EP0330522B1 - Compositions démulsionnées d'huiles lubrifiantes - Google Patents

Compositions démulsionnées d'huiles lubrifiantes Download PDF

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Publication number
EP0330522B1
EP0330522B1 EP89301931A EP89301931A EP0330522B1 EP 0330522 B1 EP0330522 B1 EP 0330522B1 EP 89301931 A EP89301931 A EP 89301931A EP 89301931 A EP89301931 A EP 89301931A EP 0330522 B1 EP0330522 B1 EP 0330522B1
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EP
European Patent Office
Prior art keywords
additive
acid
oil soluble
groups
oil
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
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EP89301931A
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German (de)
English (en)
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EP0330522A3 (en
EP0330522A2 (fr
Inventor
Malcolm Waddoups
Jacob Emert
Laura Jean Colcord
Philip Merchant
Thomas John Pacansky
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ExxonMobil Chemical Patents Inc
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Exxon Chemical Patents Inc
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Publication of EP0330522A2 publication Critical patent/EP0330522A2/fr
Publication of EP0330522A3 publication Critical patent/EP0330522A3/en
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
    • 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
    • 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
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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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
    • C10M129/24—Aldehydes; Ketones
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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
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/50—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring monocarboxylic
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
    • C10M135/30—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups; Derivatives thereof
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    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
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    • C10N2040/34—Lubricating-sealants
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    • C10N2040/36—Release agents or mold release agents
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    • C10N2040/40—Generators or electric motors in oil or gas winning field
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    • C10N2040/44—Super vacuum or supercritical use
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    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to oleaginous compositions containing high molecular weight ashless dispersant and demulsifier additive having improved demulsibility.
  • Such concentrates are useful in oleaginous compositions, including fuel and lubricating oil compositions.
  • the Sequence IID is one of the established ASTM tests which define the current standard of crankcase lubricants for gasoline engines (American Society for Testing and Materials Special Technical Publication 315H, Part 1; September 15, 1979).
  • the test designed to evaluate the rust-preventive properties of the lubricant, creates an environment conducive to rust formation, in part by retaining water vapor from combustion gases in the crankcase with the use of a condenser at the crankcase breather outlet.
  • a by-product of the wet IID environment is the presence of conditions that are very conducive to emulsion formation.
  • emulsions would not necessarily be a matter of concern in themselves, the condenser tubes can become partially blocked with emulsion, leading to a pressure drop across the condenser and resultant pressure development in the crankcase.
  • Engine manufacturers have become concerned that oils which develop emulsions may also tend in the field to plug PCV valves or other lines associated with the crankcase ventilation system, and to coat other internal engine surfaces such as the rocker covers, valve deck, etc. with emulsion. These concerns are particularly directed to internal combustion engines wherein fresh air purge of the crankcase is not employed.
  • crankcase vapors are passed to an external separator intended to separate entrained liquids and vapors.
  • the separated liquids are intended to continuously drain back into the crankcase, and the gases passing through the separator are intended to be combined with air and/or fuel (or mixtures thereof) for charging to the engine's cylinder for combustion.
  • the presence of emulsion in the crankcase, and in the entrained vapors passing to the separator causes plugging of, or at least a buildup in the effective pressure drop across, the separator, decreasing its efficiency.
  • crankcase pressure beyond design limits, which, in turn, can cause oil seepage through crankcase seals, and other problems.
  • oil seepage through crankcase seals and other problems.
  • cold climates, and in short-trip or low-engine speed conditions the above problems may become more pronounced.
  • Crankcase lubricants for internal combustion engines are required to suspend solids resulting, e.g., from the inevitable oxidation of the oils components during operation of the engine, to minimize both the degree of deposits (e.g., varnish) on engine components and the formation of sludge.
  • modern crankcase lubricant formulations require the use of high levels of dispersancy (e.g., provided by use of high molecular weight dispersants or increased levels of lower molecular weight dispersants), and the use of other potent engine components, to minimize the adverse consequences on the engine of the oxidation of the lubricant during use.
  • US-A-3,509,052 discloses lubricating oil demulsifiers comprising certain alkylphenoxy poly(ethylene oxy) ethyl-mono- and diesters of phosphoric acid, polyoxyethylated amines, amides and quaternary salts, and polyoxyalkylene polyols and esters of such polyoxyalkylene polyols with lauric acid, stearic acid, succinic acid, and alkyl- or alkenyl-substituted succinic acids (up to 20 carbons in the alkyl or alkenyl group).
  • US-A-3,511,882 relates to crude oil petroleum demulsifiers prepared by adding a higher alkylene oxide, e.g., butylene oxide or propylene oxide, to a monohydric, dihydric or trihydric compound (e.g., propylene glycol). Thereafter ethylene oxide is added to the first adduct to form an oxyethylated adduct in which the proportion of primary hydroxyl groups to secondary hydroxyl groups is controlled. The oxyethylated adduct is then reacted with an epoxide of a polyphenol, preferably a diglycidyl ether of bis-phenol A.
  • a higher alkylene oxide e.g., butylene oxide or propylene oxide
  • ethylene oxide is added to the first adduct to form an oxyethylated adduct in which the proportion of primary hydroxyl groups to secondary hydroxyl groups is controlled.
  • the oxyethylated adduct is
  • Crude oil demulsifiers have heretofore been used in the breaking of crude petroleum oil emulsions (e.g. in down well applications) which comprise adducts obtained by reacting diglycidyl ether of bis-phenol A with polypropylene glycol and the propoxylated derivatives thereof.
  • lubricity additives compounds known as friction modifiers (also termed “lubricity additives”), which act to reduce the friction of internal engine parts and thereby increase fuel economy.
  • US-A-3,429,817 relates to the improvement of the lubricity and load carrying ability of a synthetic ester lubricating oil by addition of an ester formed by reacting about 2 moles of C2 to C5 glycol with about 1 mole of C36 dicarboxylic acid dimer of a C18 unsaturated fatty acid (e.g., linoleic acid or oleic acid).
  • US-A-4,479,883 relates to lubricating oil compositions having a relatively low level of phosphorous and improved friction reducting properties by use of a mixture of a glycol or glycerol ester of a polycarboxylic acid (e.g., linoleic acid dimers) with Mo, Zn, or Sb dithiocarbamates.
  • US-A-4,557,846 relates to lubricating oil friction reducing additives comprising oil soluble hydroxyamide compounds prepared by condensing a dimer carboxylic acid (e.g., linoleic acid dimers) with a hydroxyamine.
  • US-A-4,617,026 relates to fuel friction modifying additives comprising hydroxyl-containing esters of a C12 to C30 monocarboxylic acid and a glycol or trihydric alcohol, wherein the glycol can comprise polyalkylene glycols having 2 to 100 oxyalkylene repeat units.
  • US-A-4,683,069 relates to lubricating oil fuel economy additives comprising glycerol partial esters of C16-C18 fatty acids.
  • US-A-4,105,571 is directed to storage stable lubricating compositions having improved anti-friction and anti-wear properties containing a zinc dihydrocarbyldithiophosphate, an ester of a polycarboxylic acid and a glycol, and an ashless high molecular weight dispersant, wherein either the zinc or ester component, or both, are predispersed with the ashless dispersant prior to adding them to the lubricating composition.
  • the friction modifying esters are disclosed to include linoleic acid dimers which are esterified with glycol such as diethylene glycol.
  • US-A-4,388,201 discloses lubricating oil compositions containing such polycarboxylic acid-glycol friction modifier esters in combination with borated or non-borated alkenyl succinimide dispersants, which are stabilized by the addition of small proportions of a co-dispersant comprising an oil-soluble hydrocarbyl substituted mono- or bi-oxazoline or lactone oxazoline.
  • US-A-4,505,829 discloses lubricating oil compositions containing polycarboxylic acid glycol esters as friction modifiers in combination with hydrocarbon soluble alkenyl succinimide dispersants with reduced tendency towards formation of sediment upon storage.
  • the storage stability is improved by the addition thereto of small proportions of polyol or polyol anhydride partial esters of a fatty acid or an ethoxylated fatty acid, amine or amide compound.
  • US-A-4,617,134 relates to storage stable lubricating oil compositions comprising an additive combination of a polycarboxylic acid glycol or glycerol ester, as friction modifier, and zinc dihydrocarbyldithiophosphate and an ashless dispersant containing a selected amount of free hydroxyl groups.
  • the present invention provides an oil soluble mixture useful as an oil additive comprising:
  • the additive mixture may also include a metal detergent component (D) as defined hereafter.
  • the additive mixture in particular where the additive mixture is used in concentrates (otherwise referred to as packages), and especially where these contain a metal detergent component (D), the mixture comprises from 0.1 to 5 parts by weight (based on the weight of B) of a compatibility additive (C) comprising an ester or hydroxyamide of a mono- or polycarboxylic acid having a total of from 24 to 90 carbon atoms and at least one carboxylic acid group per molecule, with a mono-, di- or trihydric alcohol.
  • a compatibility additive C
  • C compatibility additive
  • the invention extends to a lubricating oil additive concentrate containing from 10 to 80 wt.% of an oil soluble mixture according as defined above dissolved in a hydrocarbon oil.
  • the concentrate may preferably comprise: from 3 to 45 wt.% of a said ashless dispersant (A)(1) from 0.01 to 3 wt.% of a said demulsifier additive (B) from 0.0005 to 2 wt.% of a said compatibility additive (C), and from 2 to 45 wt.% of a said metal detergent additive (D).
  • the invention also includes a process for forming a concentrate as described above wherein a said ashless dispersant (A)(1) and a said metal detergent component (D) are pre-mixed at 70 to 130°C, and wherein a said demulsifier additive (B) and a said compatibility additive (C) are separately mixed, and the separate mixtures are then mixed together.
  • the invention includes a lubricant composition
  • a lubricant composition comprising a concentrate as described above or obtainable by the process described above diluted with 3 to 100 parts by weight (per part by weight of concentrate) of lubricating oil.
