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Patent US6211122 - Carboxylic compositions and derivatives thereof and use as lubricating oil ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsA carboxylic composition comprising hydrocarbon substituted carboxylic acylating agents prepared by reacting a polyolefin and a terpolymer, simultaneously or individually in any order, with at least one carboxylic reactant selected from the group consisting of compounds of the formula R3C(O)(R4)nC(O)OR5...http://www.google.com/patents/US6211122?utm_source=gb-gplus-sharePatent US6211122 - Carboxylic compositions and derivatives thereof and use as lubricating oil and fuel additivesAdvanced Patent SearchPublication numberUS6211122 B1Publication typeGrantApplication numberUS 09/122,949Publication dateApr 3, 2001Filing dateJul 27, 1998Priority dateJul 27, 1998Fee statusLapsedAlso published asCA2278275A1, EP0976812A1Publication number09122949, 122949, US 6211122 B1, US 6211122B1, US-B1-6211122, US6211122 B1, US6211122B1InventorsJohn K. Pudelski, Jeffry G. Dietz, Matthew R. SivikOriginal AssigneeThe Lubrizol CorporationExport CitationBiBTeX, EndNote, RefManPatent Citations (19), Referenced by (1), Classifications (54), Legal Events (5) External Links: USPTO, USPTO Assignment, EspacenetCarboxylic compositions and derivatives thereof and use as lubricating oil and fuel additives
US 6211122 B1Abstract
What is claimed is: 1. A carboxylic composition comprising hydrocarbon substituted carboxylic acylating agents prepared by reacting a polyolefin and a terpolymer, simultaneously or individually in any order, with at least one carboxylic reactant selected from the group consisting of compounds of the formula
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof having the general formula wherein each of R3 and R5 and each R9 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1.
16. The composition of claim 1 wherein the at least one carboxylic reactant (IV) or reactive source thereof is a compound of the formula wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, R9 is hydrocarbyl and n is 0 or 1.
(A) a polyolefin substituted carboxylic acylating agent; and (B) a terpolymer substituted carboxylic acylating agent; wherein (A) is prepared by reacting at least one polyolefin, and (B) is prepared by reacting at least one terpolymer; each individually with at least one carboxylic reactant selected from the group consisting of compounds of the formula R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof having the general formula wherein each of R3 and R5 and each R9 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1.
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof having the general formula wherein each of R3 and R5 and each R9 is independently H or a hydrocarbyl group. R4 is a divalent hydrocarbylene group, and n is 0 or 1.
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof having the general formula wherein each of R3 and R5 and each R9 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, then adding to the reaction mixture at least one terpolymer and optionally additional carboxylic reactant then reacting the mixture.
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof having the general formula wherein each of R3 and R5 and each R9 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, with at least one reactant selected from the group consisting of (1) an amine characterized by the presence within its structure of at least one HN<group; (2) an alcohol; (3) a reactive metal or a reactive metal compound; and (4) a mixture of 2 or more of (1) through (3); the components of (4) being reacted with each carboxylic acylating agent simultaneously or sequentially, in any order.
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof having the general formula wherein each of R3 and R5 and each R9 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1 with at least one reactant selected from the group consisting of (1) an amine characterized by the presence within its structure of at least one HN<group; (2) an alcohol; (3) a reactive metal or a reactive metal compound; and (4) a mixture of 2 or more of (1) through (3); the components of (4) being reacted with each carboxylic acylating agent simultaneously or sequentially, in any order.
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof having the general formula wherein each of R3 and R5 and each R9 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, with at least one reactant selected from the group consisting of (1) an amine characterized by the presence within its structure of at least one HN<group; (2) an alcohol; (3) a reactive metal or a reactive metal compound; and (4) a mixture of 2 or more of (1) through (3); the components of (4) being reacted with each carboxylic acylating agent simultaneously or sequentially, in any order, then combining the products obtained thereby.
