EP0107282B1 - Schwefel enthaltende Schmiermittelzusammensetzungen - Google Patents

Schwefel enthaltende Schmiermittelzusammensetzungen Download PDF

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Publication number
EP0107282B1
EP0107282B1 EP83304628A EP83304628A EP0107282B1 EP 0107282 B1 EP0107282 B1 EP 0107282B1 EP 83304628 A EP83304628 A EP 83304628A EP 83304628 A EP83304628 A EP 83304628A EP 0107282 B1 EP0107282 B1 EP 0107282B1
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EP
European Patent Office
Prior art keywords
component
oil
sulfurization
oils
lubricating
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP83304628A
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English (en)
French (fr)
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EP0107282A2 (de
EP0107282A3 (en
Inventor
James Noel Vinci
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lubrizol Corp
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Lubrizol Corp
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Publication date
Application filed by Lubrizol Corp filed Critical Lubrizol Corp
Priority to AT83304628T priority Critical patent/ATE54163T1/de
Publication of EP0107282A2 publication Critical patent/EP0107282A2/de
Publication of EP0107282A3 publication Critical patent/EP0107282A3/en
Application granted granted Critical
Publication of EP0107282B1 publication Critical patent/EP0107282B1/de
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
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    • C10M127/00—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon
    • C10M127/02—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon well-defined aliphatic
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/40—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms monocarboxylic
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    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
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    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/083—Dibenzyl sulfide
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Definitions