  • the dispersant Component A of the oleaginous compositions of this invention can comprise one or more ashless dispersant materials, one or more polymeric viscosity index improver dispersants or mixtures thereof. Ashless dispersants and ashless dispersants admixed with polymeric viscosity index (V.I.) improver dispersants are particularly preferred.
  • V.I. polymeric viscosity index
  • the fully formulated lubricating oil is intended to contain both ashless dispersant and polymeric V.I. improver dispersant, generally they will be introduced to the final oil in separate additive concentrates, since the polymeric V.I. improver dispersants generally are not compatible with concentrates containing ashless dispersants, metal detergents, and many other conventional lubricant additives. Therefore, it will be understood that references herein to amounts and proportions of polymeric VI improver dispersants, unless otherwise indicated, are intended to refer to the final, fully formulated lubricating oil composition, rather than additive concentrates (to
  • the lubricating oil demulsifier additives of this invention are the water insoluble, at least partially oil soluble product of the reaction of (i) an alkylene oxide having from 2 to 10 carbon atoms and (ii) an adduct obtained by reacting a bis-epoxide, preferably a diglycidyl ether of bis-phenol A, and a polyhydric alcohol, preferably a polyoxyalkylene glycol.
  • a first adduct is made by reacting a bis-epoxide with a polyhydric alcohol.
  • the bis-epoxides are compounds containing at least two oxirane rings, i.e., These oxirane rings are connected or joined by hydrocarbon moieties or by hydrocarbon moieties containing at least one hetero atom or group (as defined hereinafter).
  • the hydrocarbon moieties contain from 1 to 100 carbon atoms. They include the alkylene, cycloalkylene, alkenylene, arylene, aralkenylene and alkarylene radicals.
  • Typical alkylene radicals are those containing from 1 to 100 carbon atoms, more typically from 1 to 50 carbon atoms.
  • the alkylene radicals may be straight chain or branched and may contain from 1 to 100 carbon atoms, preferably from 1 to 50 carbon atoms.
  • Typical cycloalkylene radicals are those containing from 4 to 16 ring carbon atoms.
  • the cycloalkylene radicals may contain alkyl substituents, e.g., C1-C8 alkyl, on one or more ring carbon atoms.
  • Typical arylene radicals are those containing from 6 to 12 ring carbons, e.g., phenylene, naphthylene and biphenylene.
  • Typical alkarylene and aralkylene radicals are those containing from 7 to 100 carbon atoms, preferably from 7 to 50 carbon atoms.
  • the hydrocarbon moieties joining the oxirane rings may contain substituent groups thereon.
  • the substituent groups are those which are substantially inert or unreactive at ambient conditions with the oxirane ring.
  • substantially inert and unreactive at ambient conditions is intended to mean that the atom or group is substantially inert to chemical reactions at ambient temperatures and pressure with the oxirane ring so as not to materially interfere in an adverse manner with the preparation and/or functioning of the compositions, additives, compounds. of this invention in the context of its intended use. For example, small amounts of these atoms or groups can undergo minimal reaction with the oxirane ring without preventing the making and using of the invention as described herein.
  • Suitable substituent groups are alkyl groups, hydroxyl groups, tertiary amino groups and halogens. When more than one substituent is present they may be the same or different.
  • substituent groups are substantially inert or unreactive at ambient conditions with the oxirane ring, they will react with the oxirane ring under conditions effective to allow reaction of the oxirane ring with the reactive hydroxy groups of the polyhydric alcohols. Whether these groups are suitable substituent groups which can be present on the bis-epoxide depends, in part, upon their reactivity with the oxirane ring. Generally, if they are substantially more reactive with the oxirane ring than the oxirane ring is with the reactive hydroxy group, they will tend to materially interfere in an adverse manner with the preparation of the intended demulsifiers of this invention and are, therefore, unsuitable.
  • Suitable hetero atoms or groups which may be in the carbon chain of the hydrocarbon moiety are: oxygen atoms (i.e., -O- or ether linkages in the carbon chain); sulfur atoms (i.e. -S- or thioether linkages in the carbon chain); carboxy groups (i.e., sulfonyl group (i.e., ketone group (i.e., sulfinyl group (i.e., an oxirane ring (i.e., and nitro group.
  • oxygen atoms i.e., -O- or ether linkages in the carbon chain
  • sulfur atoms i.e. -S- or thioether linkages in the carbon chain
  • carboxy groups i.e., sulfonyl group (i.e., ketone group (i.e., sulfinyl group (i.e., an oxirane ring (i.e., and nitro group
  • the bis-epoxides of the present invention contain at least two oxirane rings or epoxide moieties. It is critical that the bis-epoxide contain at least two oxirane rings in the same molecule.
  • the bis-epoxides useful in the instant invention are well known in the art and are generally commercially available or may readily be prepared by conventional and well known methods.
  • the bis-epoxides include those represented by the general formula wherein: R is a divalent hydrocarbon radical, a substituted divalent hydrocarbon radical, a divalent hydrocarbon radical containing at least one hetero atom or group, and a substituted divalent hydrocarbon radical containing at least one hetero atom or group; R1 and R6 are independently selected from hydrogen, monovalent hydrocarbon radicals, substituted monovalent hydrocarbon radicals, monovalent hydrocarbon radicals containing at least one hetero atom or group, substituted monovalent hydrocarbon radicals containing at least one hetero atom or group, and oxirane containing radicals; R2 and R3 are independently selected from hydrogen, monovalent hydrocarbon radicals, substituted monovalent hydrocarbon radicals, monovalent hydrocarbon radicals containing at least one hetero atom or group, substituted monovalent hydrocarbon radicals containing at least one hetero atom or group, monovalent oxirane containing radicals, divalent hydrocarbon radicals, and substituted divalent hydrocarbon radicals, with the proviso that if R2 or R3
  • the monovalent hydrocarbon radicals represented by R1 - R6 generally contain from 1 to 100 carbon atoms. These hydrocarbon radicals include alkyl, alkenyl, cycloalkyl, aryl, aralkyl, and alkaryl radicals.
  • the alkyl radicals may contain from 1 to 100, preferably from 1 to 50, carbon atoms and may be straight chain or branched.
  • the alkenyl radicals may contain from 2 to 100 carbons, preferably from 2 to 50 carbon atoms, and may be straight chain or branched.
  • Preferred cycloalkyl radicals are those containing from 4 to 12 ring carbon atoms, e.g., cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl. These cycloalkyl radicals may contain substituent groups, preferably alkyl groups, on the ring carbon atoms, e.g., methylcyclohexyl, 1,3-dimethylcyclopentyl.
  • the preferred alkenyl radicals are those containing from 2 to 30 carbon atoms, e.g., ethenyl, 1-propenyl, 2-propenyl.
  • the preferred aryl radicals are those containing from 6 to 12 ring carbon atoms, i.e., phenyl, naphthyl, and biphenyl.
  • the preferred aralkyl and alkaryl radicals are those containing from 7 to 30 carbon atoms, e.g., p-tolyl, 2,6-xylyl, 2,4,6-trimethylphenyl, 2-isopropylphenyl, benzyl, 2-phenylethyl, 4-phenylbutyl.
  • the substituted monovalent hydrocarbon radicals represented by R1 - R6 are the monovalent hydrocarbon radicals described hereinafore which contain at least one substituent group thereon.
  • the substituent groups are such that they are substantially unreactive under ambient conditions with the oxirane moieties. When more than one substituent group is present they may be the same or different.
  • the monovalent hydrocarbon radicals containing at least one hetero atom or group are the monovalent hydrocarbon radicals described hereinafore which contain at least one hetero atom or group in the carbon chain.
  • the hetero atom or group is separated from the carbon of the oxirane ring by at least one intervening carbon atom. When more than one hetero atom or group is present they may be the same or different.
  • the hetero atoms or groups are those that are substantially unreactive under ambient conditions with the oxirane ring. These hetero atoms or groups are those described hereinafore.
  • the substituted monovalent hydrocarbon radicals containing at least one hetero atom or group are the substituted monovalent hydrocarbon radicals containing at least one hetero atom or group described above which contain at least one substituent group on at least one carbon atom.
  • the substituent groups are those described hereinafore.
  • the oxirane radicals represented by R1 - R6 may be represented by the formula wherein: R7 has the same meaning as R1, R8 - R9 have the same meaning as R2 - R3, and R10 has the same meaning as R in Formula V.
  • the divalent hydrocarbon radicals represented by R2 - R5 and R8 - R9 generally are aliphatic acyclic radicals and contain from 1 to 5 carbon atoms.
  • Preferred divalent hydrocarbon radicals are the alkylene radicals.
  • Preferred alkylene radicals are those that, together with the two carbon atoms of the oxirane ring, form a cyclic structure containing from 4 to 8 ring carbon atoms.
  • R3 and R4 are both ethylene radicals
  • the resultant cyclic structure formed with the two carbon atoms of the oxirane ring is a cyclohexylene oxide, i.e.,
  • the divalent substituted hydrocarbon radicals represented by R2 - R5 and R8 - R9 are the divalent hydrocarbon radicals described above which contain at least one substituent group on at least one carbon atom.
  • the divalent hydrocarbon radicals represented by R and R10 generally contain from 1 to 100 carbon atoms, preferably from 1 to 50 carbon atoms. They may be aliphatic, aromatic or aliphatic-aromatic. If theyare aliphatic they may be saturated or unsaturated, acyclic or alicyclic. They include alkylene, cycloalkylene, alkenylene, arylene, aralkylene, and alkarylene radicals. The alkylene radicals may be straight chain or branched.
  • Preferred alkylene radicals are those containing from 1 to 50 carbon atoms.
  • Preferred alkenylene radicals are those containing from 2 to 50 carbon atoms.
  • Preferred cycloalkylene radicals are those containing from 4 to 12 ring carbon atoms.
  • the cycloalkylene radicals may contain substituents, preferably alkyls, on the ring carbon atoms.
