oil compositions
US8318643Jun 29, 2010Nov 27, 2012Cherron Oronite Technology B.V.Trunk piston engine lubricating oil compositions
US8425772Jul 29, 2011Apr 23, 2013Cummins Filtration Ip, Inc.Filtration device with releasable additive
US8426608Jan 21, 2011Apr 23, 2013Chevron Oronite Company LlcProcess for preparation of high molecular weight molybdenum succinimide complexes
US8465560Feb 1, 2010Jun 18, 2013Butamax Advanced Biofuels LlcGasoline deposit control additive composition
US8476460Jan 21, 2011Jul 2, 2013Chevron Oronite Company LlcProcess for preparation of low molecular weight molybdenum succinimide complexes
US8486877Nov 18, 2009Jul 16, 2013Chevron Oronite Company LlcAlkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals
US8546311Mar 10, 2009Oct 1, 2013Volkswagen AktiengesellsschaftMethod for lubricating a clutch-only automatic transmission component requiring lubrication
US8549897Jul 24, 2009Oct 8, 2013Chevron Oronite S.A.System and method for screening liquid compositions
US8557752Mar 22, 2006Oct 15, 2013Afton Chemical CorporationLubricating compositions
US8586520Jun 27, 2012Nov 19, 2013Exxonmobil Research And Engineering CompanyMethod of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
US8591747May 26, 2009Nov 26, 2013Dober Chemical Corp.Devices and methods for controlled release of additive compositions
US8632638Nov 15, 2011Jan 21, 2014Chevron Oronite Company LlcMethod for cleaning deposits from an engine fuel delivery system
US8633142Jul 29, 2009Jan 21, 2014Shell Oil CompanyPoly (hydroxycarboxylic acid) amide salt derivative and lubricating composition containing it
US8702968Apr 4, 2012Apr 22, 2014Chevron Oronite Technology B.V.Low viscosity marine cylinder lubricating oil compositions
US8702995May 27, 2008Apr 22, 2014Dober Chemical Corp.Controlled release of microbiocides
US8703666Jun 1, 2012Apr 22, 2014Exxonmobil Research And Engineering CompanyLubricant compositions and processes for preparing same
US8703669Feb 17, 2009Apr 22, 2014Afton Chemical CorporationUltra-low sulfur clutch-only transmission fluids
US8703680Nov 10, 2011Apr 22, 2014Chevron Oronite Company LlcLubricating composition containing friction modifier blend
US8709984Dec 15, 2009Apr 29, 2014Chevron Oronite Company LlcLubricating oil compositions
US8716202Dec 14, 2010May 6, 2014Chevron Oronite Company LlcMethod for improving fluorocarbon elastomer seal compatibility
US8796192Oct 29, 2010Aug 5, 2014Chevron Oronite Company LlcNatural gas engine lubricating oil compositions
US8841243Mar 31, 2010Sep 23, 2014Chevron Oronite Company LlcNatural gas engine lubricating oil compositions
US8933002Nov 10, 2011Jan 13, 2015Chevron Oronite Company LlcLubricating oil compositions
US8969265Mar 19, 2014Mar 3, 2015Chevron Oronite Company LlcLubricating oil compositions
US8969273Feb 18, 2009Mar 3, 2015Chevron Oronite Company LlcLubricating oil compositions
US9062269Mar 15, 2013Jun 23, 2015Exxonmobil Research And Engineering CompanyMethod for improving thermal-oxidative stability and elastomer compatibility
US9062271Oct 30, 2013Jun 23, 2015Chevron Oronite Technology B.V.Process for preparing an overbased salt of a sulfurized alkyl-substituted hydroxyaromatic composition
US9062273Aug 3, 2012Jun 23, 2015Chevron Oronite Company LlcLubricating oil compositions containing titanium complexes
US9068134Nov 28, 2012Jun 30, 2015Exxonmobil Research And Engineering CompanyMethod for improving engine wear and corrosion resistance
US9150472Dec 17, 2012Oct 6, 2015Shell Oil CompanyMethod and composition for inhibiting asphaltene deposition in a hydrocarbon mixture
US9150812Mar 8, 2013Oct 6, 2015Exxonmobil Research And Engineering CompanyAntioxidant combination and synthetic base oils containing the same
US9206374Dec 16, 2011Dec 8, 2015Chevron Oronite SasTrunk piston engine lubricating oil compositions
US9228149Jun 27, 2013Jan 5, 2016Exxonmobil Research And Engineering CompanyEnhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets
US9249091Dec 27, 2012Feb 2, 2016Chevron Oronite Company LlcPost-treated sulfurized salt of an alkyl-substituted hydroxyaromatic composition
US9267093May 21, 2010Feb 23, 2016Afton Chemical CorporationMethods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