  • This invention relates to lubricants based on hydrorefined lubricating oils, and, more particularly, to multipurpose industrial oils for use in gear, hydraulic and other specialty applications.
  • the invention relates to lubricating compositions comprising a major amount of a hydrorefined mineral lubricating oil and a minor amount of the combination of a fatty acid ester of glycerol wherein the fatty acid moiety contains olefinic unsaturation, and a sulfurized aliphatic olefinic compound containing from about 3-20 carbon atoms.
  • lubricant base oil stocks have been described in the prior art for preparing lubricating compositions. These include natural as well as synthetic oils. Natural oils include liquid petroleum oils and solvent-treated or acid-treated mineral oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale also are useful base oils. More recently, lubricant based stocks prepared by a hydrorefining process have been suggested as having advantages over solvent-extracted oils because the hydrorefining process is capable of producing new types of oils having modified structural and improved viscosimetric properties.
  • US Patent No. 3966623 describes lubricating compositions containing a synergistic corrosion- inhibiting combination of 2,5-bis-hydrocarbyldithio-1,3,4-thiadiazole and a primary alkyl or alkenyl amine salt of 2-mercaptobenzo-thiazole. These compositions may also contain other additives including inter alia Na z S-suifurized diisobutylene and prime lard oil. Compositions comprising a hydrorefined lubricating oil are not disclosed in US Patent 3966623.
  • US Patent No. 2830956 describes hydraulic power transmission fluids, particularly oil compositions, containing a number of diverse additives including inter alia sulfurized or unsulfurized fatty oils such as sulfurized sperm oil or sulfurized lard oil. The use of a combination of sulfurized and unsulfurized fatty oils is also mentioned. Compositions comprising a hydrorefined lubricating oil are not disclosed in US Patent No. 2830956.
  • a lubricating composition comprising:
  • the weight ratio of component (B) to component (C) is no greater than 1:1.
  • Such lubricant compositions derived from hydrorefined oils exhibit improved clarity, stability, extreme pressure properties, anti-wear capabilities and reduced staining of copper parts.
  • compositions of the invention which are described more fully below comprise at least three components;
  • Component (A) comprising a major amount of the composition is a hydrorefined mineral lubricating oil
  • Component (B) is at least one fatty acid ester of glycerol
  • Component (C) is the sulfurization product of at least one aliphatic olefinic hydrocarbon containing from about 3 to 20 carbon atoms.
  • Component (A) in the compositions of the invention is a hydrorefined lubricating oil.
  • Hydrorefining is a process for treating various oil stocks wherein an oil stock feed is combined with hydrogen and passed over a catalyst at elevated temperature and pressure. The extent of the treatment depends on the type of feedstock, the type of catalyst and the treating conditions. In the process, the hydrogen reacts with sulfur-containing compounds in the oil to form hydrogen sulfide and saturated hydrocarbons. The hydrogen also reacts with nitrogen-bearing compounds in the oil to form ammonia.
  • hydrorefining is particulalry useful for crude oils containing undesirable amounts of sulfur and nitrogen. Hydrorefining of oil feedstocks also results in improved color, neutralization, and some reduction in carbon residue.
  • Hydrorefining can be classified into two types depending on the desired results and intended use.
  • the hydrorefined stbkk may be used as feedstock for subsequent further processing, or the hydrotreated stock may be used as a base or blending shock for finished lubricants.
  • Hydrorefined oils of various types and viscosities are available from a variety of commercial sources since the process is used by most of the major oil refiners. Hydrorefined oil is desirable because of the reduction in undesirable sulfur and nitrogen content, improved color, improved stability and the relatively higher viscosity and natural viscosity index exhibited by such oils as compared to solvent refined oils.
  • One of the difficulties in using hydrorefined oil is that many chemical additives normally used in lubricating oils are not compatible with the hydrorefined oils and thus cannot be used.
  • oils are available from Gulf Canada under the general trade designation Paraflex. Particular oils are identified according to the ISO viscosity number which corresponds to the viscosity of the oil in centistokes at 40°C. Examples of such oils include Paraflex 10, Paraflex 100, Paraflex 460 (bright stock) and Paraflex 1000 (cylinder stock).
  • Component (B) in the compositions of the invention is at least one fatty acid ester of glycerol wherein the fatty acid moiety contains olefinic unsaturation.
  • fatty acid refers to acids which may be obtained by hydrolysis of naturally occurring vegetable or animal fats or oils. These fatty acids usually contain from 16 to 20 carbon atoms and are mixtures of saturated and unsaturated fatty acids.
  • the unsaturated fatty acids generally contained in the naturally occurring vegetable or animal fats and oils may contain one or more double bonds and such acids include palmitoleic acid, oleic acid, linoleic acid, linolenic acid, petroselenic acid, erucic acid, gadoleic acid, vaccenic acid, ricinoleic acid and minor amounts of compounds containing more than 20 carbon atoms such as behenic acid.
