US3714042A - Treated overbased complexes - Google Patents
Treated overbased complexes Download PDFInfo
- Publication number
- US3714042A US3714042A US00008701A US3714042DA US3714042A US 3714042 A US3714042 A US 3714042A US 00008701 A US00008701 A US 00008701A US 3714042D A US3714042D A US 3714042DA US 3714042 A US3714042 A US 3714042A
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- United States
- Prior art keywords
- composition
- complex
- sulfonate
- percent
- anhydride
- Prior art date
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Definitions
- ABSTRACT A Treat oyerbased complexes with high molecular cl-nll-i-clom lQH /2 4 Qm weight aliphatic carboxylic acids, anhydrides, esters,
- This invention relates to new compositions of matter, processes for preparing same, and lubricating compositions containing same. Particularly, it relates to the treatment of basic metal sulfonate complexes, sulfonate-carboxylate complexes and carboxylate complexes with high molecular weight carboxylic acids or derivatives thereof and the products resulting from said treatment. It relates also to the reduction of the foaming tendency of lubricating compositions containing these basic metal complexes.
- Basic metal complexes are well-known in the art. They are of utility as lubricant additives, paint-dryers, stabilizers for plastics, emulsifiers, rust preventives and the like. They are especially valuable because of their detergent or dispersant properties and their ability to neutralize undesirable acidic bodies formed in, e.g., crankcase lubricants under service conditions. For this reason they are one of the most commonly used lubricant additivesfThe incorporation of basic complexes into lubricating compositions in some cases gives rise to problems. Among these problems is the greater tendency of lubricating compositions containing detergent additives to foam. Another problem is that the lubricant compositions tend to form haze on standing.
- a further object is to provide basic metal complexes having improved oil-solubility.
- Another object of this invention is to provide lubricating compositions containing an improved basic metal complex.
- Another object is to provide a method of treating basic metal complexes to improve thefoam and solubility properties thereof.
- composition prepared by mixing (A) a basic metalcomplex selected from the class consisting of sulfonate, sulfonate-carboxylate and carboxylate complexes with up to an amount equivalent'to the total basicity thereof of (B) high molecular weight aliphatic carboxylic acid or anhydride wherein there are at least about aliphatic carbon atoms per carboxy group in (B) at a temperature of from about 25C to the decomposition temperature of the process mass.
- A a basic metalcomplex selected from the class consisting of sulfonate, sulfonate-carboxylate and carboxylate complexes with up to an amount equivalent'to the total basicity thereof of (B) high molecular weight aliphatic carboxylic acid or anhydride wherein there are at least about aliphatic carbon atoms per carboxy group in (B) at a temperature of from about 25C to the decomposition temperature of the process mass.
- complex refers to basic metal salts which contain metal in an amount in excess of that present in a neutral or normal metal salt.
- the metal ratio characterizing a complex is thus the ratio of the total equivalents of metal to the equivalents of metal in the form of neutral or normal metal.
- the base number of a complex is the number of milligrams of KOH to which one gram of the complex is equivalent as measured by titration.
- the metal of the complexes may be a Group 1 or Group 11 metal such as sodium, potassium, lithium, magnesium, strontium, barium, or calcium.
- An alkaline earth metal, especially calcium, barium, or magnesium is preferred.
- an oil-soluble sulfonic acid such as a synthetically prepared didodecylbenzene sulfonic acid
- an excess of lime e.g., 10 equivalents per equivalent of the acid
- a promoter such as methanol, heptylphenol, or mixture thereof
- a solvent such as mineral oil
- Another example is the preparation of a magnesium sulfonate complex by carbonating a mixture of a sulfonic acid or normal magnesium salt thereof, an excess of magnesium oxide, water, and preferably also an alcohol such as methanol.
- the carboxylic acids useful for preparing sulfonatecarboxylate complexes, and carboxylate complexes i.e., those obtainable from processes such as the above wherein a mixture of sulfonic acid and carboxylic acid or a carboxylic acid alone is used in lieu of the sulfonic acid, are oil-soluble acids and include primarily fatty acids which have at least about 12 aliphatic carbon atoms and not more than about 24 aliphatic carbon atoms; Examples of these acids include: palmitic, stearic, myristic, oleic,-linoleic, dodecanoic, behenic, etc.
- Cyclic carboxylic acids may also be employed. These include aromatic and cyclo-aliphatic acids.
- the aromatic acids are those containing a benzenoid structure (i.e., benzene, naphthalene, etc.) and an oil-solubilizing radical or radicals having a total of at least about 15 to 18 carbon atoms, preferably from about 15 to about 200 carbon atoms.
- Examples of the aromatic acids include: stearyl-benzoic acids, phenyl stearic acid, monoor polywax-substituted benzoic or naphthoic acids wherein the wax group consists of at least about 18 carbon atoms, cetyl hydroxybenzoic acids, etc.
- the cycloaliphatic acids contemplated have at least about 12, usually up to about 30 carbon atoms.
- Examples of such acids are petroleum naphthenic acids, cetyl cyclohexane carboxylic acids, di-lauryl decahydronaphthalene carboxylic acids, di-octyl cyclopentane carboxylic acids, etc.
- the thiocarboxylic acid analogs of the above acids, wherein one or both of the oxygen atoms of the carboxyl group are replaced by sulfur, are also contemplated.