US9315756Apr 4, 2013Apr 19, 2016Exxonmobil Research And Engineering CompanyBio-feeds based hybrid group V base stocks and method of production thereof
US9315761Sep 4, 2013Apr 19, 2016Exxonmobil Chemical Patents Inc.Lubricant and fuel dispersants and methods of preparation thereof
US9365794Feb 19, 2010Jun 14, 2016Infineum International LimitedWet friction clutch—lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
US9416307Dec 17, 2012Aug 16, 2016Shell Oil CompanyMethod and composition for inhibiting wax in a hydrocarbon mixture
US9422497Sep 4, 2013Aug 23, 2016Exxonmobil Research And Engineering CompanySynthetic lubricant basestocks and methods of preparation thereof
US9434906Mar 25, 2013Sep 6, 2016Chevron Oronite Company, LlcMarine diesel engine lubricating oil compositions
US9453173Dec 17, 2012Sep 27, 2016Shell Oil CompanyMethod and composition for inhibiting foam in a hydrocarbon mixture
US9487729Oct 22, 2013Nov 8, 2016Exxonmobil Chemical Patents Inc.Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives
US9493720Oct 20, 2014Nov 15, 2016Innospec LimitedGasoline composition, method and use
US9506007Nov 14, 2014Nov 29, 2016Chevron Oronite Technology B.V.Low sulfur marine distillate fuel trunk piston engine oil composition
US9506008Mar 19, 2014Nov 29, 2016Exxonmobil Research And Engineering CompanyMethod for improving engine fuel efficiency
US9506009May 29, 2014Nov 29, 2016Exxonmobil Research And Engineering CompanyLubricating oil compositions with engine wear protection
US9528071Feb 13, 2015Dec 27, 2016Chevron Oronite Technology B.V.Lubricating oil compositions with enhanced piston cleanliness
US9528074Feb 13, 2015Dec 27, 2016Chevron Oronite Technology B.V.Lubricating oil compositions with enhanced piston cleanliness
US9587231Aug 14, 2015Mar 7, 2017REG Life Sciences, LLCMethods and compositions related to thioesterase enzymes
US9708549Dec 18, 2013Jul 18, 2017Chevron Phillips Chemical Company LpMethod for making polyalphaolefins using aluminum halide catalyzed oligomerization of olefins
US9732300Jul 23, 2015Aug 15, 2017Chevron Phillipa Chemical Company LPLiquid propylene oligomers and methods of making same
US20020193650 *May 17, 2001Dec 19, 2002Goze Maria Caridad B.Low noack volatility poly alpha-olefins
US20030089026 *Feb 26, 2002May 15, 2003Jordan Frederick L.Method and composition for using organic, plant-derived, oil-extracted materials in resid fuel additives for reduced emissions
US20030089027 *Feb 26, 2002May 15, 2003Jordan Frederick L.Method and composition for using organic, plant-derived, oil-extracted materials in fossil fuels for reduced emissions
US20030089028 *Feb 26, 2002May 15, 2003Jordan Frederick L.Method and composition for using organic, plant-derived, oil-extracted materials in coal-based fuels for reduced emissions
US20030089029 *Feb 26, 2002May 15, 2003Jordan Frederick L.Method and composition for using organic, plant-derived, oil-extracted materials in two-cycle oil additives for reduced emissions
US20030089030 *Feb 26, 2002May 15, 2003Jordan Frederick L.Method and composition for using organic, plant-derived, oil-extracted materials in resid fuels for reduced emissions
US20030093943 *Feb 26, 2002May 22, 2003Jordan Frederick L.Method and composition for using organic, plant-derived, oil-extracted materials in diesel fuel additives for reduced emissions
US20030093944 *Feb 26, 2002May 22, 2003Jordan Frederick L.Method and composition for using organic, plant-derived, oil-extracted materials in two-cycle oils for reduced emissions
US20030093945 *Feb 26, 2002May 22, 2003Jordan Frederick L.Method and composition for using organic, plant-derived, oil-extracted materials in gasoline additives for reduced emissions
US20030097783 *Feb 26, 2002May 29, 2003Jordan Frederick L.Method and composition for using organic, plant-derived, oil-extracted materials in gasolines for reduced emissions
US20030122104 *Feb 12, 2003Jul 3, 2003Dober Chemical CorporationLiquid replacement systems
US20030167679 *Jun 12, 2002Sep 11, 2003Jordan Frederick L.Organic cetane improver
US20040033908 *Aug 16, 2002Feb 19, 2004Deckman Douglas E.Functional fluid lubricant using low Noack volatility base stock fluids