  • arylene as used in the specification and the appended claims is not intended to limit the divalent aromatic moiety represented by R and R10 to benzene. Accordingly, it is to be understood that the divalent aromatic moiety can be a single aromatic nucleus such as a benzene nucleus, a pyridine nucleus, a thiophene nucleus, a 1,2,3,4-tetra-hydronaphthalene nucleus, etc., or a poly-nuclear aromatic moiety.
  • Such polynuclear moieties can be of the fused type; that is, wherein at least one aromatic nucleus is fused at two points to another nucleus such as found in naphthalene, anthracene, the azanaphthalenes.
  • polynuclear aromatic moieties can be of the linked type wherein at least two nuclei (either mono- or polynuclear) are linked through bridging linkages to each other.
  • Such bridging linkages can be chosen from the group consisting of carbon-to-carbon single bonds, ether linkages, keto linkages, sulfide linkages, polysulfide linkages of 2 to 6 sulfur atoms, sulfinyl linkages, sulfonyl linkages, methylene linkages, alkylene linkages, di-(lower alkyl)-methylene linkages, lower alkylene ether linkages, alkylene keto linkages, lower alkylene sulfur linkages, lower alkylene polysulfide linkages of 2 to 6 carbon atoms, amino linkages, polyamino linkages and mixtures of such divalent bridging linkages.
  • Ar is a linked polynuclear aromatic moiety it can be represented by the general formula - Ar(Lng-Ar) r - wherein r is an integer of 1 to 10, preferably 1 to 8, more preferably 1, 2 or 3; Ar is a divalent aromatic moiety as described above, and each Lng is a bridging linkage individually chosen from the group consisting of carbon-to-carbon single bonds, ether linkages (e.g.
  • keto linkages e.g., sulfide linkages (e.g., -S-), polysulfide linkages of 2 to 6 sulfur atoms (e.g., -S2-), sulfinyl linkages (e.g., -S (0) -) , sulfonyl linkages (e.g., --S (0)2 -) , lower alkylene linkages (e.g., -CH2-, -CH2 - CH2-, etc.), di (lower alkyl) -methylene linkages (e.g., - CR * 2-), lower alkylene ether linkages (e.g., - CH2 - 0 -, -CH2 - 0 - CH2 -, -CH2 - CH2 - 0 -, -CH2CH20CH2CH2 -, .) lower alkylene sulfide linkages (e.g., wherein one or
  • R12 and R13 are independently selected from hydrogen and alkyl radicals, preferably alkyl radicals containing from 1 to 20 carbon atoms;
  • R11 is selected from alkylene, alkylidene, cycloalkylene, and cycloalkylidene radicals; and
  • u and u1 are independently selected from integers having a value of from 1 to 4.
  • divalent substituted hydrocarbon radicals containing at least one hetero atom or group include: Also included within the scope of the bis-epoxides of the instant invention are these represented by the formula (VII) wherein: R and R1-R3 are as defined hereinafore; R14 and R15 independently have the same meaning as R1; X is an aromatic moiety; R16 and R17 are independently selected from divalent aliphatic acyclic hydrocarbon radicals and divalent substituted aliphatic acyclic hydrocarbon radicals which together with the two carbon atoms of the oxirane ring and the two adjacent ring carbon atoms of the aromatic moiety X form a cyclic structure; m and m1 are independently zero or one with the proviso that the sum of m plus m1 is at least one; and p is zero or one.
  • the aromatic moieties represented by X are preferably those containing from 6 to 12 ring carbon atoms, e.g., benzene, napthalene, and biphenyl.
  • the aromatic moieties may contain one or more substituents on one or more ring carbon atoms. These substituents are those which are substantially unreactive at ambient conditions, e.g., temperature and pressure, with the oxirane ring. They include, for example, alkyl, hydroxyl, nitro, and the like.
  • bis-epoxides of the instant invention are those represented by the formula (VIII): wherein: R, R1-R3, R14-R15 and p are as defined hereinafore; and R18 is independently selected from divalent hydrocarbon radicals or a substituted divalent hydrocarbon radicals which together with the two carbon atoms of the oxirane ring forms a cyclic preferably cycloaliphatic, structure.
  • the divalent hydrocarbon or substituted divalent hydrocarbon radicals represented by R18 preferably contain from 2 to 14 carbon atoms so as to form, together with the two carbon atoms of the oxirane ring, a 4 to 16 membered ring structure, preferably a cycloaliphatic ring.
  • the preferred divalent hydrocarbon radicals are the divalent aliphatic hydrocarbon radicals, preferably the alkylene radicals.
  • the divalent aliphatic hydrocarbon radicals represented by R18 may contain one or more substituent groups on one or more ring carbon atoms.
  • the substituents are selected from those that are substantially unreactive under ambient conditions with the oxirane ring, e.g., alkyl, hydroxyl, and the like.
  • the bis-epoxides useful in the instant invention also include the epoxy resins. These epoxy resins are well known in the art and are generally commercially available. They are described, for example, in Billmeyer, F. W. Jr., Textbook of Polymer Science, 2nd edition, Wiley-Interscience, New York, 1971, pp. 479-480; Lee, H and Neville, K., "Epoxy Resins", pp. 209-271 in Mark, H. F., Gaylord, N. G. and Bikales, N. M., eds., Encyclopedia of Polymer Science and Technology, Vol. 6, Interscience Div., John Wiley and Sons, New York, 1967; and in US-A-Nos. 3,477,990 and 3,408,422.
  • the epoxy resins include those compounds possessing one or two terminal epoxy groups. These bis-epoxides are saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or heterocyclic, and are substituted, if desired, with non-interfering substituents, such as halogen atoms, hydroxyl groups, ether radicals, and the like.
  • Preferred bis-epoxides are the glycidyl polyethers of polyhydric phenols and polyhydric alcohols, especially the glycidyl polyethers of 2,2-bis(4-hydroxyphenyl) propane having an average molecular weight between 300 and 3,000 and an epoxide equivalent weight (WPE) between 140 and 2,000.
  • WPE epoxide equivalent weight
  • Especially preferred are the diglycidyl polyethers of 2,2-bis(4-hydroxyphenyl) propane having a WPE between 140 and 500 and an average molecular weight of from 300 to 900.
  • suitable epoxy compounds include those compounds derived from polyhydric phenols and having at least one vicinal epoxy group wherein the carbon-to-carbon bonds within the six-membered ring are saturated.
  • Such epoxy resins may be obtained by at least two well-known techniques, i.e., by the hydrogenation of glycidyl polyethers of polyhydric phenols or (2) by the reaction of hydrogenated polyhydric phenols with epichlorohydrin in the presence of a suitable catalyst such as Lewis acids, i.e., boron trihalides and complexes thereof, and subsequent dehydrochlorination in an alkaline medium.
  • a suitable catalyst such as Lewis acids, i.e., boron trihalides and complexes thereof, and subsequent dehydrochlorination in an alkaline medium.
  • the method of preparation forms no part of the present invention and the resulting saturated epoxy resins derived by either method are suitable in the present compositions.
  • the first method comprises the hydrogenation of glycidyl polyethers of polyhydric phenols with hydrogen in the presence of a catalyst consisting of rhodium and/or ruthenium supported on an inert carrier at a temperature below about 50°C.
  • a catalyst consisting of rhodium and/or ruthenium supported on an inert carrier at a temperature below about 50°C.
  • the hydrogenated epoxy compounds prepared by the process disclosed in US-A-3,336,241 are suitable for use in the present compositions.
  • saturated epoxy resin as used herein shall be deemed to mean the glycidyl ethers of polyhydric phenols wherein the aromatic ring structure of the phenols have been or are saturated.
  • One class of useful epoxy resins are those prepared by condensing epichlorohydrin with bisphenol-A. They include resins represented by the general structural formula (IX): wherein: R1-R6 are defined hereinafore, and preferably are all hydrogen; R20 is independently selected from alkyl radicals, preferably alkyl radicals containing from 1 to 10 carbon atoms, hydroxyl, or halogen radicals; R21 is independently selected from alkyl radicals, preferably alkyl radicals containing from 1 to 10 carbon atoms, hydroxyl, or halogen radicals; v is independently selected from integers having a value of from 0 to 4 inclusive; w is independently selected from integers having a value of from 0 to 4 inclusive; and f has a value of at least one, and varies according to the molecular weight of the resin, with the upper-limit of f preferably not exceeding about 10, more preferably not exceeding about 5.
  • R1-R6 are defined hereinafore, and preferably are all
  • Preferred compounds of Formula IX are those wherein R1 - R6 are all hydrogen, and v and w are all zero.
  • An example of commercially available and useful epoxy resins are the EPON resins of Shell Oil Company.
  • those bis-epoxides including the epoxy reins, wherein the two carbon atoms of the oxirane ring ore bonded to three hydrogen atoms, e.g., wherein R1-R6 in Formula V are all hydrogen, are preferred.
  • Preferred bis-epoxides of this type are those wherein the hydrocarbon moieties bridging the epoxide moieties, e.g., R in Formula V, contain polar groups or atoms. These polar groups or atoms include, but are not limited to, the polar hetero atoms or groups described hereinafore.
  • Particularly preferred bis-epoxides are the epoxy resins, especially those devised from polyhydric phenols.
  • the mono- or polyhydric alcohol reactants can comprise at least one member selected from the group consisting of alcohols of the formula: R22(OH) x (X) wherein R22 is a hydrocarbyl group or represents a hydrocarbyl chain, optionally containing one or more hetero chain atoms (e.g., O, S or N), and x is a number of from 1 to 8, e.g., 2 to 5 (preferred).
  • Preferred polyhydric alcohols are polyoxyalkene glycols of the formula: HO-(MO) y (TO) q H (XI) wherein M and T are the same or different and are alkylene groups of at least 2 carbon atoms wherein the sum of y and q is in the range of from 15 to 250, such that the total average molecular weight of the polyoxyalkylene glycol is at least 1,000, preferably from 1,000 to 10,000, more preferably from 2,000 to 8,000.
  • M and T are either 3 or 4 carbon atoms, and therefore preferably the polyoxyalkylene glycol comprises polypropylene glycol, polybutylene glycol or block copolymer mixtures thereof.