- the ratio of the sulfonic acid to the carboxylic acid in mixtures is at least 1:1 (on a chemical equivalent basis) and is usually less than 5:1, preferably from 1:1 to 2:1.
- complexes having metal ratios from 1.1 to about 30 are contemplated for use in the present invention. Those having metal ratios ranging from 2 to 20 are preferred.
- An important aspect of the present invention is the treatment of a complex, after it is formed, with a high molecular weight carboxylic acid or anhydride or an acid-producing derivative thereof.
- high molecular weight carboxylic acid is meant an aliphatic acid wherein there is an average of at least about 25 aliphatic carbon atoms per carboxy radical.
- Such acids are exemplified by alkanoic and alkenoic acids as well as polar-substituted alkanoic or alkenoic acids. They may be either acyclic or cyclic and may contain aryl substituents.
- the polar substituents may be chloro, bromo, iodo, ether, nitro, or the like.
- the acids may contain one or more carboxy radicals, and may thus be dicarboxy, tri-carboxy, or tetracarboxy acids such as substituted succinic acids, maleic acids, malonic acids, etc.
- carboxy acids examples include those described in U.S. Pat. No. 3,219,666, the disclosure of which, particularly that at column 6, line 47 to column 7, line 55, is hereby incorporated by reference as a part of the specification.
- the high molecular weight hydrocarbon-substituted acids having at least about 50 aliphatic carbon atoms in the substituent, particularly those having from about 60 to about 5,000 aliphatic carbon atoms, are especially desirable for use herein.
- anhydrides and other acid-producing derivatives of the acids such as are described in U.S. Pat. No. 3,219,666.
- a particularly preferred class of high molecular weight carboxy compounds are the hydrocarbon-substituted succinic acids and anhydrides having from about 50, usually less than 5,000, aliphatic carbon atoms such as are described in U.S. Pat. No. 3,219,666. They include, for example, polyisobutenyl (760 molecular weight) succinic acid, polyisobutenyl (molecular weight of 900) succinic acid, polypropenyl (average molecular weight of 700) succinic anhydride, polyisobutyl (average molecular weight of 1,500) succinic acid.
- acids and derivatives are exemplified, by those obtained by the reaction of a halogenated hydrocarbon such as chlorinated polyisobutene (e.g., having molecular weight of 1,000) with an alpha, betaunsaturated acid-producingcompound such as acrylic acid, methacrylic acid, or methyl acrylate.
- a halogenated hydrocarbon such as chlorinated polyisobutene (e.g., having molecular weight of 1,000)
- an alpha, betaunsaturated acid-producingcompound such as acrylic acid, methacrylic acid, or methyl acrylate.
- compositions of this invention may be conducted at any temperature such as 25C up to the decomposition temperature of the process mixture.
- a solvent such as benzene, toluene, naphtha, or mineral oil is desirable in the process.
- the preferred mixing temperature is at least about 50C and below 250C.
- the usual temperature is from about 50C to about 150C.
- the amount of the high molecular weight carboxylic acid or anhydride used to treat the complex may be such as to be equivalent to the basicity (as measured by base numbers) of the basic metal complex. Often it is such as to be equivalent to 90 percent or less of the basicity of the complex; usually it is such as to be equivalent to 40 percent or less of basicity. In terms of weight proportions, as little as 0.1 percent, usually from 1 to percent and preferably from 3 to 5 percent (by weight of the complex) of the acid or derivative thereof is useful to accomplish the treatment.
- the corresponding amine salts, ammonium salts, imides, amides, and esters of the acids may be used in certain instances. in such instances, the proportions of the salts, amides, imides or esters to the complex are critical. Ordinarily, the proportion of such derivative should be such that it is equivalent to at least 1 but no more than 25percent, more often from 5 to 10 percent, of the basicity of the complex. Outside such range, the derivative is not effective as treatment of the complex for the purposes of this invention. Derivatives of the high molecular weight acids are described in U.S. Pat. Nos.
- the acylated nitrogen compositions disclosed in U.S. Pat. No. 3,219,666, particularly those derived from the high molecular weight succinic acids and ammonia, monoamines and alkylene polyamines and the esters disclosed in U.S. Pat. No. 3,381,022 are especially useful in the present invention.
- the temperature of the treatment should be at least about C, usually up to about 250C.
- a mineral oil solution of a basic, carbonated calcium complex is prepared by carbonating a mixture of an alkylated benzene sulfonic acid (molecular weight of 470) an alkylated calcium phenate, a mixture of lower alcohols (methanol, butanol, and pentanol) and excess lime (5.6 equivalents per equivalent of the acid).
- the solution has a sulfur content of 1.7 percent, a calcium content of 12.6 percent and a base number of 336.
- To 950 grams of the solution there is added 50 grams of a polyisobutene (molecular weight of l000)-substituted succinic anhydride (having a saponification number of 100) at 25C. The mixture is stirred, heated to C, held at that temperature for 0.5 hour, and filtered.
- the filtrate has a base number of 315 and contains 35.4 percent of mineral oil.