US20040091654 *Nov 3, 2003May 13, 2004Fleetguard, Inc.Controlled release of additives in cooling systems
US20050019236 *Aug 16, 2002Jan 27, 2005Harold MartinControlled release of additives in fluid systems
US20050045527 *Oct 6, 2004Mar 3, 2005Goze Maria Caridad B.Low noack volatility poly alpha-olefins
US20050065043 *Sep 23, 2003Mar 24, 2005Henly Timothy J.Power transmission fluids having extended durability
US20050065044 *May 8, 2001Mar 24, 2005Migdal Cyril ANanosized particles of molybdenum sulfide and derivatives,method for its preparation and uses thereof as lubricant additive
US20050070446 *Sep 25, 2003Mar 31, 2005Ethyl Petroleum Additives, Inc.Boron free automotive gear oil
US20050101494 *Nov 10, 2003May 12, 2005Iyer Ramnath N.Lubricant compositions for power transmitting fluids
US20050192185 *Feb 27, 2004Sep 1, 2005Saathoff Lee D.Power transmission fluids
US20050202979 *Mar 9, 2005Sep 15, 2005Ethyl Petroleum Additives, Inc.Power transmission fluids with enhanced extreme pressure characteristics
US20050250656 *May 4, 2004Nov 10, 2005Masahiro IshikawaContinuously variable transmission fluid
US20050268531 *Jun 2, 2004Dec 8, 2005Polar Molecular CorporationMotor fuel additive composition
US20050268532 *Jun 2, 2004Dec 8, 2005Polar Molecular CorporationMotor fuel additive composition
US20050268533 *Jun 2, 2004Dec 8, 2005Polar Molecular CorporationMotor fuel additive composition
US20050268534 *Jun 2, 2004Dec 8, 2005Polar Molecular CorporationMotor fuel additive composition
US20050268537 *Jun 2, 2004Dec 8, 2005Polar Molecular CorporationMotor fuel additive composition
US20060003905 *Jul 2, 2004Jan 5, 2006Devlin Cathy CAdditives and lubricant formulations for improved corrosion protection
US20060025314 *Oct 11, 2004Feb 2, 2006Afton Chemical CorporationPower transmission fluids with enhanced extreme pressure and antiwear characteristics
US20060049080 *Jun 25, 2004Mar 9, 2006Chevron U.S.A. Inc.Thermally stable blends of highly paraffinic distillate fuel component with conventional distillate fuel component
US20060196111 *Mar 4, 2005Sep 7, 2006Colucci William JFuel additive composition
US20060201056 *Jan 27, 2006Sep 14, 2006Oryxe Energy International, Inc.Biodiesel fuel additive
US20060217273 *Mar 22, 2006Sep 28, 2006Nubar OzbalikLubricating compositions
US20060223716 *Apr 4, 2005Oct 5, 2006Milner Jeffrey LTractor fluids
US20060264339 *May 19, 2005Nov 23, 2006Devlin Mark TPower transmission fluids with enhanced lifetime characteristics
US20070000831 *Sep 5, 2006Jan 4, 2007Fleetguard, Inc.Controlled release of additives in cooling systems
US20070054813 *Oct 25, 2006Mar 8, 2007Chip HewetteBoron free automotive gear oil
US20070111906 *Nov 12, 2005May 17, 2007Milner Jeffrey LRelatively low viscosity transmission fluids
US20070241042 *Jun 5, 2007Oct 18, 2007Dober Chemical CorporationControlled release of additives in fluid systems
US20070259792 *Mar 20, 2007Nov 8, 2007Null Volker KFunctional fluid compositions
US20070270317 *Apr 25, 2007Nov 22, 2007Milner Jeffrey LPower Transmission Fluids
US20070278133 *Sep 13, 2004Dec 6, 2007Gregory HemighausThermally stable jet prepared from highly paraffinic distillate fuel component and conventional distillate fuel component
US20080009426 *Aug 15, 2007Jan 10, 2008Iyer Ramnath NLubricant Compositions and Methods Comprising Dispersant and Detergent
US20080015125 *Jul 14, 2006Jan 17, 2008Devlin Mark TLubricant compositions
US20080015127 *Jul 14, 2006Jan 17, 2008Loper John TBoundary friction reducing lubricating composition
US20080026973 *May 2, 2007Jan 31, 2008Nelson David CLubricating oil composition
US20080051305 *Aug 28, 2006Feb 28, 2008Devlin Mark TLubricant composition
US20080064616 *Oct 14, 2005Mar 13, 2008Huntsman Petrochemical CorporationFuel And Oil Detergents
US20080119377 *Nov 22, 2006May 22, 2008Devlin Mark TLubricant compositions
US20080296234 *May 27, 2008Dec 4, 2008Dober Chemical CorporationControlled release of microbiocides
US20090011963 *Jul 6, 2007Jan 8, 2009Afton Chemical CorporationTruck fleet fuel economy by the use of optimized engine oil, transmission fluid, and gear oil
US20090042752 *Aug 9, 2007Feb 12, 2009Malcolm WaddoupsLubricant Compositions with Reduced Phosphorous Content for Engines having Catalytic Converters