  • the selected polyhydric alcohol and bis- epoxide reactants are contacted for reaction in a weight:weight ratio of polyhydric alcohol to bis- epoxide of from 10:1 to 20:1, preferably from 14:1 to 18:1.
  • the reaction for formation of the first adduct may be conducted in the presence of a reaction solvent, such as a hydrocarbon solvent, e.g., toluene, xylene and the like.
  • a reaction solvent such as a hydrocarbon solvent, e.g., toluene, xylene and the like.
  • the quantity of the selected solvent is not critical, although the solvent, e.g., toluene will be usually within the range from 25 to 75 parts of solvent per 100 parts of the first adduct, calculated by weight.
  • the reaction of the selected polyhydric alcohol and bis- epoxide may be conducted in the presence of a small amount of catalyst for the reaction, such as a Lewis base, e.g., caustic soda or caustic potash, which can be employed in the range of from about 0.2 to 0.5 wt.% of all the components charged to the reaction mixture.
  • a Lewis base e.g., caustic soda or caustic potash
  • the desired adduct formed by the reaction of the polyhydric alcohol and bis- epoxide can be illustrated by reference to the following equation, wherein the reaction of polypropylene glycol and the diglycidyl ether of bis-phenol A is illustrated.
  • r1 has the value sufficient to satisfy the number average molecular weight of the polypropylene glycol.
  • r2 will range generally from about 5 to about 120 for polypropylene glycols having number average molecular weights of from about 4000 to about 7000.
  • reaction mass can also contain by-product and unreacted starting material.
  • by-product dimers, trimers and higher "homologues" formed by reactions of molecules of the selected bis- epoxide with the desired polyhydric alcohol.
  • the product mixture obtained from preparation of the first adduct can, if desired, be directly charged to a separate reaction vessel for reaction in the second step with the selected amount of the alkylene oxide, e.g., propylene oxide.
  • the alkylene oxide can be directly introduced into the reaction vessel containing the adduct product mixture.
  • alkylene oxides are ethylene oxide, propylene oxide, 1,2-epoxy butane, 2,3-epoxy butane, 1,2-epoxy pentane, 2,3-epoxy pentane, 1,2-epoxy hexane, 2,3-epoxy hexane, 3,4-epoxy hexane, 1,2-epoxy-3-methyl-butane, and the like.
  • Particularly preferred alkylene oxides are propylene oxide and butylene oxide.
  • the alkylene oxide comprises propylene oxide.
  • the quantity of the alkylene oxide introduced into the second reaction stage for reaction with the adduct can vary widely, but preferably from 0.1 to 20 parts by weight of alkylene oxide, more preferably from 0.4 to 10 parts by weight of alkylene oxide, and most preferably from 1 to 4 parts by weight of alkylene oxide, are reacted with the adduct product mixture per part by weight of the first adduct product mixture.
  • the alkylene oxide charged to this reaction stage will comprise less than about 50 wt.%, still more preferably less than about 40 wt.%, and most preferably less than about 30 wt.% (e.g., 0-20 wt.%), ethylene oxide, with the balance of the charged alkylene oxide comprising propylene oxides and higher epoxides, as described above.
  • the contact of the selected alkylene oxide and the first adduct reaction mixture will be made under conditions for reaction of the alkylene oxide with the hydroxy groups of the first adduct. Conditions effective to achieve such reaction can vary widely, and this second stage reaction will typically employ a reaction temperature within the range of from 110 to 180°C, preferably 130 to 160°C. Any convenient pressure may be used, that is, subatmospheric, atmospheric or superatmospheric, although superatmospheric will be typically preferred.
  • a mixture of alkylene oxides may be employed, e.g., a mixture of ethylene oxide and a higher alkylene oxide (e.g., propylene oxide or butylene oxide).
  • different alkylene oxides can be charged in any sequence, to form "blocks" of the separately charged alkylene oxide.
  • the order of such sequential oxyalkylation, or the number of repeats of any such oxyalkylation, can be varied widely.
  • the first adduct can be oxyethylated, followed by charging of propylene oxide for oxypropylation, or the first adduct can be first treated with propylene oxide followed by oxyethylation of the oxypropylated adduct.
  • propylene or a higher alkylene oxide is preferably charged second (if two alkylation stages are used) or last (in the case of 3 or more alkylation stages), to alkoxylate substantially all of the oxyethylene chain ends.
  • reaction of the selected bis-epoxide and polyhydric alcohol, and the alkoxylation of the resulting adduct are preferably conducted under substantially anhydrous conditions.
  • One of the preferred demulsifiers of this invention can be described as the propoxylated copolymer of a diglycidyl ether of bis-phenol A with polypropylene glycol wherein the polypropylene glycol has a molecular weight of from 2000 to 8000, the weight ratio of the polypropylene glycol to the diglycidyl ether of bis-phenol A is within the range of from 14 to 1 to 18 to 1, and the weight ratio of propylene oxide reacted with the first adduct is within the range of from about 2.5:1 to 3.5:1.
  • the lubricating oil additive mixtures of this invention further comprise a compatibilizing effective amount of at least one alcohol ester or hydroxyamide derivative of a carboxylic acid having a total of from 24 to 90 carbon atoms and at least 1, e.g., about 2 to 3, carboxylic acid groups per molecule.
  • ester compatibility additives are derived from the esterification of a monocarboxylic or polycarboxylic acid with a mono-, di- or trihydric alcohol (e.g., glycol, glycerol, oxa-alkane diols).
  • esters have been heretofore used in lubricating oils as friction modifiers, and the methods of preparation thereof, and structures, are described in US-A-3,429,817; 4,459,223; 4,479,883; 4,617,026; and 4,683,069.
  • the hydroxyamide derivatives of such mono- and polycarboxylic acids can be prepared by condensing the acid at elevated temperature with a hydroxyamine (e.g. alkanol amines or aminoalochols, such as ethanolamine, diethanol-amine, propanolamine, 3-amino-1,1-propanediol), employing the methods disclosed in US-A-4,557,846.
  • a hydroxyamine e.g. alkanol amines or aminoalochols, such as ethanolamine, diethanol-amine, propanolamine, 3-amino-1,1-propanediol
  • the carboxylic acid may be an aliphatic saturated or unsaturated acid and will generally have a total of 24 to 90, preferably 24 to 60, carbon atoms and at least 1, e.g., 2 to 3, preferably about 2, carboxylic acid groups with at least about 9 carbon atoms, preferably 12 to 42, especially 16 to 22 carbon atoms between the carboxylic acid groups.
  • hydroxyamide compatibilizers are oil soluble hydroxyamide compounds having the formula: wherein J1 is the hydrocarbon radical or skeleton of a dimer carboxylic acid having a total of 24 to 90 carbon atoms with 9 to 42 carbon atoms between carboxylic acid groups; Z is (a) a hydroxy substituted alkyl group having 1 to 20 carbon atoms, or (b) an oxyalkylene group of the formula: where A and E are each alkyl of 1 to 2 carbon atoms or hydrogen and n7 is an integer of 1 to 50; n4 is 0 or 1; n5 is 1 or 2 and n6 is 1 or 2.
  • Preferred compatibilizers comprise partial esters or diesters of dicarboxylic acids of the formulas: HO-J'-OOC-J-COOH (XIIIa), and HO-J'-OOC-J-COOJ''-OH (XIIIb) wherein J is the hydrocarbon radical of the acid and J' and J'' is either the hydrocarbon radical of an alkane diol or the oxy-alkylene radical from an oxa-alkane diol as defined hereinbelow. Generally 1-3 moles of glycol, preferably 1-2 moles of glycol, are used per mole of acid to provide either a complete or partial ester.
  • esters can be obtained by esterifying a mono- or dicarboxylic acid or mixture of such acids with a mixture of diols, in which case J would then be the hydrocarbon radical of the dicarboxylic acid(s) and J' and J'' would be the hydrocarbon radicals associated with the diols.
  • the compatibility additives are used in amounts ranging from 0.1 to 5 parts by weight, more preferably 0.5 to 1.5 parts by weight based upon the weight of the Component B demulsifier additive in the lubricating oil composition. If desired, higher amounts of the compatability additive may be employed, since such polycarboxylic acid-glycol esters may also serve as friction modifiers in the lubricating oil composition. Therefore, the compatability additives will be generally employed in an amount of from 0.0005 to 2, more preferably from 0.001 to 0.25, and most preferably from 0.005 to 0.1, weight percent.
  • dimer acid esters are particularly preferred compatibilizer additives.
  • dimer acid used herein is meant to refer to those substituted cyclohexene dicarboxylic acids formed by a Diels-Alder-type reaction (which is a thermal condensation) of C18-C22 unsaturated fatty acids, such as tall oil fatty acids, which typically contain 85 to 90 percent oleic or linoleic acids.
  • Such dimer acids typically contain 36 carbon atoms.
  • the dimer acid structure can be generalized as follows: with two of the R23-R26 groups containing carboxyl groups and two being hydrocarbon groups depending upon how the condensation of the carboxylic acid has occurred.
  • dimer of linoleic acid which is the preferred embodiment can be expressed in the following formula: Also the term dimer acid as used herein necessarily includes products containing trimers (and higher homologues), e.g., up to about 24 percent by weight trimer, but more typically about 10 percent by weight trimer since, as is well known in the art, the dimerization reaction provides a product containing a trimer acid having molecular weight of about three times the molecular weight to the starting fatty acid.
  • the polycarboxylic acids or dimer acids noted above are esterified with a glycol, the glycol being an alkane diol or oxa-alkane diol represented by the formula HO(R27CHCH2O) x1 H wherein R27 is H or CH3 and x1 is 1 to 100, preferably 1 to 25 with ethylene glycol and diethylene glycol particularly preferred.
  • a preferred embodiment is formation of the ester with 1 to 2 moles of glycol per mole of dimer acid or polycarboxylic acid, such as the ester of diethylene glycol with dimerized linoleic acid.