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof having the general formula wherein each of R3 and R5 and each R9 is independently H or a hydrocarbyl group, R is a divalent hydrocarbylene group, and n is 0 or 1, then adding to the reaction mixture at least one terpolymer and optionally additional carboxylic reactant, then reacting the mixture, with at least one reactant selected from the group consisting of (1) an amine characterized by the presence within its structure of at least one HN<group; (2) an alcohol; (3) a reactive metal or a reactive metal compound; and (4) a mixture of 2 or more of (1) through (3); the components of (4) being reacted with the carboxylic acylating agent simultaneously or sequentially, in any order.
Conventional dispersants are poor contributors to improving high temperature, e.g., 100� C., viscosity. Mixtures of conventional dispersants with polymeric viscosity improvers are often used but such combinations are costly and may adversely affect low temperature viscometric performance.
It has now been found that mixtures of carboxylic compositions and derivatives thereof, as set forth in greater detail hereinbelow provide improved 100� C. viscosity to lubricants without adversely affecting low temperature properties.
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R and R is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof.
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof.
In one embodiment, the monoolefinic groups are predominantly vinylidene groups, e.g., groups of the formula especially those of the formula although the polybutenes may also comprise other olefinic configurations.
In one embodiment the polybutene is substantially monoolefinic, comprising at least about 30 mole %, preferably at least about 50 mole % vinylidene groups, more often at least about 70 mole % vinylidene groups. Such materials and methods for preparing them are described in U.S. Pat. Nos. 5,286,823 and 5,408,018, which are expressly incorporated herein by reference. They are commercially available, for example under the tradenames ULTRAVIS� (BP Chemicals) and GLISSOPAL� (BASF).
R3C(O)(R4)nC(O)OR5 (IV) wherein each of R3 and R5 is independently H or a hydrocarbyl group, preferably H or lower alkyl, R4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof. Most preferably R3 is H.
In another embodiment, the monoamine may be a hydroxyamine. Typically, the hydroxyamines are primary or secondary alkanolamines or mixtures thereof. As stated above, tertiary monoamines do not possess an N—H group; however, tertiary alkanol monoamines sometimes can react to form a tertiary amino group containing ester. Alkanol amines that possess an N—H group can be represented, for example, by the formulae: wherein each R4 is independently a hydrocarbyl group of one to about 22 carbon atoms or hydroxyhydrocarbyl group of two to about 22 carbon atoms, preferably one to about four, and R′ is a divalent hydrocarbyl group of about two to about 18 carbon atoms, preferably two to about four. The group —R′—OH in such formulae represents the hydroxyhydrocarbyl group. R′ can be an acyclic, alicyclic or aromatic group. Typically, R′ is an acyclic straight or branched alkylene group such as an ethylene, 1,2-propylene, 1,2-butylene, 1,2-octadecylene, etc. group. When two R4 groups are present in the same molecule they can be joined by a direct carbon-to-carbon bond or through a heteroatom (e.g., oxygen, nitrogen or sulfur) to form a 5-, 6-, 7- or 8-membered ring structure. Examples of such heterocyclic amines include N-(hydroxyl lower alkyl)-morpholines, -thiomorpholines, -piperidines, -oxazolidines, -thiazolidines and the like. Typically, however, each R4 is independently a methyl, ethyl, propyl, butyl, pentyl or hexyl group.
Other useful types of polyamine mixtures are those resulting from stripping of the above-described polyamine mixtures to leave as residue what is often termed “polyamine bottoms”. In general, alkylene polyamine bottoms can be characterized as having less than two, usually less than 1% (by weight) material boiling below about 200� C. A typical sample of such ethylene polyamine bottoms obtained from the Dow Chemical Company of Freeport, Texas, designated “E-100” has a specific gravity at 15.6� C. of 1.0168, a percent nitrogen by weight of 33.15 and a viscosity at 40� C. of 121 centistokes. Gas chromatography analysis of such a sample contains about 0.93% “Light Ends” (most probably diethylenetriamine), 0.72% triethylenetetramine, 21.74% tetraethylene pentamine and 76.61% pentaethylene hexamine and higher (by weight). Another example of polyamine bottoms is one having an equivalent weight of 40.5 based on % N, sold as HPA-X by Union Carbide. These alkylene polyamine bottoms include cyclic condensation products such as piperazine and higher analogs of diethylenetriamine, triethylenetetramine and the like.