US20090156445 *Dec 13, 2007Jun 18, 2009Lam William YLubricant composition suitable for engines fueled by alternate fuels
US20090158642 *Mar 5, 2009Jun 25, 2009Polar Molecular CorporationMotor fuel additive composition
US20090158643 *Mar 5, 2009Jun 25, 2009Polar Molecular CorporationMotor fuel additive composition
US20090233822 *Feb 17, 2009Sep 17, 2009Afton Chemical CorporationUltra-low sulfur clutch-only transmission fluids
US20090233823 *Mar 10, 2009Sep 17, 2009Volkswagen AktiengesellschaftMethod for lubricating a clutch-only automatic transmission component requiring lubrication
US20090283466 *Jul 22, 2009Nov 19, 2009Cummins Filtration Ip Inc.Controlled release of additives in fluid systems
US20090294345 *May 27, 2008Dec 3, 2009Dober Chemical CorporationControlled release of microbiocides
US20090304868 *May 26, 2009Dec 10, 2009Dober Chemical CorporationControlled release cooling additive composition
US20100004382 *Jun 26, 2009Jan 7, 2010Exxonmobil Research And Engineering CompanyEmulsion compositions with a polymeric emulsifier
US20100024286 *Jul 29, 2009Feb 4, 2010Smith Susan JaneLiquid fuel compositions
US20100024287 *Jul 29, 2009Feb 4, 2010Smith Susan JaneLiquid fuel compositions
US20100206260 *Feb 18, 2009Aug 19, 2010Chevron Oronite Company LlcMethod for preventing exhaust valve seat recession
US20100279901 *May 21, 2010Nov 4, 2010Iyer Ramnath NMethods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
US20110010985 *Sep 21, 2010Jan 20, 2011Peter Wangqi HouFuel Additive to Control Deposit Formation
US20110016954 *Jul 24, 2009Jan 27, 2011Chevron Oronite S.A.System and method for screening liquid compositions
US20110053814 *Sep 2, 2009Mar 3, 2011Chevron Oronite Company LlcNatural gas engine lubricating oil compositions
US20110118160 *Nov 18, 2009May 19, 2011Chevron Oronite Company LlcAlkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals
US20110143979 *Dec 15, 2009Jun 16, 2011Chevron Oronite Company LlcLubricating oil compositions
US20110207640 *Jul 29, 2009Aug 25, 2011Jan Elsa Eugenia CartyPoly (hydroxycarboxylic acid) amide salt derivative and lubricating composition containing it
US20120260876 *Jun 1, 2010Oct 18, 2012Innospec LimitedMethod of increasing fuel efficiency
DE2040270A1 *Aug 13, 1970Nov 4, 1971Chevron ResVerfahren zur Herstellung Polyolefin-substituierter Amine
DE2125039A1 *May 19, 1971Dec 2, 1971Shell Int ResearchTitle not available
DE2245918A1 *Sep 19, 1972Mar 22, 1973Shell Int ResearchVerfahren zur herstellung von aminen und deren verwendung als zusatz zu schmiermitteln und kraftstoffen
DE2555920A1 *Dec 12, 1975Jul 8, 1976Rohm & HaasMehrzweckzusatz fuer fluessige kraftstoffe
DE2555922A1 *Dec 12, 1975Jul 8, 1976Rohm & HaasMehrzweckzusatzmischung fuer fluessige kraftstoffe
DE2727502A1 *Jun 18, 1977Jan 12, 1978Chevron ResKraftstoffgemisch mit additiven gegen rueckstandsbildung
DE102009001301A1Mar 3, 2009Sep 24, 2009Audi AgVerfahren zum Schmieren einer Komponente nur für die Kupplung eines automatischen Getriebes, welche Schmierung erfordert
DE102009012567A1Mar 11, 2009Oct 1, 2009Afton Chemical Corp.Clutch-only transmission fluid useful for lubrication comprises oil formulated with additive components having metal detergent, phosphorus-based wear preventative, phosphorylated and boronated dispersant, sulfurized extreme pressure agent
EP0277345A1 *Dec 22, 1987Aug 10, 1988BASF AktiengesellschaftFuel or lubricant composition containing polybutyl or polyisobutyl derivatives
EP0327097A1 *Feb 3, 1989Aug 9, 1989Texaco Development CorporationORI-inhibited motor fuel composition and storage stable concentrate
EP0460957A2 *Jun 6, 1991Dec 11, 1991Tonen CorporationGasoline additive composition
EP0460957A3 *Jun 6, 1991May 6, 1992Tonen CorporationGasoline additive composition
EP0558835A1Jan 30, 1992Sep 8, 1993Albemarle CorporationBiodegradable lubricants and functional fluids
EP0639589A1 *Jul 21, 1994Feb 22, 1995Ferro CorporationProcess for the production of fuel additives from chlorinated polybutenes
EP0654524A2 *Jun 6, 1991May 24, 1995Tonen CorporationGasoline additive composition
EP0654524A3 *Jun 6, 1991Oct 11, 1995Tonen CorpGasoline additive composition.