  • Illustrative of such esters are compounds of the formula (XVI): wherein D is x1 is as defined above.
  • the lubricating oil metal detergent additives are also frequently referred to as rust inhibitors and include the magnisum or calcium or barium salts of sulphonic acids, alkyl phenols, sulphurized alkyl phenols, alkyl salicylates and naphthenates. Highly basic, that is overbased metal salts, are frequently used as detergents and appear particularly prone to interaction with the ashless dispersant.
  • these metal containing rust inhibitors and detergents are used in lubricating oil in amounts of 0.01 to 10, e.g. 0.1 to 5 wt. %, based on the weight of the total lubricating composition.
  • Marine diesel lubricating oils typically employ such metal-containing rust inhibitors and detergents in amounts of up to about 20 wt.%.
  • Highly basic alkaline earth metal sulfonates are frequently used as detergents. They are usually produced by heating a mixture comprising an oil-soluble sulfonate or alkaryl sulfonic acid, with an excess of alkaline earth metal compound above that required for complete neutralization of any sulfonic acid present and thereafter forming a dispersed carbonate complex by reacting the excess metal with carbon dioxide to provide the desired overbasing.
  • the sulfonic acids are typically obtained by the sulfonation of alkyl substituted aromatic hydrocarbons such as those obtained from the fractionation of petroleum by distillation and/or extraction or by the alkylation of aromatic hydrocarbons as for example those obtained by alkylating benzene, toluene, xylene, naphthalene, diphenyl and the halogen derivatives such as chlorobenzene, chlorotoluene and chloronaphthalene.
  • the alkylation may be carried out in the presence of a catalyst with alkylating agents having from 3 to more than 30 carbon atoms.
  • the alkaline earth metal compounds which may be used in neutralizing these alkaryl sulfonic acids to provide the sulfonates includes the oxides and hydroxides, alkoxides, carbonates, carboxylate, sulfide, hydrosulfide, nitrate, borates and ethers of magnesium, calcium, and barium. Examples are calcium oxide, calcium hydroxide, magnesium acetate and magnesium borate.
  • the alkaline earth metal compound is used in excess of that required to complete neutralization of the alkaryl sulfonic acids. Generally, the amount ranges from about 100 to 220%, although it is preferred to use at least 125%, of the stoichiometric amount of metal required for complete neutralization.
  • a preferred alkaline earth sulfonate additive is magnesium alkyl aromatic sulfonate having a total base number ASTM D2896 ranging from 300 to 400 with the magnesium sulfonate content ranging from 25 to 32 wt. %, based upon the total weight of the additive system dispersed in mineral lubricating oil.
  • Neutral metal sulfonates are frequently used as rust inhibitors.
  • Polyvalent metal alkyl salicylate and naphthenate materials are known additives for lubricating oil compositions to improve their high temperature performance and to counteract deposition of carbonaceous matter on pistons (US-A-2,744,069).
  • An increase in reserve basicity of the polyvalent metal alkyl salicylates and naphthenates can be realized by utilizing alkaline earth metal, e.g.
  • polyvalent metal salicylate and naphthenate materials include the methylene and sulfur bridged materials which are readily derived from alkyl substituted salicylic or naphthenic acids or mixtures of either or both with alkyl substituted phenols.
  • Basic sulfurized salicylates and a method for their preparation is shown in US-A-3,595,791.
  • Such materials include alkaline earth metal, particularly magnesium, calcium, strontium and barium salts of aromatic acids having the general formula: HOOC-ArR1-Xy(ArR10H) n (XVII) where Ar is an aryl radical of 1 to 6 rings, R1 is an alkyl group having from 8 to 50 carbon atoms, preferably 12 to 30 carbon atoms (optimally about 12), X is a sulfur (-S-) or methylene (-CH2-) bridge, y is a number from 0 to 4 and n is a number from 0 to 4.
  • overbased methylene bridged salicylate-phenate salt is readily carried out by conventional techniques such as by alkylation of a phenol followed by phenation, carboxylation, hydrolysis, methylene bridging a coupling agent such as an alkylene dihalide followed by salt formation concurrent with carbonation.
  • An overbased calcium salt of a methylene bridged phenol-salicylic acid of the general formula (XVIII): with a TBN of 60 to 150 is highly useful in this invention.
  • the individual R28 groups may each contain from 5 to 40, preferably 8 to 20, carbon atoms.
  • the metal salt is prepared by reacting an alkyl phenol sulfide with a sufficient quantity of metal containing material to impart the desired alkalinity to the sulfurized metal phenate.
  • the sulfurized alkyl phenols which are useful generally contain from 2 to 14% by weight, preferably 4 to 12 wt. % sulfur based on the weight of sulfurized alkyl phenol.
  • the sulfurized alkyl phenol may be converted by reaction with a metal containing material including oxides, hydroxides and complexes in an amount sufficient to neutralize said phenol and, if desired, to overbase the product to a desired alkalinity by procedures well known in the art.
  • a metal containing material including oxides, hydroxides and complexes in an amount sufficient to neutralize said phenol and, if desired, to overbase the product to a desired alkalinity by procedures well known in the art.
  • Preferred is a process of neutralization utilizing a solution of metal in a glycol ether.
  • the lubricating oil additive mixtures of the present invention can be incorporated into a lubricating oil in any convenient way.
  • these mixtures can be added directly to the oil by dispersing or dissolving the same in the oil at the desired level of concentrations of the ashless dispersant, demulsifier, compatibility additive, and metal detergent (where employed), respectively.
  • Such blending into the additional lube oil can occur at room temperature or elevated temperatures.
  • the ashless dispersant, demulsifier, compatibility additive, and metal detergent (where employed) can be blended with a suitable oil-soluble solvent or base oil to form a concentrate, and which can then be blended with a lubricating oil basestock to obtain the final formulation.
  • Such concentrates will typically contain (on an active ingredient (A.I.) basis) from 3 to 45 wt. %, and preferably from 10 to 35 wt. %, ashless dispersant additive A; typically from 0.01 to 3 wt.%, and preferably from 0.05 to 0.3 wt.% demulsifier additive B; (where present) typically from 0.0005 to 2 wt.%, preferably from 0.001 to 0.25 wt.%, and most preferably from 0.005 to 0.1 wt.% compatibility additive C; (where present) typically from 2 to 45 wt.%, and preferably from 2 to 14 wt.%, metal detergent D; and typically from 30 to 90 wt. %, preferably from 40 to 60 wt. %, base oil, based on the concentrate weight.
  • A.I. active ingredient
  • demulsifier additive B typically from 0.01 to 3 wt.%, and preferably from 0.05 to 0.3 wt.% demulsifier additive
  • Additive packages i.e. concentrates of this invention comprising ashless dispersant, metal detergent, demulsifier and compatibility additive (alone or together with other lubricating oil additives as discussed below, e.g., antiwear additives, corrosion inhibitors, antioxidants, etc.) are preferably prepared in the following manner.
  • the ashless dispersant and metal detergent components (in the selected baseoil or solvent) are preferably first blended together at elevated temperature (e.g., from 70 to 130°C) for a time and under stirring sufficient to intimately contact these components, followed by cooling of the dispersant/detergent mixture to 65°C or below, as disclosed in co-pending EP-A-0294-096.
  • the selected demulsifier and compatibility additive are separately admixed in the selected baseoil or solvent for a time and under conditions sufficient to intimately contact these components (e.g., from 50 to 130°C, for 1 to 5 hours, with stirring), and then introduced as a mixture to the dispersant/detergent mixture, e.g., at 50 to 130°C with stirring to provide intimate blending, for 1 to 5 hours.
  • the remaining lubricating oil additives can be added (separately or simultaneously) prior to, during or after the mixing of the dispersant/detergent mixture with the demulsifier/compatibility additive mixture.
  • the lubricating oil basestock for the lubricating oil mixture typically is adapted to perform a selected function by the incorporation of additional additives therein to form lubricating oil compositions (i.e., formulations).
  • the additive mixtures of the present invention possess very good demulsifying properties as measured herein in a wide variety of environments. Accordingly, the additive mixtures are used by incorporation and dissolution into an oleaginous material such as fuels and lubricating oils.
  • an oleaginous material such as fuels and lubricating oils.
  • a concentration of the additives in the fuel in the range of typically from 0.001 to 0.5, and preferably 0.005 to 0.15 weight percent, based on the total weight of the composition, will usually be employed.
  • the additive mixtures of the present invention find their primary utility in lubricating oil compositions which employ a base oil in which the additives are dissolved or dispersed.
  • base oils may be natural or synthetic.
  • Base oils suitable for use in preparing the lubricating oil compositions of the present invention include those conventionally employed as crankcase lubricating oils for spark-ignited and compression-ignited internal combustion engines, such as automobile and truck engines, marine and railroad diesel engines, and the like.
  • Advantageous results are also achieved by employing the additive mixtures of the present invention in base oils conventionally employed in and/or adapted for use as power transmitting fluids such as automatic transmission fluids, tractor fluids, universal tractor fluids and hydraulic fluids, heavy duty hydraulic fluids, power steering fluids and the like.
  • Gear lubricants, industrial oils, pump oils and other lubricating oil compositions can also benefit from the incorporation therein of the additive mixtures of the present invention.
  • lubricating oil formulations conventionally contain several different types of additives that will supply the characteristics that are required in the formulations.
  • additives include viscosity index improvers, antioxidants, corrosion inhibitors, detergents, dispersants, pour point depressants, antiwear agents, friction modifiers, etc.
  • the additives in the form of 10 to 80 wt. %, e.g., 20 to 80 wt. % active ingredient concentrates in hydrocarbon oil, e.g. mineral lubricating oil, or other suitable solvent.
  • hydrocarbon oil e.g. mineral lubricating oil, or other suitable solvent.
  • these concentrates may be diluted with 3 to 100, e.g. 5 to 40 parts by weight of lubricating oil, per part by weight of the additive package, in forming finished lubricants, e.g. crankcase motor oils.
  • the purpose of concentrates is to make the handling of the various materials less difficult and awkward as well as to facilitate solution or dispersion in the final blend.