  • the unsaturated fatty acid moiety of the esters useful as component (B) may be derived for example from the mixtures of acids (or derivatives thereof) present in tall oil, peanut oil, soybean oil, cottonseed oil, sunflower seed oil, or wheat germ oil.
  • Tall oil is a mixture of rosin acids, mainly abeitic acid, and unsaturated fatty acids, mainly oleic and linoleic acids
  • Tall oil is a by-product of the sulfate process for the manufacture of wood pulp.
  • the compounds useful as component (B) in the compositions of the invention are fatty acid esters of glycerol which contain olefinic unsaturation in the fatty acid moiety.
  • the fatty oils that is, naturally occurring esters of glycerol with the fatty acids described above, and synthetic esters of similar structure.
  • naturally occurring fats and oils containing unsaturation include animal fats such as neat's-foot oil, lard oil, depot fat, beef tallow, etc.
  • Naturally occurring vegetable oils useful as component (B) include cottonseed oil, corn oil, poppy-seed oil, safflower oil, sesame oil, soybean oil, sunflower seed oil and wheat germ oil.
  • the fatty acid esters which are useful as component (B) in the invention also may be prepared from aliphatic olefinic acids of the type described above such as oleic acid, linoleic acid, linolenic acid, and behenic acid by reaction with glycerol.
  • Component (C) in the compositions of this invention is a sulfurization product of at least one aliphatic olefinic hydrocarbon compound containing about 3-20 carbon atoms.
  • the olefinic compounds which may be sulfurized to form component (C) are diverse in nature. They contain at least one olefinic double bond, which is defined as a non-aromatic double bond; that is, one connecting two aliphatic carbon atoms.
  • substituents in the substituted moieties described above is not normally a critical aspect of the invention and any such substituent is useful so long as it is or can be made compatible with lubricating environments and does not interfere under the contemplated reaction conditions.
  • substituted compounds which are so unstable as to deleteriously decompose under the reaction conditions employed are not contemplated.
  • certain substituents such as keto or aldehydo can desirably undergo sulfurization.
  • the selection of suitable substituents is within the skill of the art or may be established through routine testing.
  • substituentes include any of the above-listed moieties as well as hydroxy, carboxy, carbalkoxy, amidine, amino, sulfonyl, sulfinyl, sulfonate, nitro, phosphate, phosphite, alkali metal mercapto and the like.
  • the olefinic compound is usually one in which each R group which is not hydrogen is independently alkyl or alkenyl, or (less often) a corresponding substituted radical.
  • Monoolefinic and diolefinic compounds, particularly the former, are preferred, and especially terminal monoolefinic hydrocarbons; that is, those compounds in which R 3 and R 4 are hydrogen and R 1 and R 2 are alkyl (that is, the olefin is aliphatic).
  • Propylene, isobutene and their dimers, trimers and tetramers, and mixtures thereof are especially preferred olefinic compounds.
  • isobutene and diisobutene are particularly desirable because of their availability and the particularly high sulfur-containing compositions which can be prepared therefrom.
  • the sulfurizing reagent used for the preparation of component (C) is a mixture of hydrogen sulfide and sulfur.
  • the amounts of sulfur and hydrogen sulfide per mole of olefinic compound are, respectively, usually about 0.3-3.0 gram-atoms and about 0.1-1.5 moles.
  • the preferred ranges are about 0.5-2.0 gram-atoms and about 0.4­1.25 moles respectively, and the most desirable ranges are about 0.8-1.8 gram-atoms and about 0.4 ⁇ 0.8 mole respectively.
  • the temperature range in which the sulfurization reaction is carried out is generally about 50-350°C.
  • the preferred range is about 100-200 0 C, with about 125-180°C. being especially suitable.
  • the reaction is often preferably conducted under superatmospheric pressure; this may be and usually is autogenous pressure (i.e., the pressure which naturally develops during the course of the reaction) but may also be externally applied pressure.
  • autogenous pressure i.e., the pressure which naturally develops during the course of the reaction
  • the exact pressure developed during the reaction is dependent upon such factors as the design and operation of the system, the reaction temperature, and the vapor pressure of the reactants and products and it may vary during the course of the reaction.
  • the sulfurization reaction is effected in the presence of a sulfurization catalyst.
  • a sulfurization catalyst may be acidic, basic or neutral, but are preferably basic materials, especially nitrogen bases including ammonia and amines.
  • the amount of catalyst used is generally about 0.05-2.0% of the weight of the olefinic compound. In the case of the preferred ammonia and amine catalysts, about 0.0005-0.5 mole per mole of olefin is preferred, and about 0.001-0.1 mole is especially desirable.
  • a further optional step in the preparation of component (C) is the treatment of the sulfurized product, obtained as described hereinabove, to reduce active sulfur.
  • An illustrative method is treatment with an alkali metal sulfide as described in U.S. Patent 3,498,915.
  • Other optional treatments may be employed to remove insoluble by-products and improve such qualities as the odor, color and staining characteristics of the sulfurized compositions.