- EXAMPLE 2 To 950 grams of a solution of a basic, carbonated, calcium salt of an alkylated benzene sulfonic acid (average molecular weight 425) in mineral oil (base number 406, calcium 15.2 percent and sulfur 1.4 percent) there is added 50 grams of the polyisobutenyl succinic anhydride of Example 1 at 57C. The mixture is stirred for 0.65 hour at 5557C, then'at 152153C for 0.5 hour and filtered at 150C. The filtrate has a base number of 387 and contains 43.7 percent of mineral oil.
- EXAMPLE 3 A mixture comprising 753 parts (by weight) of mineral oil, 1440 parts of xylene, 84 parts of a mixture of a commercial fatty acid mixture (acid number of 200), 590 parts of an alkylated benzene sulfonic acid (average molecular weight 500), and 263 parts of magnesium oxide is heated to 60C. Methanol (360 parts) and water (180 parts) are added. The mixture is carbonated at 65C98C while methanol and water are being removed by azeotropic distillation. Additional water (180 parts) is then added and carbonation is continued at 87'90C for three and a half hours.
- EXAMPLE 5 To 950 grams of a mineral oil solution of a basic, carbonated calcium sulfonate complex of an alkylbenzene sulfonic acid (average molecular weight 440) (the complex containing 13.55 percent calcium, 1.81 percent sulfur and base number of 345), there is added 50 grams of a high molecular weight polyisobutenyl-substituted mono-carboxylic acid (having an acid number of 48 and prepared by heating a chlorinated polyisobutene having an average molecular weight of 1000 and a chlorine content of 4.3 percent with acrylic acid). The mixture is heated at 150-l60C while a stream of nitrogen is passed through it at 2 cubic feet per hour. The material is then filtered to give a composition having a base number of 318.
- a basic, carbonated calcium sulfonate complex of an alkylbenzene sulfonic acid average molecular weight 440
- EXAMPLE 6 A mixture comprising 906 grams (1.5 equivalents) of an oil solution of an alkylbenzene sulfonic acid (average molecular weight 460-480), 564 grams of mineral oil, 600 grams of toluene, 95.7 grams of magnesium oxide (4.4 equivalents), and 120 grams of water is carbonated at a temperature of about 78-85C for about 7 hours at a rate of about 3 cubic feet of carbon dioxide per hour. The carbonated product is stripped by heating to 165C at a pressure of mm (Hg) and filtered.
- an oil solution of an alkylbenzene sulfonic acid average molecular weight 460-480
- mineral oil 600 grams of toluene
- magnesium oxide 4.4 equivalents
- the filtrate is an oil solution of a basic, carbonated magnesium sulfonate complex having a metal ratio of 3.1 and containing 15.27 percent of magnesium sulfate ash, 2.66 percent of sulfur and a base number of 98.
- a basic, carbonated magnesium sulfonate complex having a metal ratio of 3.1 and containing 15.27 percent of magnesium sulfate ash, 2.66 percent of sulfur and a base number of 98.
- To v grams of this complex there is added 5 grams of the polyisobutenyl succinic anhydride of Example 1 and the mixture is stirred at 150C and filtered.
- EXAMPLE 7 To 950 grams of a solution of a basic, carbonated calcium sulfonate complex derived from mahogany sulfonic acid in mineral oil (containing 12.0 percent calcium, 1.78 percent sulfur and having a base number of 300), there is added 83 grams of a 60 percent mineral oil solution of an ammonium salt of a polyisobutenyl succinic acid containing 0.66 percent nitrogen. The mixture is heated at 160C for 0.5 hour. The residue is then filtered. The filtrate contains 24 percent oil.
- EXAMPLE 8 A solution of a basic, carbonated calcium complex of a mahogany sulfonic acid in mineral oil, containing 15.5 percent calcium, 1.35 percent sulfur and having a base number of 400 is mixed with 2 percent by weight of a mono-methyl ester of the polyisobutenyl succinic acid of the anhydride of Example 1 at -120C until a homogeneous mass is obtained.
- EXAMPLE 9 To 936 grams of a solution of a basic, carbonated calcium complex of an alkylbenzene sulfonic acid (average molecular weight 440) in mineral oil, containing 13.55 percent calcium, 1.81 percent sulfur and having a base number of 345 there is added 64 grams of a 78 percent solution of a polyisobutenyl succinimide in mineral oil (containing 1 percent nitrogen). The mixture is heated at l50l 60C for 1 hour and then filtered. The filtrate has a base number of 328, and contains 22.4 percent mineral oil.
- a basic, carbonated calcium complex of an alkylbenzene sulfonic acid average molecular weight 440
- mineral oil containing 13.55 percent calcium, 1.81 percent sulfur and having a base number of 345
- the mixture is heated at l50l 60C for 1 hour and then filtered.
- EXAMPLE 10 A mixture of 1,400 grams (10 equivalents of basic metal) of a solution of a basic, carbonated calcium complex of a petrosulfonic acid (average molecular weight 450) in mineral oil (containing 15.5 percent calcium, 1.35 percent sulfur and a base number of 400) and 1,650 grams (3 equivalents) of a polyisobutenyl succinic acid, having an acid number of 102 is prepared and heated at C until a homogeneous mass is obtained. The material is then filtered.