  • a metal hydrocarbyl sulfonate or a metal alkyl phenate would be usually employed in the form of a 40 to 50 wt. % concentrate, for example, in a lubricating oil fraction.
  • the ashless dispersant and demulsifier mixtures of the present invention will be generally used in admixture with a lube oil basestock, comprising an oil of lubricating viscosity, including natural and synthetic lubricating oils and mixtures thereof.
  • Natural base oils include animal oils and vegetable oils (e.g., castor, lard oil) liquid petroleum oils and hydrorefined, solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale are also useful base oils.
  • animal oils and vegetable oils e.g., castor, lard oil
  • mineral lubricating oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types.
  • Oils of lubricating viscosity derived from coal or shale are also useful base oils.
  • 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 polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methyl-poly isopropylene glycol ether having an average molecular weight of 1000, diphenyl ether of poly-ethylene glycol having a molecular weight of 500-1000, diethyl ether of polypropylene glycol having a molecular weight of 1000-1500); and mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C3-C8 fatty acid esters and C13 Oxo acid diester of tetraethylene glycol.
  • polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide
  • 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, sebasic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkylmalonic acids, alkenyl malonic acids) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic acid, linole
  • esters include dibutyl adipate, 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, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
  • Esters useful as synthetic oils also include those made from C5 to C12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol.
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxysiloxane oils and silicate oils comprise another useful class of synthetic lubricants; they include 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 and poly(methylphenyl)siloxanes.
  • Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid) and polymeric tetrahydrofurans.
  • Unrefined, refined and rerefined oils can be used in the lubricants of the present invention.
  • 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, such as distillation, solvent extraction, acid or base extraction, filtration and percolation are known to those skilled in the art.
  • 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 for removal of spent additives and oil breakdown products.
  • the ashless dispersant demulsifier mixtures of the present invention can also be used with V.I improvers to form multi-grade automobile engine lubricating oil formulations.
  • Viscosity modifiers impart high and low temperature operability to the lubricating oil and permit it to remain relatively viscous at elevated temperatures and also exhibit acceptable viscosity or fluidity at low temperatures.
  • Viscosity modifiers are generally high molecular weight hydrocarbon polymers including polyesters.
  • the viscosity modifiers may also be derivatized to include other properties or functions, such as the addition of dispersancy properties.
  • oil soluble viscosity modifying polymers will generally have number average molecular weights of from 103 to 106, preferably 104 to 106, e.g., 20,000 to 250,000, as determined by gel permeation chromatography or osmometry.
  • suitable hydrocarbon polymers include homopolymers and copolymers of two or more monomers of C2 to C30, e.g. C2 to C8 olefins, including both alpha olefins and internal olefins, which may be straight or branched, aliphatic, aromatic, alkyl-aromatic, cycloaliphatic, etc. Frequently they will be of ethylene with C3 to C30 olefins, particularly preferred being the copolymers of ethylene and propylene.
  • polystyrene e.g. with isoprene and/or butadiene and hydrogenated derivatives thereof.
  • the polymer may be degraded in molecular weight, for example by mastication, extrusion, oxidation or thermal degradation, and it may be oxidized and contain oxygen.
  • the preferred hydrocarbon polymers are ethylene copolymers containing from 15 to 90 wt. % ethylene, preferably 30 to 80 wt. % of ethylene and 10 to 85 wt. %, preferably 20 to 70 wt. % of one or more C3 to C28, preferably C3 to C18, more preferably C3 to C8, alpha-olefins. While not essential, such copolymers preferably have a degree of crystallinity of less than 25 wt. %, as determined by X-ray and differential scanning calorimetry. Copolymers of ethylene and propylene are most preferred.
  • Terpolymers, tetrapolymers, etc., of ethylene, said C3 ⁇ 28 alpha-olefin, and a non-conjugated diolefin or mixtures of such diolefins may also be used.
  • the amount of the non-conjugated diolefin generally ranges from about 0.5 to 20 mole percent, preferably from about 1 to about 7 mole percent, based on the total amount of ethylene and alpha-olefin present.
  • the polyester V.I. improvers are generally polymers of esters of ethylenically unsaturated C3 to C8 mono- and dicarboxylic acids such as methacrylic and acrylic acids, maleic acid, maleic anhydride, fumaric acid.
  • unsaturated esters examples include those of aliphatic saturated mono alcohols of at least 1 carbon atom and preferably of from 12 to 20 carbon atoms, such as decyl acrylate, lauryl acrylate, stearyl acrylate, eicosanyl acrylate, docosanyl acrylate, decyl methacrylate, diamyl fumarate, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate, and the like and mixtures thereof.
  • esters include the vinyl alcohol esters of C2 to C22 fatty or mono carboxylic acids, preferably saturated such as vinyl acetate, vinyl laurate, vinyl palmitate, vinyl stearate, vinyl oleate, and the like and mixtures thereof. Copolymers of vinyl alcohol esters with unsaturated acid esters such as the copolymer of vinyl acetate with dialkyl fumarates, can also be used.
  • the esters may be copolymerized with still other unsaturated monomers such as olefins, e.g. 0.2 to 5 moles of C2 - C20 aliphatic or aromatic olefin per mole of unsaturated ester, or per mole of unsaturated acid or anhydride followed by esterification.
  • unsaturated monomers such as olefins, e.g. 0.2 to 5 moles of C2 - C20 aliphatic or aromatic olefin per mole of unsaturated ester, or per mole of unsaturated acid or anhydride followed by esterification.
  • olefins e.g. 0.2 to 5 moles of C2 - C20 aliphatic or aromatic olefin per mole of unsaturated ester, or per mole of unsaturated acid or anhydride followed by esterification.
  • Dihydrocarbyl dithiophosphate metal salts are frequently used as anti-wear agents and also provide antioxidant activity.
  • the zinc salts are most commonly used in lubricating oil in amounts of 0.1 to 10, preferably 0.2 to 2 wt. %, based upon the total weight of the lubricating oil composition. They may be prepared in accordance with known techniques by first forming a dithiophosphoric acid, usually by reaction of an alcohol or a phenol with P2S5 and then neutralizing the dithiophosphoric acid with a suitable zinc compound.
  • Mixtures of alcohols may be used including mixtures of primary and secondary alcohols, secondary generally for imparting improved anti-wear properties, with primary giving improved thermal stability properties. Mixtures of the two are particularly useful.
  • any basic or neutral zinc compound could be used but the oxides, hydroxides and carbonates are most generally employed.
  • Commercial additives frequently contain an excess of zinc due to use of an excess of the basic zinc compound in the neutralization reaction.
  • the zinc dihydrocarbyl dithiophosphates useful in the present invention are oil soluble salts of dihydrocarbyl esters of dithiophosphoric acids and may be represented by the following formula: wherein R29 and R30 may be the same or different hydrocarbyl radicals containing from 1 to 18, preferably 2 to 12 carbon atoms and including radicals such as alkyl, alkenyl, aryl, aralkyl, alkaryl and cycloaliphatic radicals. Particularly preferred as R29 and R30 groups are alkyl groups of 2 to 8 carbon atoms.
  • the radicals may, for example, be ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, amyl, n-hexyl, i-hexyl, n-octyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, phenyl, butylphenyl, cyclohexyl, methylcyclopentyl, propenyl, butenyl etc.
  • the total number of carbon atoms (i.e. R29 and R30 in formula XX) in the dithiophosphoric acid will generally be about 5 or greater.
  • the antioxidants useful in this invention include copper compounds.
  • a copper compound may be blended into the oil (e.g., an an oil soluble copper compound) to provide copper in an oil-solubilized form.
  • oil soluble we mean the compound is oil soluble under normal blending conditions in the oil or additive package.
  • the copper compound may be in the cuprous or cupric form.
  • the copper may be in the form of the copper dihydrocarbyl thio- or dithio-phosphates wherein copper may be substituted for zinc in the compounds and reactions described above although one mole of cuprous or cupric oxide may be reacted with one or two moles of the dithiophosphoric acid, respectively.
  • the copper may be added as the copper salt of a synthetic or natural carboxylic acid.
  • R31 and R32 groups are alkyl groups of 2 to 8 carbon atoms.
  • the radicals may, for example, be ethyl, n-propyl, i-propyl, n-butyl,-i-butyl, sec-butyl, amyl, n-hexyl, i-hexyl, n-heptyl, n-octyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, phenyl, butylphenyl, cyclohexyl, methylcyclopentyl, propenyl, butenyl, etc.
  • the total number of carbon atoms i.e, R31 and R32
  • Copper sulphonates, phenates, and acetylacetonates may also be used.
  • Examples of the metal salts of this invention are Cu salts of polyisobutenyl succinic anhydride (hereinafter referred to as Cu-PIBSA), and Cu salts of polyisobutenyl succinic acid.
  • the selected metal employed is its divalent form, e.g., Cu+2.
  • the preferred substrates are polyalkenyl succinic acids in which the alkenyl group has a molecular weight greater than about 700.
  • the alkenyl group desirably has a M n from 900 to 1400, and up to 2500, with a M n of about 950 being most preferred.
  • PIBSA polyisobutylene succinic acid
  • These materials may desirably be dissolved in a solvent, such as a mineral oil, and heated in the presence of a water solution (or slurry) of the metal bearing material. Heating may take place between 70° and 200°C. Temperatures of 110° to 140°C are entirely adequate. It may be necessary, depending upon the salt produced, not to allow the reaction to remain at a temperature above about 140°C for an extended period of time, e.g., longer than 5 hours, or decomposition of the salt may occur.
  • a solvent such as a mineral oil
  • the copper antioxidants (e.g., Cu-PIBSA, Cu-oleate, or mixtures thereof) will be generally employed in an amount of from 50-500 ppm by weight of the metal, in the final lubricating or fuel composition.