  • U.S. Patent 4,119,549 discloses suitable sulfurization products useful as component (C). Several specific sulfurized compositions are described in the working examples thereof. The following example illustrates the preparation of one such composition.
  • Sulfur (629 parts, 19.6 moles) is charged to a jacketed high-pressure reactor which is fitted with an agitator and internal cooling coils. Refrigerated brine is circulated through the coils to cool the reactor prior to the introduction of the gaseous reactants. After sealing the reactor, evacuating to about 800 Pa (6 torr) and cooling, 1100 parts (19.6 moles) of isobutene, 334 parts (9.8 moles) of hydrogen sulfide and 7 parts of n-butylamine are charged to the reactor. The reactor is heated using steam in the external jacket, to a temperature of about 171°C, over about 1.5 hours. A maximum pressure of 5 MPa (720 psig) is reached at about 138°C during this heat-up.
  • the pressure Prior to reaching the peak reaction temperature, the pressure starts to decrease and continues to decrease steadily as the gaseous reactants are consumed. After about 4.75 hours at about 171°C, the unreacted hydrogen sulfide and isobutene are vented to a recovery system. After the pressure in the reactor has decreased to atmospheric, the sulfurized mixture is recovered as a liquid.
  • the sulfurizing agent may be sulfur, and the reaction is effected by heating the olefinic compound with sulfur at a temperature of from 100-250°C, usually about 150-210°C with efficient agitation and in an inert atmosphere (e.g., nitrogen).
  • the wsight ratio of olefin to sulfur may be as high as 15:1 and is generally between about 5:1 and 10:1.
  • reaction mixture consist entirely of the olefin and sulfur
  • reaction may be effected in the presence of an inert solvent such as alcohol, ether, ester, aliphatic hydrocarbon or halogenated aromatic hydrocarbon which is a liquid at the reaction temperatures employed.
  • insoluble by-products may be remoed by filtration, usually at an elevated temperature (about 80-120°C).
  • the filtrate is the desired sulfurized product.
  • compositions of this invention typically contain components (B) and (C) in a weight ratio no greater than 1:1.
  • the weight ratio of component (B) to component (C) is from about 0.2:1 to about 1:1, and more preferably, from about 0.2:1 to about 0.5:1.
  • the following examples are illustrative of combinations of components (B) and (C) which are useful in the invention.
  • the lubricating compositions of this invention comprise a major amount of component (A) and a minor amount, generally from about 0.01 to 20% and preferably from about 0.01 to 10%, by weight of component (A) of the combination of components (B) and (C).
  • the lubricating compositions of the invention may be prepared merely by blending the oil and the components, or the components may be diluted in substantially inert diluents and thereafter blended with the hydrorefined oil.
  • the diluent if any, may be the oil used as a lubricant base and may include other additives such as those described hereinafter.
  • compositions of this invention are useful as industrial and gear lubricants.
  • the lubricants provide longer lasting extreme pressure properties, anti-wear capability and reduced staining of copper parts.
  • the lubricants of the invention can be used as crankcase lubricating oils for spark ignited and compression-ignited internal combustion engines, including automobile and truck engines, two-cycle engines, aviation piston engines, marine and railroad diesel engines, and the like. They can also be used in gas engines, stationary power engines and turbines and the like.
  • Automatic transmission fluids, transaxle lubricants, metal-working lubricants, hydraulic fluids and other lubricating oil and grease compositions can be prepared using the lubricant compositions of the present invention.
  • the lubricants of this invention based on hydrorefined oil may contain small amounts of synthetic oils and natural oils refined by other methods. Generally, however, there is little advantage in using oil which is not hydrorefined.
  • Natural oils include liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types.
  • 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, poly(1-hexenes), poly(1-octenes), poly(1-decenes) and mixtures thereof, etc.]; alkylbenzenes [e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes, etc.]; polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenols, etc.); alkylated diphenyl ethers and alkylated diphenyl sulfides and the derivatives, analogs and homologs thereof
  • 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 1000, diphenyl ether of polyethylene glycol having a molecular weight of 500-1000, diethyl ether of polypropylene glycol having a molecular weight of 1000-1500, etc.) or mono- and polycarboxylic esters thereof, for example, the acetic acid esters; mixed C 3 -C 8 fatty acid esters or the C 13 Oxo acid diester of tetraethylene glycol.
  • the oils prepared through polymerization of ethylene oxide or propylene oxide the alkyl and aryl
  • Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, furmaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acids, alkenyl malonic acids, etc.) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, etc.).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, furmaric acid, adipic acid
  • esters include dibutyladipate, di(2-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 two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid and the like.
  • Esters useful as synthetic oils also include those mde from C s to C 12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol, etc.