- EXAMPLE 1 l A mixture of 2,576 grams of mineral oil, 240 grams (1.85 equivalents) of octyl alcohol, 740 grams (20.0 equivalents) of calcium hydroxide, 2304 grams (8 equivalents) of oleic acid, and 392 grams (12.3 equivalents) of methyl alcohol is heated with stirring to a temperature about 50C. in about 0.5 hour. This mixture then is treated with C0 (3 cubic feet per hour) at 50-60C. for a period of about 3.5 hours. The resulting mixture is heated to 150C. and filtered. The filtrate is a basic calcium oleate complex having the following analyses:
- Example 1 The basic, carbonated calcium complex of Example 1 is replaced by this basic calcium oleate complex and the general procedure described in Example 1 for the treatment with polyisobutene-substituted succinic anhydride is followed.
- the product is a composition of this invention.
- compositions of this process can be employed as additives in lubricants intended for use in the automobile crankcases, transmissions, gears, chassis, torque converters, as well as in other automotive equipment, industrial machinery, construction industry equipment, railroad locomotives, and ships.
- Other suitable uses for these compositions are as additives in asphalt emulsions, and insecticidal compositions; as stabilizing agents for plasticizers and plastics; as additives in paints, rust-inhibiting compositions, slushing oils, cutting oils, flushing oils, and tanning compositions; as emulsifying agents, antiseptic cleaning compositions, fat-splitting compositions, and flotation agents; and as improving agents in fuels such as gasoline, fuel oils, gas oil, etc.
- the compositions When used as lubricating additives the compositions are usually present at concentrations ranging from about 0.1 to about 20 percent by weight of the lubricating composition. More particularly, the optimum concentration in crankcase lubricants for gasoline engines is usually from about 0.1 to about 10 percent by weight, and the optimum concentration in crankcase lubricants for diesel engines is usually from about 1 to about percent by weight. For use in fuels, the concentration may be as little as 0.0001 to about 2 percent by weight.
- the additives can be effectively employed in a variety of lubricating compositions based on diverse oils of lubricating viscosity such as a natural or synthetic lubricating oil, or suitable mixtures thereof.
- the lubricating compositions contemplated include principally crankcase lubricating oils for spark-ignited and compression-ignited internal combustion engines including automobile and truck engines, two-cycle engine lubricants, aviation piston engines, marine and railroad diesel engines, and the like.
- automatic transmission fluids, trans-axle lubricants, gear lubricants, metal-working lubricants, hydraulic fluids, and other lubricating oil and grease compositions can benefit from the incorporation of the present additives.
- Natural oils include animal oils and vegetable oils (e.g., castor oil, lard oil) as well as solvent-refined or acid-refined mineral lubricating oils of the paraffinic, naphthenic, or mixed paraffinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale are also useful base oils.
- Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, etc.); alkyl benzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di-(2-ethylhexyl)benzenes, etc.); polyphenyls (e.g., biphenyls, terphenyls, etc.); and the like.
- polymerized and interpolymerized olefins e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, etc.
- alkyl benzenes e
- Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of known synthetic lubricating oils. These are exemplified by the oils prepared through polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methylpolyisopropylene glycol ether having an average molecular weight of 1,000), diphenyl ether of polyethylene glycol having a molecular weight of SOD-1,000, diethyl ether of polypropylene glycol having a molecular weight of WOO-1,500, etc.) or monoand polycarboxylic esters thereof, for example, the acetic acid esters, mixed C -C fatty acid esters, or the C acid diester of tetraethylene glycol.
- the alkyl and aryl ethers of these polyoxyalkylene polymers e.g.,
- Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, etc.) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, pentaerythritol, etc.).
- dicarboxylic acids e.g., phthalic acid, succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, etc.
- alcohols e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, pentaerythrito
- esters include dibutyl adipate, di-(Z-ethylhexyl)sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, the complex ester formed by reacting one mole of sebacic acid with 2 moles of tetraethylene glycol and 2 moles of 2-ethylhexanoic acid, and the like.
- Silicon-based oils such as the polyalkyl-, and polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils comprise another useful class of synthetic lubricants (e.g., tetraethyl-silicate, tetraisopropyl-silicate, tetra-(2-ethylhexyl)-silicate, tetra-(4-methyl-2-tetraethyl)-silicate, tetra-(p-tertbutylpheny1)-si1icate, hexyl-(4-methyl-2-pentoxy)-disiloxane, poly(methyl)-siloxanes, poly(methylphenyl)- siloxanes, etc.).
- synthetic lubricants e.g., tetraethyl-silicate, tetraisopropyl-silicate, tetra-(2-ethyl
- Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decane phosphonic acid, etc.), polymeric tetrahydrofurans, and the like.
- additives may be present in the fuels and lubricants in which the composition of this invention is present.
- Such other additives include, for instance, supplemental detergents of the ash-containing or ashless type, viscosity improving agents, pour point depressing agents, supplemental anti-foam agents, extreme pressure agents, rust-inhibiting agents, oxidation inhibiting agents, friction improving agents, and corrosion inhibiting agents.
- the supplemental ash-containing detergents are exemplified by oil soluble neutral and basic salts of organic phosphorus acids characterized by at least one direct carbon-to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g., polyisobutene having a molecular weight of 1,000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride.
- the most commonly used salts of such acids are those of sodium, potassium, lithium, calcium, magnesium, strontium, and barium.