The carboxylic derivative compositions produced by reacting the carboxylic acylating agents of the invention and the amines described above are acylated amines which may include, for example, amine salts, amides, imides and imidazolines as well as mixtures thereof. To prepare the carboxylic derivative compositions from the amines, one or more of the carboxylic acylating agents and one or more amines are heated, optionally in the presence of a normally liquid, substantially inert organic liquid solvent/diluent, at temperatures in the range of from about 80� C. up to the decomposition point, i.e., the temperature at which any of the reactants or the product begins to decompose. Normally, temperatures in the range of from about 100� C. up to about 300� C. are used, provided 300� C. does not exceed the decomposition point. Temperatures of about 125� C. to about 250� C. are normally used.
R3—(OH)m wherein R3 is a monovalent or polyvalent organic radical joined to the —OH groups through carbon-to-oxygen bonds (that is, wherein the carbon is not part of a carbonyl group) and m is an integer of from 1 to about 10, usually 2 to about 6. As with the amine reactant, the alcohols can be aliphatic, cycloaliphatic, aromatic, and heterocyclic, including aliphatic-substituted cycloaliphatic alcohols, aliphatic-substituted aromatic alcohols, aliphatic-substituted heterocyclic alcohols, cycloaliphatic-substituted aliphatic alcohols, cycloaliphatic-substituted aromatic alcohols, cycloaliphatic-substituted heterocyclic alcohols, heterocyclic-substituted aliphatic alcohols, heterocyclic-substituted cycloaliphatic alcohols, and heterocyclic-substituted aromatic alcohols. Except for the polyoxyalkylene alcohols, the mono- and polyhydric alcohols corresponding to the above formula will usually contain not more than about 40 carbon atoms and generally not more than about 20 carbon atoms. The alcohols may contain non-hydrocarbon substituents of the same type mentioned with respect to the amines above, that is, non-hydrocarbon substituents which do not interfere with the reaction of the alcohols with the acylating agents of this invention. In general, polyhydric alcohols are preferred.
The alcohols may be polyoxyalkylene alcohols and derivatives thereof such as hydrocarbyl ethers thereof. Such polyoxyalkylene alcohols may be prepared by reacting, for example, a hydroxy-substituted compound, R4(OH)q wherein q is 1 to 6, preferably 2 to 3, and R4 is a residue of a mono- or polyhydric alcohol or mono- or polyhydroxy phenol, naphthol, etc., reacted with an alkylene oxide such as to form a hydrophobic base, R5 being a lower alkyl group of up to 4 carbon atoms, R6 being hydrogen or the same as R5 with the proviso that the alkylene oxide does not contain in excess of 10 carbon atoms. This base is then reacted with ethylene oxide to provide a hydrophilic portion resulting in a molecule having both hydrophobic and hydrophilic portions. Compounds illustrative of R4—(OH)q include aliphatic polyols such as alkylene glycols and alkane polyols such as ethylene glycol, propylene glycol, trimethylene glycol, glycerol, pentaerythritol, sorbitol, etc., and aromatic hydroxy compounds such as alkylated mono- and polyhydric phenols and naphthols such as cresol, heptylphenols, dodecylphenols, resorcinols, etc. The polyoxyalkylene alcohols and other alcohols useful in the process of the present invention are described in more detail in U.S. Pat. No. 4,234,435 (Meinhardt et al) in Cols. 29-32 and that disclosure is hereby incorporated by reference.