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxysiloxane 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-ethylhexyl) silicate, tetra-(p-tert-butylphenyl) silicate, hexa-(4-methyl-2-pentoxy)disiloxane, poly(methyl)siloxanes, poly(methylphenyl)siloxanes, etc.].
  • synthetic lubricants e.g., tetraethyl silicate, tetraisopropyl silicate, tetra(2-ethylhexyl) silicate, tetra-(4-methyl-2-
  • Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g. tricresyl phosphate, trioctyl phosphate, diethyl estter of decylphosphonic acid, etc.) and polymeric tetrahydrofurans and the like.
  • liquid esters of phosphorus-containing acids e.g. tricresyl phosphate, trioctyl phosphate, diethyl estter of decylphosphonic acid, etc.
  • polymeric tetrahydrofurans and the like e.g. tricresyl phosphate, trioctyl phosphate, diethyl estter of decylphosphonic acid, etc.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from retorting operations a petroleum oil obtained directly from distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
  • Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques are known to those of skill in the art such as solvent extraction, acid or base extraction, filtration percolation, etc.
  • Rerefined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in service. Such rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques directed to removal of spent additives and oil breakdown products.
  • the lubricants of the present invention contain an amount of the combination of components (A) and (B) sufficient to provide extreme pressure and anti-wear properties. Normally this amount will be about 0.01 to about 20%, preferably about 0.01 to about 10% of the total weight of the hydrorefined oil, component (A).
  • additives include, for example, detergents and dispersants of the ash-producing or ashless type, corrosion- and oxidation-inhibiting agents, pour point depressing agents, auxiliary extreme pressure agents, color stabilizers and anti-foam agents.
  • the ash-producing detergents are exemplified by oil-soluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acid, carboxylic acids, or 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 1000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pantasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride.
  • olefin polymer e.g., polyisobutene having a molecular weight of 1000
  • a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pantasulfide,
  • basic salt is used to designate metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical.
  • the commonly employed methods for preparing the basic salts involve heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature above 50°C and filtering the resulting mass.
  • a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide
  • Examples of compounds useful as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance; alcohols such as methanol, 2-propanol, octyl alcohol, cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; and amines such as aniline, phenylenediamine, phenothiazine, phenyl-(i-naphthylamine, and dodecylamine.
  • a particularly effective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent and at least one alcohol promoter, and carbonating the mixture at elevated temperatures such as 60-200 0 C.
  • Ashless detergents and dispersants are so called despite the fact that, depending on its constitution, the dispersant may upon combustion yield a non-volatile material such as boric oxide or phosphorus pentoxide; however, it does not ordinarily contain metal and therefore does not yueld a metal-containing ash on combustion.
  • a non-volatile material such as boric oxide or phosphorus pentoxide
  • Many types are known in the art, and any of them are suitable for use in the lubricants of this invention. The following are illustrative:
  • chlorinated aliphatic hydrocarbons such as chlorinated wax
  • aromatic sulfides and polysulfides such as benzyl disulfide, bis(chlorobenzyl)disulfide, bis-(chlorobenzyl)disulfide and sulfurized alkylphenol
  • phosphosulfurized hydro-carbons such as the reaction product of a phosphorus sulfide with turpentine or methyl oleate
  • phosphorus esters including principally dihydrocarbon and trihydrocarbon phosphites such as dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphite, pentylphenyl phosphite, dipentylphenyl phosphite, tridecyl phosphite, distearyl phosphite,
  • Components (B) and (C) can be added directly to the hydrorefined oil. Preferably, however, they are diluted with a substantially inert, normally liquid organic diluent such as mineral oil, naphtha, benzene, toluene or xylene, to form an additive concentrate.
  • a substantially inert, normally liquid organic diluent such as mineral oil, naphtha, benzene, toluene or xylene
  • These concentrates usually contain about 20-90% by weight of the combination of components (A) and (B) such as the compositions of Examples 2 and 3 and may contain, in addition, one or more other additives known in the art or described hereinabove.
  • Illustrative lubricants of this invention comprise principally a hydrorefined mineral oil in combination with about 0.1 to 10% by weight or more of the combinations of Examples 2 and 3 and with other known lubricant additives.
  • the following specific examples in Table II illustrate lubricating compositions according to the invention.
  • the lubricants of Examples 4-6 are prepared from concentrates of the indicated additives in a diluent oil.
  • the lubricants of Examples 4 and 5 are prepared by blending 98 parts of the hydrorefined oil with 2 parts of concentrate, and Example 6 is prepared by blending 97 parts of hydrorefined oil with 3 parts of the concentrate.