- the ashless detergents include acylated amines such as are described in US Pat. Nos. 3,172,892; 3,219,666; and 3,272,546.
- chlorinated aliphatic hydrocarbons such as chlorinated wax
- organic sulfides and polysulfides such as benzyl disulfide, bis(chlorobenzyl) disulfide, dibutyl tetrasulfide
- sulfurized sperm oil sulfurized methyl ester of oleic acid, sulfurized alkylphenol, sulfurized dipentene, and sulfurized terpene
- phosphosulfurized hydrocarbons such as the reaction product of a phosphorus sulfide with turpentine
- phosphorus esters including principally dihydrocarbon and trihydrocarbon phosphites such as dibutyl I phosphite, diheptyl' phosphite, dicyclohexyl phosphite, pentylphenyl phosphite, metal thiocarbamates such as zinc di
- Table I below shows the oil-solubility characteristics (in mineral oil) of the compositions of this invention (Test Samples I, Ill, V, and VII) and the complexes (Test Samples II, IV, VI and VIII) from which such compositionsare derived. A comparison of the results establishes the effectiveness of the high molecular weight carboxylic acids or derivatives to improve the oil-solubility of the metal complexes.
- Test Sample IX is included to show the ineffectiveness of a preformed metal salt of the high molecular weight carboxylic acid as a treatment of the complex.
- Example II shows the low foaming tendencies of the compositions of this invention by a test procedure which consists of three sequences, each sequence consisting of (a) air-blowing a mineral lubricating oil sample containing 2 percent by weight of an additive so as to generate some foam and measuring the amount of foam (in milliliters) immediately after the air-blowing and (b) repeating step (a) after the oil sample has been in storage for two weeks. Sequence 1) is carried out at room temperature and the storage temperature is room temperature. Sequence (2) is carried out at 200F on a fresh sample; the storage temperature is F. Sequence (3) is carried out at room temperature on the sample which has been tested in Sequence (2).
- Example 4 Complex from which Example 4 is prepared Sequence (I) Step (a) 0 0 Step (b) 0 460 Sequence (2) Step (a) 10 25 Step (b) I30 260 Sequence (3) Step (at) O 20 Step (b) 20 220
- the effectiveness of the lubricants containing compositions of this invention is shown by the Panel Coker Test.
- a 350 gram sample of the oil to be tested is placed in a coker reservoir having therein a splash mechanism, both reservoir and sample being at am bient temperatures, and a l.5 X 3.5 X 0.25 inches aluminum panel is suspended above the oil in such a manner as to hermetically sealthe reservoir.
- the oil reservoir temperature and the panel temperature are maintained at 240255F and 570590F, respectively, and the splash mechanism is operated for 13.5 minutes whereby the sample is splashed upon the sanded surface of the panel.
- the splash mechanism is then stopped and the panel is allowed to bake for l.5 minutes.
- the above cycle is repeated for a total of 4 hours at the end of which time the coker test mechanism is allowed to cool.
- the aluminum panel is then removed, washed with naphtha and inspected.
- the thermal stability of the oil sample being tested is measured by the panel inspection and is rated on the basis of the deposits which have accumulated on the aluminum panel. The results of the rating are indicated on a scale of l-O being indicative of complete absence of any such deposits and 0 being indicative of complete coverage of deposits on the panel).
- Samples (1) and (3) illustrate lubricants of Examples A and B above of the present invention whereas Samples (2) and (4) illustrate lubricants containing the metal complexes (referred to as A and B) from which the additives of Examples A and B are derived, respectively.
- EAch test sample contains sufficient additive to give a base number of 65.
- a composition prepared by a process comprising mixing (A) a basic metal complex selected from the class consisting of sulfonate, sulfonate-carboxylate and carboxylate complexes with up to an amount equivalent to the total basicity thereof of (B) a high molecular weight aliphatic carboxylicv acid or anhydride wherein there are at least about 25 aliphatic carbon atoms per carboxy group in (B) at a temperature of from about 25C to the decomposition temperature of the process mass.
- A a basic metal complex selected from the class consisting of sulfonate, sulfonate-carboxylate and carboxylate complexes with up to an amount equivalent to the total basicity thereof of (B) a high molecular weight aliphatic carboxylicv acid or anhydride wherein there are at least about 25 aliphatic carbon atoms per carboxy group in (B) at a temperature of from about 25C to the decomposition temperature of the process mass.
- composition of claim 1 wherein the metal is a Group 11 metal.
- composition of claim 2 wherein the basic metal complex is derived from an alkylated aryl sulfonic acid having at least about 15 aliphatic carbon atoms.
- composition of claim 3 wherein the carboxylic acid or anhydride of (B) is a polybutene substituted succinic acid or anhydride wherein the polybutene substituent has an average of at least about 50 carbon atoms and the amount thereof is from about 0.1 to about 10 percent by weight ofthe complex of (A).
- carboxylic acid or anhydride is a polyisobutenyl having a molecular weight from about 700 to about 5,000, succinic acid or anhydride and the amount thereof is from about 3 to about 5 percent by weight of the complex of (A).
- composition of claim 5 wherein the complex of(A) has a base number of at least about 70.