EP0683220A2May 18, 1995Nov 22, 1995Ethyl CorporationLubricant additive compositions
EP0695798A2Aug 2, 1995Feb 7, 1996The Lubrizol CorporationLubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound
EP0695799A2Jul 28, 1995Feb 7, 1996The Lubrizol CorporationCombination of a sulfer compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
EP0713908A1Nov 21, 1995May 29, 1996Ethyl CorporationPower transmission fluids
EP0769546A2Oct 17, 1996Apr 23, 1997The Lubrizol CorporationAntiwear enhancing composition for lubricants and functional fluids
EP1013745A1 *Nov 8, 1999Jun 28, 2000Chevron Chemical Company LLCFuel additive compositions containing aromatic esters of polyalkylphenoxyalkanols and aliphatic amines
EP1331376A2Jan 22, 2003Jul 30, 2003Chevron Oronite Company LLCMethod for removing engine deposits in a reciprocating internal combustion engine
EP1568759A2Feb 24, 2005Aug 31, 2005Afton Chemical CorporationPower transmission fluids
EP1640440A1Aug 30, 2005Mar 29, 2006Infineum International LimitedFriction and/or wear reduction in manual or automated manual transmissions
EP1930401A1Nov 21, 2007Jun 11, 2008Chevron Oronite Company LLCFunctional fluids comprising alkyl toluene sulfonates
EP1942177A2Dec 19, 2007Jul 9, 2008Chevron Oronite Company LLCLubricating oil providing enhanced piston cleanliness
EP1947164A1Dec 19, 2007Jul 23, 2008Chevron Oronite Technology B.V.Engine lubricant with enhanced thermal stability
EP2000523A1Mar 26, 2008Dec 10, 2008Chevron Oronite S.A.Lubricating oil with enhanced protection against wear and corrosion
EP2031045A1Jul 29, 2008Mar 4, 2009Infineum International LimitedLubricant compositions with reduced phosphorous content for engines having catalytic converters
EP2042582A2Aug 25, 2008Apr 1, 2009Afton Chemical CorporationSurface passivation and to methods for the reduction of fuel thermal degradation deposits
EP2072611A1Nov 11, 2008Jun 24, 2009Afton Chemical CorporationLubricant composition suitable for engines fueled by alternate fuels
EP2077316A2Dec 4, 2008Jul 8, 2009Infineum International LimitedLubricant compositions with low HTHS for a given SAE viscosity grade
EP2230292A1Nov 8, 2004Sep 22, 2010Afton Chemical CorporationMethods of lubricating transmissions
EP2272940A1Sep 13, 2002Jan 12, 2011Afton Chemical Intangibles LLCFuels compositions for direct injection gasoline engines
EP2278327A1Jul 23, 2010Jan 26, 2011Chevron Oronite S.A.System and Method for Screening Liquid Compositions
EP2302020A1Jul 25, 2008Mar 30, 2011Innospec LimitedUse of additives for improving oxidation stability of a fuel oil composition
EP2302023A2Oct 2, 2003Mar 30, 2011R.T. Vanderbilt Company, Inc.Synergistic organoborate compositions and lubricating compositions containing same
EP2366762A1Oct 2, 2003Sep 21, 2011R.T. Vanderbilt Company Inc.Synergistic organoborate compositions and lubricating compositions containing same
EP2371933A1Feb 1, 2007Oct 5, 2011The Lubrizol CorporationTartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof
EP2402421A2Jun 22, 2011Jan 4, 2012Chevron Oronite Technology B.V.Trunk Piston Engine Lubricating Oil Compositions
EP2436753A1Oct 2, 2003Apr 4, 2012R.T. Vanderbilt Company Inc.Synergistic organoborate compositions and lubricating compositions containing same
EP2455406A1Nov 6, 2007May 23, 2012The Lubrizol CorporationQuaternary Ammonium Salt of a Polyalkene-Substituted Amine Compound
EP2460870A1Oct 2, 2003Jun 6, 2012R.T. Vanderbilt Company, Inc.Synergistic organoborate compositions and lubricating compositions containing same
EP2604676A1Dec 17, 2012Jun 19, 2013Chevron Oronite Technology B.V.Trunk piston engine lubricating oil compositions
EP2910630A1Sep 23, 2010Aug 26, 2015REG Life Sciences, LLCProduction of fatty acid derivatives
EP2913387A1Sep 1, 2010Sep 2, 2015Chevron Oronite Company LLCNatural gas engine lubricating oil compositions
EP3020790A1Nov 11, 2015May 18, 2016Chevron Oronite Technology B.V.Trunk piston engine oil composition for low sulfur marine distillate fueled engines
EP3070153A1Aug 30, 2011Sep 21, 2016The Lubrizol CorporationHydroxychroman derivatives as antioxidants
EP3205705A1Jun 6, 2014Aug 16, 2017Basf SeAlkylene oxide and hydrocarbyl-substituted polycarboxylic acid quaternised alkylamine as additives in fuels and lubricants and their use
WO1990010051A1 *Feb 20, 1990Sep 7, 1990Union Oil Company Of CaliforniaFuel composition for control of intake valve deposits