The acylating agents of this invention are reacted with the alcohols according to conventional esterification techniques. This normally involves heating the acylating agent of this invention with the alcohol, optionally in the presence of a normally liquid, substantially inert, organic liquid solvent/diluent and/or in the presence of esterification catalyst. Temperatures of at least about 100� C. up to the decomposition point are used (the decomposition point having been defined hereinbefore). This temperature is usually within the range of about 100� C. up to about 300� C. with temperatures of about 140� C. to 250� C. often being employed. Usually, at least about one-half equivalent of alcohol is used for each equivalent of acylating agent. An equivalent of acylating agent is the same as discussed above with respect to reaction with amines. An equivalent of alcohol is its molecular weight divided by the total number of hydroxyl groups present in the molecule. Thus, an equivalent weight of ethanol is its molecular weight while the equivalent weight of ethylene glycol is one-half its molecular weight.
A reactor is charged with 1000.9 parts of polyisobutene (Glissopal 2300, BASF) having 85% vinylidene content and a number average molecular weight of 2206 based on gel permeation chromatography, 100.8 parts of an ethylene-propylene-diene copolymer (Trilene 67, Uniroyal) having an equivalent weight of 1051 based on bromine number, and several drops of a kerosene solution of a polydimethylsiloxane antifoaming agent. The materials are heated under nitrogen atmosphere to 135� C., and a mixture of 85.8 parts of the methyl ester-methyl hemiacetal of glyoxylic acid (GMHA), having molecular weight of 120, and 2.45 parts of 70% solution of methanesulfonic acid in water, are added over 0.25 hour at 109 to 128� C. The materials are held at 135� C. for 6 hours. The reacted materials are filtered near 135� C. through diatomaceous earth. The filtrate has a saponification number of 26.5.
A reactor is charged with 301.6 parts of the filtrate from Example 1a having an equivalent weight of 2118 based on a saponification number of 26.5 and 206.5 parts of mineral oil diluent. The materials are heated under nitrogen atmosphere to 110� C., and 12.1 parts of polyethylenepolyamine bottoms, having an equivalent weight 42.4 based on a 33% N content, are added over 0.3 hour at 110� C. The materials are heated to 160� C., and held at 160� C. for 5 hours. The reacted materials are filtered near 160� C. through diatomaceous earth. The filtrate contains 0.75%N.
A reactor as in Example 1a is charged with 1000.9 parts of the polyisobutene and 50.21 parts of the ethylene-propylene-diene copolymer, each described in Example 1a, and several drops of a kerosene solution of a polydimethylsiloxane antifoaming agent. The materials are heated under nitrogen atmosphere to 100� C., and a mixture of 78.3 parts of the methyl ester-methyl hemiacetal of glyoxylic acid and 2.25 parts of 70% solution of methanesulfonic acid in water are added dropwise over 0.2 hour. The temperature is increased to 135� C. and is maintained at 135� C. for 6 hours. The reacted materials are filtered near 135� C. through diatomaceous earth. The filtrate has a saponification number of 26.56.
A reactor equipped for stripping of the contents is charged with 64.23 parts 50% aqueous glyoxylic acid followed by stripping off water at 75� C. at 100 mm Hg for 0.6 hour, then at 90 mm Hg for 0.25 hour, 80 mm Hg for 0.25 hour, and 70 mm Hg for 0.25 hour. The reactor is then equipped as in Example 1a. To the stripped materials are added 475 parts polyisobutene (Glissopal ES 3252, BASF) having Mn about 2400 and containing about 70 mole percent terminal vinylidene groups and 25 parts of the ethylene propylene-diene copolymer of Example 1a. The materials are heated to 85� C. to enable stirring whereupon 2 parts 70% aqueous methane sulfonic acid are added. An N2 purge is begun, the temperature is increased to 160� and is maintained for 2 hours. The materials are mixed with 131.3 parts mineral oil diluent. The product has saponification number=36.76 and contains 12.7% unreacted polyisobutylene (Thin layer chromatography (TLC)−Flame Ionization detector (FID)).