  • the copper antioxidants used in this invention are inexpensive and are effective at low concentrations and therefore do not add substantially to the cost of the product. The results obtained are frequently better than those obtained with previously used antioxidants, which are expensive and used in higher concentrations. In the amounts employed, the copper compounds do not interfere with the performance of other components of the lubricating composition, in many instances, completely satisfactory results are obtained when the copper compound is the sole antioxidant in addition to the ZDDP.
  • the copper compounds can be utilized to replace part or all of the need for supplementary antioxidants. Thus, for particularly severe conditions it may be desirable to include a supplementary, conventional antioxidant. However, the amounts of supplementary antioxidant required are small, far less than the amount required in the absence of the copper compound.
  • Corrosion inhibitors also known as anti-corrosive agents, reduce the degradation of the metallic parts contacted by the lubricating oil composition.
  • Illustrative of corrosion inhibitors are phosphosulfurized hydrocarbons and the products obtained by reaction of a phosphosulfurized hydrocarbon with an alkaline earth metal oxide or hydroxide, preferably in the presence of an alkylated phenol or of an alkylphenol thioester, and also preferably in the presence of carbon dioxide.
  • Phosphosulfurized hydrocarbons are prepared by reacting a suitable hydrocarbon such as a terpene, a heavy petroleum fraction of a C2 to C6 olefin polymer such as polyisobutylene, with from 5 to 30 weight percent of a sulfide of phosphorus for 1/2 to 15 hours, at a temperature in the range of 65° to 315°C. Neutralization of the phosphosulfurized hydrocarbon may be effected in the manner taught in US-A-1,969,324.
  • Oxidation inhibitors reduce the tendency of mineral oils to deteriorate in service which deterioration can be evidenced by the products of oxidation such as sludge and varnish-like deposits on the metal surfaces and by viscosity growth.
  • oxidation inhibitors include alkaline earth metal salts of alkylphenolthioesters having preferably C5 to C12 alkyl side chains, calcium nonylphenol sulfide, barium t-octylphenyl sulfide, dioctylphenylamine, phenylalphanaphthylamine, phosphosulfurized or sulfurized hydrocarbons.
  • Friction modifiers serve to impart the proper friction characteristics to lubricating oil compositions such as automatic transmission fluids.
  • the most preferred friction modifiers are glycerol mono and dioleates, and succinate esters, or metal salts thereof, of hydrocarbyl substituted succinic acids or anhydrides and thiobis-alkanols such as described in US-A-4,344,853.
  • Foam control can be provided by an antifoamant of the polysiloxane type, e.g. silicone oil and polydimethyl siloxane.
  • an antifoamant of the polysiloxane type e.g. silicone oil and polydimethyl siloxane.
  • Organic, oil-soluble compounds useful as rust inhibitors in this invention comprise nonionic surfactants such as polyoxyalkylene polyols and esters thereof, and anionic surfactants such as salts of alkyl sulfonic acids.
  • nonionic surfactants such as polyoxyalkylene polyols and esters thereof
  • anionic surfactants such as salts of alkyl sulfonic acids.
  • Such anti-rust compounds are known and can be made by conventional means.
  • Nonionic surfactants, useful as anti-rust additives in the oleaginous compositions of this invention usually owe their surfactant properties to a number of weak stabilizing groups such as ether linkages.
  • Nonionic anti-rust agents containing ether linkages can be made by alkoxylating organic substrates containing active hydrogens with an excess of the lower alkylene oxides (such as ethylene and propylene oxides) until the desired number of alkoxy groups have been placed in the molecule.
  • the lower alkylene oxides such as ethylene and propylene oxides
  • the preferred rust inhibitors are polyoxyalkylene polyols and derivatives thereof. This class of materials are commercially available from various sources: Pluronic Polyols from Wyandotte Chemicals Corporation; Polyglycol 112-2, a liquid triol derived from ethylene oxide and propylene oxide available from Dow Chemical Co.; and Tergitol, dodecylphenyl or monophenyl polyethylene glycol ethers, and Ucon, polyalkylene glycols and derivatives, both available from Union Carbide Corp. These are but a few of the commercial products suitable as rust inhibitors in the improved composition of the present invention.
  • esters thereof obtained by reacting the polyols with various carboylic acids are also suitable.
  • Acids useful in preparing these esters are lauric acid, stearic acid, succinic acid, and alkyl- or alkenyl-substituted succinic acids wherein the alkyl-or alkenyl group contains up to about twenty carbon atoms.
  • the hydrophobic portion can be increased and/or the hydrophilic portion decreased. If greater oil-in-water emulsion breaking ability is required, the hydrophilic and/or hydrophobic portions can be adjusted to accomplish this.
  • Q-(OH)n8 examples include alkylene polyols such as the alkylene glycols, alkylene triols, alkylene tetrols, etc., such as ethylene glycol, propylene glycol, glycerol, pentaerythritol, sorbitol, mannitol, and the like.
  • alkylene polyols such as the alkylene glycols, alkylene triols, alkylene tetrols, etc., such as ethylene glycol, propylene glycol, glycerol, pentaerythritol, sorbitol, mannitol, and the like.
  • Aromatic hydroxy compounds such as alkylated mono- and polyhydric phenols and naphthols can also be used, e.g., heptylphenol, dodecylphenol.
  • demulsifiers include the esters disclosed in US-A-3,098,827 and 2,674,619.
  • the liquid polyols available from Wyandotte Chemical Co. under the name Pluronic Polyols and other similar polyols are particularly well suited as rust inhibitors.
  • Pluronic Polyols correspond to the formula: wherein z, z' and z'' are integers greater than 1 such that the -CH2CH2O- groups comprise from 10% to 40% by weight of the total molecular weight of the glycol, the average molecule weight of said glycol being from 1000 to 5000.
  • These products are prepared by first condensing propylene oxide with propylene glycol to produce the hydrophobic base This condensation product is then treated with ethylene oxide to add hydrophilic portions to both ends of the molecule.
  • the ethylene oxide units should comprise from 10 to 40% by weight of the molecule.
  • Those products wherein the molecular weight of the polyol is from 2500 to 4500 and the ethylene oxide units comprise from 10% to 15% by weight of the molecule are particularly suitable.
  • the polyols having a molecular weight of 4000 with about 10% attributable to (CH2CH2O) units are particularly good.
  • alkoxylated fatty amines, amides, alcohols and the like including such alkoxylated fatty acid derivatives treated with C9 to C16 alkyl-substituted phenols (such as the mono- and di-heptyl, octyl, nonyl, decyl, undecyl, dodecyl and tridecyl phenols), as described in US-A-3,849,501.
  • the lubricating composition of the present invention may also include copper lead bearing corrosion inhibitors.
  • such compounds are the thiadiazole polysulphides containing from 5 to 50 carbon atoms, their derivatives and polymers thereof.
  • Preferred materials are the derivatives of 1,3,4 thiadiazoles such as those described in US-A-2,719,125; 2,719,126; and 3,087,932; especially preferred is the compound 2,5 bis (t-octadithio)-1,3,4 thiadiazole commercially available as Amoco 150.
  • Other similar materials also suitable are described in US-A-3,821,236; 3,904,537; 4,097,387; 4,107,059; 4,136,043; 4,188,299; and 4,193,882.
  • Suitable additives are the thio and polythio sulphenamides of thiadiazoles such as those described in GB-A-1,560,830.
  • these compounds when included in the lubricating composition, we prefer that they be present in an amount from 0.01 to 10, preferably 0.1 to 5.0 weight percent based on the weight of the composition.
  • compositions when containing these conventional additives are typically blended into the base oil in amounts effective to provide their normal attendant function.
  • Representative effective amounts of such additives (as the respective active ingredients) in the fully formulated oil are illustrated as follows: Compositions Wt.% A.I. (Preferred) Wt.% A.I.
  • additive concentrates comprising concentrated solutions or dispersions of the novel ashless dispersant/demulsifier mixtures of this invention (in concentrate amounts hereinabove described), together with one or more of said other additives (including metal detergent, compatabilizer, etc.) (said concentrate when constituting an additive mixture being referred to herein as an additive-package) whereby several additives can be added simultaneously to the base oil to form the lubricating oil composition or formulation. Dissolution of the additive concentrate into the lubricating oil may be facilitated by solvents and by mixing accompanied with mild heating, but this is not essential.
  • the concentrate or additive-package will typically be formulated to contain the additives in proper amounts to provide the desired concentration in the final formulation when the additive-package is combined with a predetermined amount of base lubricant.
  • the mixtures of the present invention can be added to small amounts of base oil or other compatible solvents along with other desirable additives to form additive-packages containing active ingredients in collective amounts of typically from 2.5 to 90%, and preferably from 15 to 75%, and most preferably from 25 to 60% by weight additives in the appropriate proportions with the remainder being base oil.
  • the final formulations may employ typically about 10 wt. % of the additive-package with the remainder being base oil.
  • test lubricating oil formulations are prepared containing ashless dispersant, metal detergent, viscosity modifier and the demulsifiers of this invention, or other test materials, identified in Tables I and II below.
  • the indicated compositions were tested in a shortened version of the Sequence IID test (referred to as the IID Screener) in which the ASTM Sequence IID procedure is followed for 12 hours using an Oldsmobile V8 engine which is not rebuilt but is instead carefully flushed between runs. Crankcase pressure is monitored for the 12 hours to produce an integrated (cumulative) crankcase pressure value.
  • the data thereby obtained are summarized in Table III.
  • the pressure data in Table III indicate the surprisingly reduced crankcase pressure resulting from the use of the demulsifiers of this invention in Examples 4-11 as compared to the polypropylene glycol and polypropylene glycol/diglycidyl ether adduct in Comparative Examples A and B, respectively, and as compared to the much higher crankcase pressure generated by the control, non-demulsified control (Comparative Example C).
  • the propoxylated demulsifiers of Examples 1 - 2 provided particularly reduced crankcase pressure, and were superior in this respect to the demulsifier of Example 3 which contained equal weights of oxyalkylene units derived from ethylene oxide and propylene oxide.
  • Comparative B illustrates the criticality to the alkoxylation step in preparing the demulsifiers of this invention.