- composition of claim 7 wherein the basic calcium sulfonate complex is a mixture of (a) a carbonated, basic calcium alkylated benzene sulfonate having a base number of about 400 and (b) a carbonated, basic calcium alkylated benzene sulfonate having a base number of about in which the weight ratio of(a) to (b) is from about 10:1 to about 1:1.
- composition of claim 6 wherein the complex of (A) is a carbonated, basic magnesium sulfonate-carboxylate complex havin1a base number of from about 300 to about 500 and e temperature 18 from about 50C to about C.
- a composition prepared by a process comprising mixing (A) a basic metal complex selected from the class consisting of sulfonate, sulfonate-carboxylate and carboxylate complexes with (B) at least one member of the group consisting of substantially saturated hydrocarbon-substituted carboxylic acids, having at least about 25 aliphatic carbon atoms in the hydrocarbon substituent per carboxy group and the anhydrides, esters, ammonium salts, amine salts, amides, and imides thereof at a temperature of from about 50C to the decomposition temperature of the process mass, wherein the amount of the carboxylic acid or anhydride used is an amount equivalent to up to 40 percent of the basicity of the complex of (A), and the amount of the ester, ammonium salt, amine salt, amide, and imide derivative of the carboxylic acid used is an amount equivalent to at least 1 but no more than 25 percent of the basicity of the complex of (A).
- a process comprising the mixing of (A) a basic metal complex selected from the class consisting of sulfonate, sulfonate-carboxylate and carboxylate complexes with up to an amount equivalent to the basicity thereof of (B) a high molecular weight aliphatic carboxylic acid or anhydride wherein there are at least about 25 aliphatic carbon atoms per carboxy group in (B) at a temperature of from about 25C to the decomposition temperature of the process mass.
- A a basic metal complex selected from the class consisting of sulfonate, sulfonate-carboxylate and carboxylate complexes with up to an amount equivalent to the basicity thereof of (B) a high molecular weight aliphatic carboxylic acid or anhydride wherein there are at least about 25 aliphatic carbon atoms per carboxy group in (B) at a temperature of from about 25C to the decomposition temperature of the process mass.
- a lubricating composition comprising a major proportion of a lubricating oil and a minor foam reducing proportion of the composition of claim 1.
- a lubricating composition comprising a major proportion of a lubricating oil and a minor foam reducing proportion of the composition of claim 7.
- a lubricating composition comprising a major proportion of a lubricating oil and a minor foam reducing proportion of the composition of claim 8.
- a lubricating composition comprising a major proportion of a lubricating oil and a minor foam reducing proportion of the composition of claim 9.
- composition of claim 1 further characterized in that the temperature ranges from about 50C. and below 250C.
- the lubricating composition of claim 12 further characterized in that said lubricating oil contains about 0.1 to about 20% by weight of the composition.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81120469A | 1969-03-27 | 1969-03-27 | |
US870170A | 1970-02-04 | 1970-02-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3714042A true US3714042A (en) | 1973-01-30 |
Family
ID=26678496
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00008701A Expired - Lifetime US3714042A (en) | 1969-03-27 | 1970-02-04 | Treated overbased complexes |
Country Status (8)
Country | Link |
---|---|
US (1) | US3714042A (ja) |
JP (2) | JPS5020082B1 (ja) |
BE (1) | BE747995A (ja) |
CA (1) | CA966119A (ja) |
DE (1) | DE2014880A1 (ja) |
ES (1) | ES377937A1 (ja) |
FR (1) | FR2040023A5 (ja) |
GB (1) | GB1290251A (ja) |
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US4328111A (en) * | 1978-11-20 | 1982-05-04 | Standard Oil Company (Indiana) | Modified overbased sulfonates and phenates |
US4502970A (en) * | 1982-06-08 | 1985-03-05 | Exxon Research & Engineering Co. | Lubricating oil composition |
US4505830A (en) * | 1981-09-21 | 1985-03-19 | The Lubrizol Corporation | Metal working using lubricants containing basic alkali metal salts |
US4543195A (en) * | 1982-08-11 | 1985-09-24 | Elf France | Friction-reducing lubricating compositions each comprising an additive |
US4560488A (en) * | 1981-09-21 | 1985-12-24 | The Lubrizol Corporation | Metal working using lubricants containing basic alkali metal salts |
US4604138A (en) * | 1984-09-22 | 1986-08-05 | Thyssen Stahl Ag | Process for refining hot metal |
US4647387A (en) * | 1985-04-11 | 1987-03-03 | Witco Chemical Corp. | Succinic anhydride promoter overbased magnesium sulfonates and oils containing same |
WO1987005046A1 (en) * | 1986-02-19 | 1987-08-27 | The Lubrizol Corporation | Functional fluid with borated epoxides, carboylic solubilizers, zinc salts, and calcium complexes |