A reactor is charged with 310.5 parts of the product of Example 3a and 111 .7 parts mineral oil. The temperature is increased to 100� C. with N2 whereupon 12.35 parts of an ethylene polyamine mixture containing an average of 34% N are added over 0.2 hour. The temperature is maintained for 0.3 hour, is increased to 160� C. and is then maintained for 5 hours. The materials are filtered. The filtrate contains 0.81% N.
A reactor equipped for stripping is charged with 500.4 parts 50% aqueous glyoxylic acid which is then stripped as described in Example 3a. The reactor is then equipped as in Example 1a whereupon 3060 parts of Glissopal ES3252 and 540 parts Trilene 67 are added. The materials are heated to 110� C. at which time the materials can be stirred. To the materials are added 4.1 parts 70% aqueous methane sulfonic acid and N2 purge is begun. The materials are heated to 160� C. and the temperature is maintained for 3 hours. The mixture is beginning to become too viscous to stir; a total of 5757 parts mineral oil are added to facilitate stirring. The temperature is maintained at 160� for 5 hours, then the materials are filtered. The filtrate has saponification number 14.87.
A reactor is charged with 618 parts of the product of Example 7a which is then heated to 105� C. N2 blowing is begun, 28.1 parts of the amine of Example 3b is added over 0.2 hour, and after 0.3 hours the temperature is increased to 160� C. The temperature is maintained for 5 hours then the materials are filtered. The filtrate contains 1.3% N.
A reactor arranged for stripping of the contents is charged with 109.7 parts 50% aqueous glyoxylic acid which is then in increments as in Example 3a except the final increment is at 60 mn Hg for 0.3 hour. The reactor is then equipped as in Example 1a. To the stripped materials are added 30 parts Trilene 67, 525 parts Glissopal ES3252 and 45 parts of a 30 centistokes polybutene synthetic fluid (Amoco L-14). The materials are heated until they can be stirred (100� C.) and 2 parts 70% aqueous methane sulfonic acid are added. N2 blowing is begun, the temperature is increased to 160� C. and is maintained for 2.5 hours. The materials are mixed with 162.6 parts mineral oil and filtered. The filtrate has saponification number of 30.03.
A reactor is charged with 475 parts polyisobutylene (Ultravis 10, BP Chemicals) having {overscore (M)}n about 1000 and containing about 80 mole % terminal vinylidene groups, 25 parts Trilene 67 and 1 part 70% aqueous methane sulfonic acid. The materials are mixed and heated to 155� C. and 8 drops of a kerosene solution of a silicone antifoam agent are added. While maintaining 155� C., 95 parts of 50% aqueous glyoxylic acid are added dropwise over 4 hours. The temperature is increased to 160� C. and is maintained for 4 hours. The materials are mixed with 134 parts mineral oil and filtered. The filtrate has saponification no. 42.
A reactor is charged with 250 parts of the product of Example 10a and 206 parts mineral oil, then the materials are mixed and heated, under N2, to 100� C. To the heated mixture are added 11.5 parts HPA-X polyamine bottoms followed by mixing for 0.5 hour. The temperature is increased to 165� C. and is maintained for 5 hours. The materials are then filtered. Filtrate contains 0.85% N.
A reactor is charged with 1042.8 parts of Glissopal 2300, 74.04 parts of GMHA, 2.17 parts 70% aqueous methane sulfonic acid, and 10 drops of a silicone antifoam agent. The materials are heated to 135� C., under No. The temperature is maintained for 6 hours then the materials are filtered. Another reactor is charged with 303.02 parts of this filtrate which is heated to 110� C. under N2. To the heated materials are added, over 0.25 hour, 10.08 parts of polyethylenepolyamine bottoms, having an equivalent weight 42.4 based on a 33% N content. The materials are heated to 160� C. and are held at that temperature for 5 hours. The materials are filtered. The filtrate contains 0.55% N.