WO1991003529A1 *Sep 8, 1989Mar 21, 1991Chevron Research CompanySynergistic fuel compositions
WO1991012302A1 *Feb 7, 1991Aug 22, 1991Exxon Chemical Patents Inc.Gasoline fuel for internal combustion engines
WO1991013949A1 *Mar 5, 1991Sep 19, 1991Polar Molecular CorporationMotor fuel additive composition and method for preparation thereof
WO1992021736A1May 26, 1992Dec 10, 1992The Lubrizol CorporationTwo-cycle lubricant and method of using same
WO1994014706A1 *Dec 20, 1993Jul 7, 1994Chevron Research And Technology CompanyFuel additive compositions containing poly(oxyalkylene) hydroxyaromatic ethers and aliphatic amines
WO1994014928A1 *Dec 20, 1993Jul 7, 1994Chevron Research And Technology CompanyFuel additive compositions containing poly(oxyalkylene) hydroxyaromatic esters and aliphatic amines
WO1994014929A1 *Dec 20, 1993Jul 7, 1994Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc.Fuel additive compositions containing aliphatic amines and polyalkyl hydroxyaromatics
WO1995029974A1 *Apr 24, 1995Nov 9, 1995Chevron Chemical CompanyFuel additive compositions containing an aliphatic amine, a polyolefin and a poly(oxyalkylene) monool
WO1998012284A1 *Sep 17, 1997Mar 26, 1998Petrokleen, Ltd.Method of synthesizing pure additives and the improved compositions thereby produced
WO1998047989A1Mar 19, 1998Oct 29, 1998Exxon Chemical Patents Inc.Power transmission fluids containing alkyl phosphonates
WO2002010276A2Jul 30, 2001Feb 7, 2002The Lubrizol CorporationPolymeric mixture useful as viscosity improver for lubricating oils
WO2006094011A2Feb 28, 2006Sep 8, 2006R.T. Vanderbilt Company, Inc.Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
WO2007037642A1 *Sep 29, 2006Apr 5, 2007Hae Dong Chemical Co., Ltd.Process for the modified polymers by the modification of chlorine containing polymers
WO2008013698A1Jul 17, 2007Jan 31, 2008Exxonmobil Research And Engineering CompanyMethod for lubricating heavy duty geared apparatus
WO2008060888A2Nov 6, 2007May 22, 2008The Lubrizol CorporationQuaternary ammonium salt of a polyalkene-substituted amine compound
WO2009074606A1 *Dec 10, 2008Jun 18, 2009Basf SeHydrocarbylphenols as intake valve clean-up boosters
WO2009119831A1Mar 27, 2009Oct 1, 2009Fujifilm CorporationComposition and method for forming coating film
WO2010005947A2Jul 7, 2009Jan 14, 2010Innospec Fuel Specialties, LLCFuel composition with enhanced low temperature properties
WO2010075483A2Dec 23, 2009Jul 1, 2010Ls9, Inc.Methods and compositions related to thioesterase enzymes
WO2010091069A1Feb 3, 2010Aug 12, 2010Butamax™ Advanced Biofuels LLCGasoline deposit control additive compositions
WO2010096325A1Feb 11, 2010Aug 26, 2010The Lubrizol CorporationAmine derivatives as friction modifiers in lubricants
WO2010096472A2Feb 17, 2010Aug 26, 2010Chevron Oronite Company LlcMethod for preventing exhaust valve seat recession
WO2010136822A2Jun 1, 2010Dec 2, 2010Innospec LimitedMethod and use
WO2010139994A1Jun 1, 2010Dec 9, 2010Innospec LimitedImprovements in efficiency
WO2010147993A1Jun 15, 2010Dec 23, 2010Chevron Phillips Chemical Company LpOligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends
WO2010149712A1Jun 23, 2010Dec 29, 2010Shell Internationale Research Maatschappij B.V.Lubricating composition
WO2011026990A1Sep 7, 2010Mar 10, 2011Shell Internationale Research Maatschappij B.V.Lubricating compositions
WO2011102835A1Feb 19, 2010Aug 25, 2011Toyota Jidosha Kabushiki KaishaWet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents
WO2011102836A1Feb 19, 2010Aug 25, 2011Infineum International LimitedWet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
WO2011141731A1May 10, 2011Nov 17, 2011Innospec LimitedComposition, method and use
WO2011143051A1May 6, 2011Nov 17, 2011The Lubrizol CorporationTartaric acid derivatives in hths fluids
WO2011143418A1May 12, 2011Nov 17, 2011Exxonmobil Research And Engineering CompanyMethod for reducing one or more of deposits and friction of a lubricating oil
WO2012033668A1Aug 30, 2011Mar 15, 2012The Lubrizol CorporationHydroxychroman derivatives as engine oil antioxidants
WO2012051075A2Oct 7, 2011Apr 19, 2012Chevron Oronite Company LlcLubricating composition containing multifunctional borated hydroxylated amine salt of a hindered phenolic acid
WO2012076896A1Dec 8, 2011Jun 14, 2012Innospec LimitedImprovements in or relating to additives for fuels and lubricants