US4737298A (en) * | 1982-02-05 | 1988-04-12 | Institut Francais Du Petrole | Process for manufacturing soluble organic calcium complexes, the resultant complexes and their use, particularly as additives for improving the combustion of gas oils and fuel oils |
US4751011A (en) * | 1986-12-12 | 1988-06-14 | Exxon Chemical Patents Inc. | Hydrocarbon soluble complexes based on metal salts of polyolefinic dicarboxylic acids |
EP0294096A1 (en) * | 1987-05-26 | 1988-12-07 | Exxon Chemical Patents Inc. | Improved process for preparing stable oleaginous compositions |
EP0295108A1 (en) * | 1987-06-10 | 1988-12-14 | Exxon Chemical Patents Inc. | Corrosion inhibiting composition |
US4867890A (en) * | 1979-08-13 | 1989-09-19 | Terence Colclough | Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound |
US4869837A (en) * | 1987-07-09 | 1989-09-26 | Shell Oil Company | Preparation of a basic salt |
US5102566A (en) * | 1987-10-02 | 1992-04-07 | Exxon Chemical Patents Inc. | Low ash lubricant compositions for internal combustion engines (pt-727) |
US5108631A (en) * | 1987-09-23 | 1992-04-28 | The Lubrizol Corporation | Method of overbasing with a hydroxy sulfonic acid copromoter |
US5141657A (en) * | 1987-10-02 | 1992-08-25 | Exxon Chemical Patents Inc. | Lubricant compositions for internal combustion engines |
US5147917A (en) * | 1990-03-15 | 1992-09-15 | Asahi Denka Kogyo Kabushiki Kaisha | Halogenated resin composition |
US5213697A (en) * | 1989-04-20 | 1993-05-25 | The Lubrizol Corporation | Method for reducing friction between railroad wheel and railway track using metal overbased colloidal disperse systems |
AU638705B2 (en) * | 1989-04-20 | 1993-07-08 | Lubrizol Corporation, The | Methods for reducing friction between relatively slideable components using metal overbased colloidal disperse systems |
WO1993018119A1 (en) * | 1992-03-05 | 1993-09-16 | The Lubrizol Corporation | Overbased natural oils as additives for lubricants, plastics, paints, inks and greases |
WO1993024598A1 (en) * | 1992-06-04 | 1993-12-09 | The Lubrizol Corporation | Functional fluid with borated epoxides, carboxylic solubilizers, zinc salts, calcium complexes and sulfurized compositions |
US5284591A (en) * | 1991-05-15 | 1994-02-08 | The Lubrizol Corporation | Functional fluid with borated epoxides, carboxylic solubilizers, zinc salts, calcium complexes and sulfurized compositions |
US5320765A (en) * | 1987-10-02 | 1994-06-14 | Exxon Chemical Patents Inc. | Low ash lubricant compositions for internal combustion engines |
US5324440A (en) * | 1992-03-26 | 1994-06-28 | Institut Francais Du Petrole | Surbased colloidal product containing organic sulfur and their use as detergent additives having an antiwear and extreme-pressure effect in lubricating oils |
US5372738A (en) * | 1986-11-18 | 1994-12-13 | The Lubrizol Corporation | Water tolerance fixes in functional fluids and lubricants |
US5439604A (en) * | 1986-12-12 | 1995-08-08 | Exxon Chemical Patents Inc. | Oil soluble additives useful in oleaginous compositions |
US5441652A (en) * | 1988-06-14 | 1995-08-15 | Bp Chemicals (Additives) Limited | Process for the production of a lubricating oil additive concentrate |
US5470495A (en) * | 1992-11-18 | 1995-11-28 | Institut Francais Du Petrole | Colloidal products containing calcium and/or magnesium, as well as boron and/or phosphorus and/or sulfur, their preparation and their utilization as additives for lubricants |
US5501807A (en) * | 1991-10-14 | 1996-03-26 | Benda; Rainer | Overbased carboxylates |
US5519076A (en) * | 1994-02-24 | 1996-05-21 | Nissan Ferro Organic Chemical Co, Ltd. | Halogen-containing resin composition |
US5714443A (en) * | 1986-11-29 | 1998-02-03 | Bp Chemicals (Additives) Limited | Sulphurised alkaline earth metal hydrocarbyl phenates, their production and use thereof |
US5716914A (en) * | 1986-11-29 | 1998-02-10 | Bp International Limited | Alkaline earth metal hydrocarbyl phenates, their sulphurized derivatives, their production and use thereof |
US5756428A (en) * | 1986-10-16 | 1998-05-26 | Exxon Chemical Patents Inc. | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous composition |
US5883056A (en) * | 1995-02-28 | 1999-03-16 | Exxon Chemical Patents Inc. | Magnesium low base number sulphonates |
US6127321A (en) * | 1985-07-11 | 2000-10-03 | Exxon Chemical Patents Inc | Oil soluble dispersant additives useful in oleaginous compositions |
US6140279A (en) * | 1999-04-09 | 2000-10-31 | Exxon Chemical Patents Inc | Concentrates with high molecular weight dispersants and their preparation |
US6310010B1 (en) | 1998-04-09 | 2001-10-30 | Exxon Chemicals Patents Inc | High molecular weight dispersant compositions and their preparation |
US6403725B1 (en) | 1999-08-20 | 2002-06-11 | The Lubrizol Corporation | Metal containing dispersant polymers from condensation of polymers containing acidic group with overbased compositions containing reactive nucleophilic group |
US6569821B1 (en) * | 1999-01-04 | 2003-05-27 | Infineum Usa L.P. | Overbased metal detergents |