The effect of the additives is illustrated by the data in the tables. Viscosities are determined employing the procedure set out in ASTM Standard D-445 and the viscosity index is determined employing the procedure set out in ASTM Standard D-2270. ASTM Procedure D-445 covers, in general, the determination of kinematic viscosity of liquid petroleum products by measuring the time for a volume of liquid to flow under gravity through a calibrated glass capillary viscometer. These are reported in terms of centistokes, (abbreviated cSt). ASTM Procedure D-2270 provides a means for calculating Viscosity Index. Apparent viscosities are determined employing ASTM Procedure D-5293, Apparent Viscosities of Engine Oils Between −5 and −30� C. Using the Cold-Cranking Simulator and ASTM Procedure 4684, for temperatures between −15 and −35� C., as indicated. Apparent viscosities are reported in terms of centipoise (abbreviated cP) All of these Procedures appear in the Annual Book of ASTM Standards, Section 5, Petroleum Products. Lubricants and Fossil Fuels, ASTM, 1916 Race Street, Philadelphia, Pa., USA.
These Examples illustrate SAE 5W-30 engine oil compositions of this invention. They contains 11% of the indicated additive concentrate of this invention, 7.5% by weight of a 9% in oil solution of an olefin copolymer viscosity improver, 0.2% of Viscoplex� 1-330 (identified as a 50% in oil solution of a polymethacrylate pour point depressant, obtained from Rohm GMBH), in a mineral oil basestock made up of 95% 100 Neutral oil and 5% of 150 Neutral oil.
D5293 (−25� C.)
9.3 < cSt @ 100� C. < 12.5; cP @ −25� C. < 3500;
D5293 (−20� C.)
12.5 < cSt @ 100� C. < 16.3; cP @ −20� C. < 3500;
Comparing the data in Table 1 with that in Comp Table 1, and the data in Table 2 with that in Comp Table 2, it is seen that compositions of this invention provide superior 100� C. kinematic viscosities to lubricating oils than do compositions that do not include the acylated terpolymer component in the composition.
The compositions of this invention permit the preparation of lubricants meeting 100� C. kinematic viscosity standards when corresponding compositions derived solely from acylated polyolefin fail to meet minimum 100� C. kinematic viscosity requirements.
Patent CitationsCited PatentFiling datePublication dateApplicantTitleUS5674819 *Nov 9, 1995Oct 7, 1997The Lubrizol CorporationCarboxylic compositions, derivatives,lubricants, fuels and concentratesUS5681799May 3, 1995Oct 28, 1997Exxon Chemical Patents Inc.Ethylene alpha-olefin/diene interpolymer-substituted carboxylic acid dispersant additivesUS5696060 *Apr 15, 1996Dec 9, 1997The Lubrizol CorporationAcylated nitrogen compounds useful as additives for lubricating oil and fuel compositionsUS5696067 *Apr 15, 1996Dec 9, 1997The Lubrizol CorporationHydroxy-group containing acylated nitrogen compounds useful as additives for lubricating oil and fuel compositionsUS5739356 *Nov 21, 1996Apr 14, 1998The Lubrizol CorporationLactones useful as intermediates for preparing lubricating oil and fuel additivesUS5774742 *Feb 16, 1995Jun 30, 1998Hitachi, Ltd.Peripheral device using two microprocessors and two buses for automatically updating program after judging that update data is stored in a portable recording mediumUS5777142Aug 22, 1995Jul 7, 1998The Lubrizol CorporationUnsaturated hydroxycarboxylic compounds useful as intermediates for preparing