WO2012084906A1Dec 20, 2011Jun 28, 2012Rhodia OperationsFuel additive composition containing a dispersion of iron particles and a detergent
WO2012099734A2Jan 9, 2012Jul 26, 2012Chevron Oronite Company LlcImproved process for preparation of low molecular weight molybdenum succinimide complexes
WO2012099736A2Jan 9, 2012Jul 26, 2012Chevron Oronite Company LlcImproved process for preparation of high molecular weight molybdenum succinimide complexes
WO2012141855A1Mar 21, 2012Oct 18, 2012R.T. Vanderbilt Company, Inc.Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
WO2012163935A2May 30, 2012Dec 6, 2012Shell Internationale Research Maatschappij B.V.Liquid fuel compositions
WO2013003392A1Jun 27, 2012Jan 3, 2013Exxonmobil Research And Engineering CompanyMethod of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
WO2013003394A1Jun 27, 2012Jan 3, 2013Exxonmobil Research And Engineering CompanyLubricating compositions containing polyetheramines
WO2013003405A1Jun 27, 2012Jan 3, 2013Exxonmobil Research And Engineering CompanyLubricating compositions containing polyalkylene glycol mono ethers
WO2013003406A1Jun 27, 2012Jan 3, 2013Exxonmobil Research And Engineering CompanyLow viscosity engine oil with superior engine wear protection
WO2013012987A1Jul 19, 2012Jan 24, 2013The Lubrizol CorporationOverbased friction modifiers and methods of use thereof
WO2013013026A1Jul 19, 2012Jan 24, 2013The Lubrizol CorporationCarboxylic pyrrolidinones and methods of use thereof
WO2013043332A1Aug 29, 2012Mar 28, 2013The Lubrizol CorporationQuaternary ammonium salts in heating oils
WO2013055480A1Sep 12, 2012Apr 18, 2013Exxonmobil Research And Engineering CompanyLow viscosity engine oil compositions
WO2013055481A1Sep 12, 2012Apr 18, 2013Exxonmobil Research And Engineering CompanyHigh efficiency engine oil compositions
WO2013055482A1Sep 12, 2012Apr 18, 2013Exxonmobil Research And Engineering CompanyLubricating compositions
WO2013066915A1Oct 31, 2012May 10, 2013Exxonmobil Research And Engineering CompanyLubricants with improved low-temperature fuel economy
WO2013070376A2Oct 11, 2012May 16, 2013Vanderbilt Chemicals, LlcLubricant composition
WO2013074498A1Nov 13, 2012May 23, 2013Exxonmobil Research And Engineering CompanyMethod for improving engine fuel efficiency
WO2013082206A1Nov 29, 2012Jun 6, 2013Exxonmobil Research And Engineering CompanyMethod for improving engine wear and corrosion resistance
WO2013096532A1Dec 20, 2012Jun 27, 2013Exxonmobil Research And Engineering CompanyMethod for improving engine fuel efficiency
WO2013101256A2Dec 28, 2012Jul 4, 2013Butamax (Tm) Advanced Biofuels LlcCorrosion inhibitor compositions for oxygenated gasolines
WO2013142110A1Mar 11, 2013Sep 26, 2013Exxonmobil Research And Engineering CompanyNovel antioxidant combination and synthetic base oils containing the same
WO2013151911A1Apr 1, 2013Oct 10, 2013The Lubrizol CorporationBearing lubricants for pulverizing equipment
WO2013165792A1Apr 25, 2013Nov 7, 2013Lubrizol Advanced Materials, Inc.Aromatic dispersant composition
WO2013181318A1May 30, 2013Dec 5, 2013Exxonmobil Research And Engineering CompanyLubricant compostions and processes for preparing same
WO2014008121A1Jun 28, 2013Jan 9, 2014Exxonmobil Research And Engineering CompanyEnhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets
WO2014047180A1Sep 18, 2013Mar 27, 2014Exxonmobil Research And Engineering CompanyLubricant and fuel dispersants and methods of preparation thereof
WO2014047184A1Sep 18, 2013Mar 27, 2014Exxonmobil Research And Engineering CompanyLubricant and fuel dispersants and methods of preparation thereof
WO2014065984A1Sep 27, 2013May 1, 2014Exxonmobil Reearch And Engineering CompanyHigh viscosity index lubricating oil base stock viscosity modifier combinations, and lubricating oils derived therefrom
WO2014066344A1Oct 22, 2013May 1, 2014The Lubrizol CorporationDiesel detergent without a low molecular weight penalty
WO2014066444A1Oct 23, 2013May 1, 2014Exxonmobil Research And Engineering ComapnyFunctionalized polymers and oligomers as corrosion inhibitors and antiwear additives
WO2014088814A1Nov 21, 2013Jun 12, 2014The Lubrizol CorporationPyran dispersants
WO2014107314A1Dec 19, 2013Jul 10, 2014Exxonmobil Research And Engineering CompanyLubricating compositions having improved shear stability
WO2014107315A1Dec 19, 2013Jul 10, 2014Exxonmobil Research And Engineering CompanyMethod for improving engine fuel efficiency