US20050075253A1 (en) * | 2003-10-02 | 2005-04-07 | Yushiro Chemical Industry Co., Ltd. | Water-soluble lubricant for warm or hot metal forming |
EP1624045A1 (en) * | 2004-08-05 | 2006-02-08 | Infineum International Limited | Lubricating oil additive concentrates |
EP2675876B1 (en) | 2011-02-17 | 2016-12-14 | The Lubrizol Corporation | Lubricants with good tbn retention |
WO2024047447A1 (en) | 2022-09-01 | 2024-03-07 | The Lubrizol Corporation | Gelling agent for calcium sulfonate greases |
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US4659488A (en) * | 1985-09-18 | 1987-04-21 | The Lubrizol Corporation | Metal working using lubricants containing basic alkaline earth metal salts |
EP0323087A1 (en) * | 1987-12-29 | 1989-07-05 | Exxon Chemical Patents Inc. | Improved overbased magnesium sulphonate |
DE4428641A1 (de) * | 1994-08-12 | 1996-02-15 | Basf Ag | Mesomorphe Komplexe aus Polyelektrolyten und Tensiden, Verfahren zu ihrer Herstellung sowie Filme, Folien, Fasern, Formkörper und Beschichtungen hieraus |
US5885944A (en) * | 1996-05-21 | 1999-03-23 | The Lubrizol Corporation | Low chlorine polyalkylene substituted carboxylic acylating agent compositions and compounds derived therefrom |
US6197075B1 (en) * | 1998-04-02 | 2001-03-06 | Crompton Corporation | Overbased magnesium deposit control additive for residual fuel oils |
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- 1970-03-26 CA CA078,463A patent/CA966119A/en not_active Expired
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Cited By (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3965017A (en) * | 1974-05-17 | 1976-06-22 | Exxon Research And Engineering Company | Lubricating oil compositions |
US4162986A (en) * | 1977-06-20 | 1979-07-31 | Mooney Chemicals, Inc. | Oil-soluble high metal content transitional metal organic oxy, hydroxy, complexes |
US4328111A (en) * | 1978-11-20 | 1982-05-04 | Standard Oil Company (Indiana) | Modified overbased sulfonates and phenates |
US4867890A (en) * | 1979-08-13 | 1989-09-19 | Terence Colclough | Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound |
EP0041851A2 (en) * | 1980-06-09 | 1981-12-16 | Exxon Research And Engineering Company | Lubricant composition with stabilized metal detergent additive and friction reducing ester component |
EP0041851A3 (en) * | 1980-06-09 | 1982-02-03 | Exxon Research And Engineering Company | Lubricant composition with stabilized metal detergent additive and friction reducing ester component |
US4505830A (en) * | 1981-09-21 | 1985-03-19 | The Lubrizol Corporation | Metal working using lubricants containing basic alkali metal salts |
US4560488A (en) * | 1981-09-21 | 1985-12-24 | The Lubrizol Corporation | Metal working using lubricants containing basic alkali metal salts |
US4737298A (en) * | 1982-02-05 | 1988-04-12 | Institut Francais Du Petrole | Process for manufacturing soluble organic calcium complexes, the resultant complexes and their use, particularly as additives for improving the combustion of gas oils and fuel oils |
US4502970A (en) * | 1982-06-08 | 1985-03-05 | Exxon Research & Engineering Co. | Lubricating oil composition |
US4543195A (en) * | 1982-08-11 | 1985-09-24 | Elf France | Friction-reducing lubricating compositions each comprising an additive |
US4604138A (en) * | 1984-09-22 | 1986-08-05 | Thyssen Stahl Ag | Process for refining hot metal |
US4647387A (en) * | 1985-04-11 | 1987-03-03 | Witco Chemical Corp. | Succinic anhydride promoter overbased magnesium sulfonates and oils containing same |
US6355074B1 (en) | 1985-07-11 | 2002-03-12 | Exxon Chemical Patents Inc | Oil soluble dispersant additives useful in oleaginous compositions |
US6127321A (en) * | 1985-07-11 | 2000-10-03 | Exxon Chemical Patents Inc | Oil soluble dispersant additives useful in oleaginous compositions |
WO1987005046A1 (en) * | 1986-02-19 | 1987-08-27 | The Lubrizol Corporation | Functional fluid with borated epoxides, carboylic solubilizers, zinc salts, and calcium complexes |
US5756428A (en) * | 1986-10-16 | 1998-05-26 | Exxon Chemical Patents Inc. | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous composition |
US5788722A (en) * | 1986-10-16 | 1998-08-04 | Exxon Chemical Patents Inc | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous compositions |
US5372738A (en) * | 1986-11-18 | 1994-12-13 | The Lubrizol Corporation | Water tolerance fixes in functional fluids and lubricants |
US6090759A (en) * | 1986-11-29 | 2000-07-18 | Lubrizol Adibis Holdings (Uk) Ltd. | Alkaline earth metal hydrocarbyl phenates, their sulphurized derivatives, their production and use thereof |
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Also Published As
Publication number | Publication date |
---|---|
JPS5335963B1 (ja) | 1978-09-29 |
DE2014880A1 (de) | 1970-10-01 |
ES377937A1 (es) | 1973-02-01 |
GB1290251A (ja) | 1972-09-27 |
CA966119A (en) | 1975-04-15 |
FR2040023A5 (ja) | 1971-01-15 |
BE747995A (fr) | 1970-09-28 |
JPS5020082B1 (ja) | 1975-07-11 |
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