lubricant and fuel additivesUS5777742 *Feb 4, 1994Jul 7, 1998Environmental Research Institute Of MichiganSystem and method for holographic imaging with discernible image of an objectUS5779742Aug 8, 1996Jul 14, 1998The Lubrizol CorporationAcylated nitrogen compounds useful as additives for lubricating oil and fuel compositionsUS5786490Apr 10, 1997Jul 28, 1998The Lubrizol CorporationProcess for preparing compositions useful as intermediates for preparing lubricating oil and fuel additivesUS5789490 *Oct 3, 1996Aug 4, 1998The Dow Chemical CompanyAmine capped polyethers and process for producing sameUS5840920 *Aug 8, 1996Nov 24, 1998The Lubrizol CorporationProcess for preparing compositions useful as intermediates for preparing lubricating oil and fuel additivesUS5851377 *Mar 10, 1997Dec 22, 1998The Lubrizol CorporationProcess of using acylated nitrogen compound petrochemical antifoulantsUS5851966 *Jun 5, 1997Dec 22, 1998The Lubrizol CorporationReaction products of substituted carboxylic acylating agents and carboxylic reactants for use in fuels and lubricantsUS5856279 *May 19, 1998Jan 5, 1999The Lubrizol CorporationAcylated nitrogen compounds useful as additives for lubricating oil and fuel compositionsUS5856524 *Dec 18, 1997Jan 5, 1999The Lubrizol CorporationProcess for preparing compositions useful as intermediates for preparing lubricating oil and fuel additivesUS5912213 *Jun 5, 1997Jun 15, 1999The Lubrizol CorporationSubstituted carboxylic acylating agent compositions and derivatives thereof for use in lubricants and fuelsEP0759443A2Aug 20, 1996Feb 26, 1997The Lubrizol CorporationHydroxy-substituted monolactones useful as intermediates for preparing lubricating oil and fuel additivesWO1998005741A1Aug 8, 1997Feb 12, 1998Lubrizol CorpProcess for preparing compositions useful as intermediates for preparing lubricating oil and fuel additives and derivatives thereof* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS6756348Nov 29, 2001Jun 29, 2004Chevron Oronite Company LlcLubricating oil having enhanced resistance to oxidation, nitration and viscosity increaseClassifications U.S. Classification508/222, 564/201, 508/305, 564/204, 508/454, 44/330International ClassificationC10L1/238, C10L10/00, C10L1/198, C08F8/00, C10M159/12, C10L1/18, C10M129/95, C10M133/52, C10M129/93, C10M145/10, C10L1/22Cooperative ClassificationC10M2215/22, C10N2240/106, C10N2240/101, C10M159/12, C10N2240/104, C10N2240/105, C10L10/00, C10M129/93, C10M2215/08, C10M2215/221, C10L1/198, C10M129/95, C10M133/52, C10L1/221, C10M2215/042, C10M2217/046, C10M2217/06, C10L1/1817, C10M2215/26, C10L1/238, C10M2215/225, C10M2215/082, C10M2215/226, C10M2215/04, C10M2215/30, C10M2215/28, C10N2240/10European ClassificationC08F8/00, C10L1/238, C10L1/198, C10M129/93, C10M133/52, C10L1/18W, C10M159/12, C10L1/22W, C10L10/00, C10M129/95Legal EventsDateCodeEventDescriptionMay 26, 2009FPExpired due to failure to pay maintenance feeEffective date: 20090403Apr 3, 2009LAPSLapse for failure to pay maintenance feesOct 13, 2008REMIMaintenance fee reminder mailedSep 23, 2004FPAYFee paymentYear of fee payment: 4Jul 27, 1998ASAssignmentOwner name: LUBRIZOL CORPORATION, THE, OHIOFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:PUDELSKI, JOHN K.;DIETZ, JEFFRY G.;SIVIK, MATTHEW R.;REEL/FRAME:009347/0769;SIGNING DATES FROM 19980724 TO 19980727RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services