Claims (11)

1. Schmiermittel umfassend:
eine größere Menge von (A) einem hydroraffinierten Schmieröl, und
eine kleinere Menge einer Kombination von
(B) mindestens einem Fettsäureester von Glycerin, in dem die Fettsäureeinheit olefinisch ungesättigte Bindungen aufweist; und
(C) ein Sufurierungsprodukt von mindestens einer aliphatischen olefinischen Verbindung mit etwa 3 bis 20 Kohlenstoffatomen, das durch Umsetzung mit elementarem Schwefel und Schwefelwasserstoff in Gegenwart eines Sulfurierungskatalysators hergestellt worden ist.
2. Mittel nach Anspruch 1, in dem die Komponente (B) mindestens ein pflanzliches Öl ist.
3. Mittel nach Anspruch 2, in dem die Komponente (B) Sojabohnenöl ist.
4. Mittel nach einem der vorangehenden Ansprüche, in dem das Gewichtsverhältnis von Komponente (B) zu Komponente (C) nicht größer als 1:1 ist.
5. Mittel nach Anspruch 4, in dem das Gewichtsverhältnis von Komponente (B) zu Komponente (C) etwa 0,2:1 bis 0,5:1 beträgt.
6. Mittel nach einem der vorangehenden Ansprüche, in dem die Komponente (C) ein Sulfurierungsprodukt mindestens einer der Verbindungen Propylen, Isobutylen und Dimeren, Trimeren und Tetrameren davon ist.
7. Mittel nach Anspruch 6, in dem die Komponente (C) durch Umsetzung von Isobuten mit einem Gemisch aus Schwefel und Schwefelwasserstoff in Gegenwart eines Sulfierungskatalysators hergestellt worden ist.
8. Mittel nach einem der vorangehenden Ansprüche, in dem der Sulfurierungskatalysator ein basischer Katalysator ist.
9. Mittel nach Anspruch 9, in dem der Katalysator n-Butylamin ist.
10. Schmiermittel, umfassend:
eine größere Menge von (A) einem hydroraffinierten Schmieröl, und
etwa 0,01 bis 10 Gew.-% einer Kombination aus:
(B) Sojabohnenöl, und
(C) einem Sulfurierungsprodukt von mindestens einer der Verbindungen Propylen, Isobutylen und Dimeren, Trimeren und Tetrameren davon, das durch Umsetzung mit elementarem Schwefel und Schwefelwasserstoff in Gegenwart eines Sulfurierungskatalysators hergestellt worden ist, wobei das Gewichtsverhältnis von Komponente (B) zu Komponente (C) nicht größer als 1:1 ist.
11. Verfahren zur Herstellung eines Schmiermittels, umfassend das Vermischen von:
einer größeren Menge von (A) einem hydroraffinierten Schmieröl, und
einer kleineren Menge einer Kombination aus:
(B) mindestens einem Fettsäureester von Glycerin, in dem die Fettsäureeinheit olefinisch ungesättigte Bindungen enthält, und
(C) einem Sulfurierungsprodukt mindestens einer aliphatischen olefinischen Verbindung, die etwa 3 bis 20 Kohlenstoffatome enthält, das durch Umsetzung mit elementarem Schwefel und Schwefelwasserstoff in Gegenwart eines Sulfurierungskatalysators hergestellt worden ist.
EP83304628A 1982-10-28 1983-08-10 Schwefel enthaltende Schmiermittelzusammensetzungen Expired - Lifetime EP0107282B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83304628T ATE54163T1 (de) 1982-10-28 1983-08-10 Schwefel enthaltende schmiermittelzusammensetzungen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US43737782A 1982-10-28 1982-10-28
US437377 1982-10-28