WO2014149406A1Feb 25, 2014Sep 25, 2014Exxonmobil Research And Engineering CompanyMethod for improving thermal -oxidative stability and elastomer compatibility
WO2014158533A1Feb 24, 2014Oct 2, 2014Exxonmobil Research And Engineering CompanyLubricating composition providing high wear resistance
WO2014158602A1Feb 26, 2014Oct 2, 2014Exxonmobil Research And Engineering CompanyMethod for improving emulsion characteristics of engine oils
WO2014193692A1May 20, 2014Dec 4, 2014The Lubrizol CorporationAsphaltene inhibition
WO2015031043A1Aug 12, 2014Mar 5, 2015Lubrizol Advanced Materials, Inc.Non-fused aromatic dispersant composition
WO2015050690A1Sep 15, 2014Apr 9, 2015Exxonmobil Research And Engineering CompanyCompositions with improved varnish control properties
WO2015095336A1Dec 17, 2014Jun 25, 2015Chevron Phillips Chemical Company LpMethod for making polyolefins using aluminum halide catalyzed oligomerization of olefins
WO2015099819A1Apr 1, 2014Jul 2, 2015Exxonmobil Research And Engineering CompanyMethod for improving engine fuel efficiency
WO2015099820A1Apr 1, 2014Jul 2, 2015Exxonmobil Research And Engineering CompanyMethod for improving engine fuel efficiency
WO2015099821A1Apr 1, 2014Jul 2, 2015Exxonmobil Research And Engineering CompanyMethod for improving engine fuel efficiency
WO2015099907A1Nov 19, 2014Jul 2, 2015Exxonmobil Research And Engineering CompanyLow viscosity ester lubricant and method for using
WO2015113681A1Dec 4, 2014Aug 6, 2015Basf SePolycarboxylic-acid-based additives for fuels and lubricants
WO2015157071A1Apr 2, 2015Oct 15, 2015Lubrizol Advanced Materials, Inc.Ink jet ink compositions
WO2015171292A1Apr 20, 2015Nov 12, 2015Exxonmobil Research And Engineering CompanyMethod for preventing or reducing engine knock and pre-ignition
WO2015171978A1May 8, 2015Nov 12, 2015Exxonmobil Research And Engineering CompanyMethod for preventing or reducing low speed pre-ignition
WO2015171980A1May 8, 2015Nov 12, 2015Exxonmobil Research And Engineering CompanyMethod for preventing or reducing low speed pre-ignition
WO2015171981A1May 8, 2015Nov 12, 2015Exxonmobil Research And Engineering CompanyMethod for preventing or reducing low speed pre-ignition
WO2015183455A1Apr 29, 2015Dec 3, 2015Exxonmobil Research And Engineering CompanyLubricating oil compositions with engine wear protection
WO2015200592A1Jun 25, 2015Dec 30, 2015The Lubrizol CorporationMixtures of friction modifiers to provide good friction performance to transmission fluids
WO2016043944A1Aug 27, 2015Mar 24, 2016Exxonmobil Research And Engineering CompanyComposition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2016073149A1Oct 13, 2015May 12, 2016Exxonmobil Research And Engineering CompanyLow transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
WO2016106211A1Dec 21, 2015Jun 30, 2016Exxonmobil Research And Engineering CompanyMethods for authentication and identification of petroleum products
WO2016106214A1Dec 21, 2015Jun 30, 2016Exxonmobil Research And Engineering CompanyMethods for determining condition and quality of petroleum products
WO2016109322A1Dec 22, 2015Jul 7, 2016Exxonmobil Research And Engineering CompanyLubricating oil compositions containing encapsulated microscale particles
WO2016109325A1Dec 22, 2015Jul 7, 2016Exxonmobil Research And Engineering CompanyLubricating oil compositions containing encapsulated microscale particles
WO2016109376A1Dec 28, 2015Jul 7, 2016Exxonmobil Research And Engineering CompanyLubricating oil compositions with engine wear protection
WO2016109382A1Dec 28, 2015Jul 7, 2016Exxonmobil Research And Engineering CompanyLubricating oil compositions with engine wear protection
WO2016144639A1Mar 2, 2016Sep 15, 2016The Lubrizol CorporationLubricating compositions comprising an anti-wear/friction modifying agent
WO2016191409A1May 24, 2016Dec 1, 2016Exxonmobil Research And Engineering CompanyComposition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2016200606A1May 25, 2016Dec 15, 2016Exxonmobil Research And Engineering CompanyInverse micellar compositions containing lubricant additives
WO2017007670A1Jun 30, 2016Jan 12, 2017Exxonmobil Research And Engineering CompanyComposition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2017117178A1Dec 28, 2016Jul 6, 2017Exxonmobil Research And Engineering CompanyBright stock production from deasphalted oil
WO2017142805A1Feb 10, 2017Aug 24, 20173M Innovative Properties CompanyPolishing systems and methods of making and using same