Publications (3)

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EP0107282A2 EP0107282A2 (de) 1984-05-02
EP0107282A3 EP0107282A3 (en) 1985-08-07
EP0107282B1 true EP0107282B1 (de) 1990-06-27

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JP (1) JPS59135290A (de)
AT (1) ATE54163T1 (de)
AU (1) AU2065883A (de)
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DE (1) DE3381690D1 (de)
ES (1) ES8608033A1 (de)
HK (1) HK23191A (de)
ZA (1) ZA835289B (de)

Cited By (2)

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US6627584B2 (en) 2002-01-28 2003-09-30 Ethyl Corporation Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids
US7795365B2 (en) 2002-10-02 2010-09-14 Dow Global Technologies Inc. Liquid and gel-like low molecular weight ethylene polymers

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CA1248516A (en) * 1985-07-15 1989-01-10 Stephen C. Cohen Lubricating oil compositions containing novel combination of stabilizers
CA1290741C (en) * 1986-04-11 1991-10-15 James N. Vinci Grease and gear lubricant compositions comprising at least one metal-containing composition and at least one sulfurized organic compound
EP0289548B1 (de) * 1986-10-08 1992-07-22 The Lubrizol Corporation Sulfurierte zusammensetzungen und schmiermittel
WO1988003552A2 (en) * 1986-11-07 1988-05-19 The Lubrizol Corporation Sulfur-containing compositions, lubricant, fuel and functional fluid compositions
CA2025416C (en) * 1990-09-14 1999-06-22 Stephen Cedric Cohen Lubricating oil compositions containing novel combination of stabilizers (no. 2)
TW205067B (de) 1991-05-30 1993-05-01 Lubrizol Corp
US5244591A (en) * 1992-03-23 1993-09-14 Chevron Research And Technology Company Lubricating oil compositions for internal combustion engines having silver bearing parts
GB9415623D0 (en) * 1994-08-01 1994-09-21 Exxon Chemical Patents Inc Improvements in oleaginous compositions
US5641735A (en) * 1995-06-06 1997-06-24 Chevron Chemical Company Bis(thio)ethylene ashless wear inhibitors and lubricating oils
US6043200A (en) * 1995-07-31 2000-03-28 Exxon Chemical Patents, Inc. Oleaginous compositions
US5620949A (en) 1995-12-13 1997-04-15 The Lubrizol Corporation Condensation products of alkylphenols and aldehydes, and derivatives thereof
US5958849A (en) * 1997-01-03 1999-09-28 Exxon Research And Engineering Co. High performance metal working oil
CA2251418C (en) * 1997-10-30 2007-08-14 The Lubrizol Corporation A method to improve cu corrosion performance of mo-dtc and active sulfur by adding sunflower oil
EP3473694B1 (de) * 2017-10-12 2023-10-18 Infineum International Limited Schmierölzusammensetzungen

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US6627584B2 (en) 2002-01-28 2003-09-30 Ethyl Corporation Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids
US7795365B2 (en) 2002-10-02 2010-09-14 Dow Global Technologies Inc. Liquid and gel-like low molecular weight ethylene polymers

Also Published As

Publication number Publication date
HK23191A (en) 1991-04-04
EP0107282A2 (de) 1984-05-02
ES8608033A1 (es) 1986-06-01
DE3381690D1 (de) 1990-08-02
JPH0446319B2 (de) 1992-07-29
EP0107282A3 (en) 1985-08-07
CA1228847A (en) 1987-11-03
AU2065883A (en) 1984-05-03
ZA835289B (en) 1984-09-26
JPS59135290A (ja) 1984-08-03
ATE54163T1 (de) 1990-07-15
ES526787A0 (es) 1986-06-01

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