  • Diethylene glycol ester of dimer and trimer of linoleic acid Diethylene glycol ester of dimer and trimer of linoleic acid.
  • Solvent about 150 neutral mineral oil base oil, also containing copper antioxidant, zinc dialkyldithiophosphate antiwear agent, ethylene propylene copolymer viscosity index improver and supplemental nonylphenol sulfide antioxidant.
  • Table V illustrate the improved additive package stability observed in use of the demulsifiers and compatibility additives of this invention. Substantial improvements in reduced haze were achieved when the propoxylated demulsifier of Example 2, wherein a propylene oxide:adduct weight:weight ratio of 0.6:1 was employed, in combination with a compatibility additive of this invention. Whereas haze was observed after 5 days in Example 12, no haze appeared in the additive package of Example 13 even after 96 days of storage at 66°C.
  • an ashless dispersant polyisobutennyl succinimide of a polyethylene polyamine having about 7 carbon atoms and 5 to 6 nitrogen atoms per polyamine molecule
  • each blend is cooled to 75°C, and then the following additional components are introduced, with the indicated components beings used in the same concentrations in each blend: zinc dialkyl dithiophosphate antiwear agent, nonyl phenol sulfide oxidation inhibitor, and copper antioxidant, to form a partial adpack (95.3 parts).
  • each partial addpack (at 75°C) is introduced the selected amount of demulsifier and compatability additives of this invention, together with sufficient lubricating oil to make up the balance of 100 parts of the weight of the lubricating oil concentrate.
  • the order of mixing these additional components is varied as follows:
  • Example 2 propoxylated adduct of polypropylene glycol and diglycidyl ether of bis-phenol A.
  • the above data illustrate the improved storage stability achieved by the premixing of the demulsifiers and compatibility additives of this invention prior to contacting the demulsifier with the remaining components of the additive package, as compared to the use of equivalent amounts of the demulsifier and compatibility additive without such premixing.
  • the storage stability achieved by the premixing of the demulsifier with the linoleic acid dimer glycol ester additive in Example 22 is particularly surprising in view of the art's recognition of the instability problems heretofore observed in use of such esters as friction modifiers as discussed above.

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Claims (23)

  1. Mélange soluble dans l'huile, utile comme additif d'huile, comprenant :
    (A) un additif sans cendre pour huile lubrifiante, comprenant
    (1) des dispersants sans cendre choisis entre : (i) des sels d'amines, des amides, des imides, des oxazolines et des esters solubles dans l'huile, ou leurs mélanges, d'une matière du type acide, c'est-à-dire un acide, un anhydride ou un ester, mono- ou dicarboxylique à substituant hydrocarboné à chaîne longue ; (ii) un groupe hydrocarboné aliphatique à chaîne longue possédant une polyamine fixée directement à ce groupe ; et (iii) des produits de condensation de Mannich formés par condensation d'approximativement une proportion molaire d'un phénol à substituant hydrocarboné à chaîne longue avec 1 à 2,5 moles de formaldéhyde et 0,5 à 2 moles d'une polyalkylènepolyamine ; ledit groupe hydrocarboné à chaîne longue dans (i), (ii) ou (iii) étant un polymère d'une mono-oléfine en C₂ à C₁₀, ledit polymère ayant une moyenne numérique du poids moléculaire d'au moins 900 ;
    (2) des dispersants-améliorants d'indice de viscosité polymériques choisis entre : (i) des polymères constitués d'esters insaturés en C₄ à C₂₄ d'alcool vinylique ou d'un acide mono- ou dicarboxylique insaturé en C₃ à C₁₀ avec des monomères azotés insaturés ayant 4 à 20 atomes de carbone ; (ii) des polymères d'une oléfine en c₂ à c₂₀ avec un acide mono- ou dicarboxylique insaturé en C₃ à C₁₀ neutralisé avec une amine, une hydroxyamine ou des alcools ; et (iii) des polymères d'éthylène avec une oléfine en C₃ à C₂₀, soumis à une réaction supplémentaire par greffage de monomères azotés insaturés en C₄ à C₂₀ sur ces polymères ou par greffage d'un acide insaturé sur le squelette du polymère, puis réaction desdits groupes acide carboxylique avec une amine, une hydroxyamine ou un alcool ; et des mélanges de (A)(1) et (A)(2) ; et
    (B) un additif désémulsionnant,
       caractérisé en ce que ledit additif désémulsionnant (B) comprend le produit de réaction
    (i) d'un oxyde d'alkylène ayant 2 à 10 atomes de carbone, et
    (ii) d'un produit d'addition obtenu par réaction d'un alcool polyhydroxylique avec un bis-époxyde contenant au moins deux noyaux oxiranne connectés par un groupement hydrocarboné en C₁ à C₁₀₀ qui contient facultativement (a) un ou plusieurs groupes alkyle, groupes amino tertiaires ou halogènes comme substituants sur ce groupement, et/ou (b) un ou plusieurs atomes d'oxygène, atomes de soufre, groupes carboxy, groupes sulfonyle, groupes sulfinyle, groupes cétone, noyaux oxiranne et groupes nitro dans sa chaîne carbonée séparés de l'atome de carbone du noyau oxiranne par au moins un atome de carbone intermédiaire, ledit désémulsionnant contenant au moins 40 % en poids de motifs oxyalkylène dérivés desdits oxydes d'alkylène ayant 3 ou plus de 3 atomes de carbone.
  2. Mélange soluble dans l'huile suivant la revendication 1, dans lequel le bis-époxyde comprend un éther de diglycidyle de bis-phénol A.
  3. Mélange soluble dans l'huile suivant la revendication 1 ou la revendication 2, dans lequel le constituant (i) du type oxyde d'alkylène de l'additif désémulsionnant est l'oxyde de propylène.
  4. Mélange soluble dans l'huile suivant la revendication 3, dans lequel l'additif désémulsionnant comprend des motifs oxyalkylène dérivés de l'oxyde de butylène.
  5. Mélange soluble dans l'huile suivant l'une quelconque des revendications 1 à 4, dans lequel l'alcool polyhydroxylique comprend un polyoxyalkylène-glycol.
  6. Mélange soluble dans l'huile suivant la revendication 5, dans lequel le polyoxyalkylène-glycol possède une moyenne numérique du poids moléculaire de 1000 à 10 000.
  7. Mélange soluble dans l'huile suivant la revendication 6, dans lequel le polyoxyalkylène-glycol comprend le polypropylène-glycol.
  8. Mélange soluble dans l'huile suivant la revendication 7, dans lequel le polypropylène-glycol possède une moyenne numérique du poids moléculaire de 2000 à 8000.
  9. Mélange soluble dans l'huile suivant l'une quelconque des revendications 1 à 8, dans lequel l'additif sans cendre comprend le produit de réaction (a) d'une matière du type acide dicarboxylique mono-insaturé en C₄ à C₁₀ à substituant hydrocarbyle formée par réaction d'un polymère oléfinique d'une mono-oléfine en C₂ à C₁₀ ayant une moyenne numérique du poids moléculaire d'au moins 900 et d'une matière du type acide mono-insaturé en C₄ à C₁₀ ayant une moyenne d'au moins 0,8 groupement producteur d'acide dicarboxylique par molécule dudit polymère oléfinique présente dans le mélange réactionnel utilisé pour former ladite matière acide, et (b) d'un corps réactionnel nucléophile choisi dans le groupe consistant en amines, alcools, amino-alcools et leurs mélanges.
  10. Mélange soluble dans l'huile suivant la revendication 9, dans lequel le corps réactionnel nucléophile comprend une polyalkylènepolyamine dans laquelle les groupes alkylène contiennent 2 à 40 atomes de carbone, ladite polyalkylènepolyamine contenant 2 à environ 9 atomes d'azote par molécule.
  11. Mélange soluble dans l'huile suivant la revendication 10, dans lequel le polymère oléfinique comprend un polyisobutylène ayant une moyenne numérique du poids moléculaire de 1500 à 3000, et dans lequel la matière du type acide mono-insaturé comprend l'anhydride maléique.
  12. Mélange soluble dans l'huile suivant l'une quelconque des revendications 1 à 11, qui contient en outre au moins un additif détergent métallique (D) comprenant au moins un sel de magnésium, de calcium ou de baryum d'une matière choisie dans le groupe consistant en acides sulfoniques, alkylphénols, alkylphénols sulfurés, salicylates et naphténates d'alkyle.
  13. Mélange soluble dans l'huile suivant l'une quelconque des revendications 1 à 12, qui contient en outre 0,1 à 5 parties en poids de l'additif (B) d'au moins un additif de compatibilité (C) comprenant un ester ou dérivé d'hydroxyamide d'un acide mono- ou polycarboxylique ayant un nombre total de 24 à 90 atomes de carbone et au moins environ un groupe acide carboxylique par molécule avec un alcool mono-, di- ou trihydroxylique.
  14. Mélange soluble dans l'huile suivant la revendication 13, dans lequel l'additif de compatibilité comprend un ester de glycol ayant 2 ou 3 groupes acide carboxylique par molécule.
  15. Mélange soluble dans l'huile suivant la revendication 14, dans lequel l'additif de compatibilité comprend au moins un ester ou diester partiel de formule :



            HO-J'-OOC-J-COOH ou




            HO-J'-OOC-J-COOJ''-OH



    dans laquelle J représente le radical hydrocarboné d'un acide polycarboxylique aliphatique saturé ou insaturé ayant un nombre total de 24 à 90 atomes de carbone et 2 ou 3 groupes acide carboxylique par molécule avec au moins 9 atomes de carbone entre les groupes acide carboxylique, J' et J'' sont identiques ou différents et comprennent chacun le radical hydrocarboné d'un alcane-diol ou d'un radical oxyalkylène.
  16. Mélange soluble dans l'huile suivant l'une quelconque des revendications 13 à 15, dans lequel l'additif de compatibilité est utilisé en une quantité de 0,5 à 1,5 partie en poids sur la base du poids total de l'additif désémulsionnant (B) dans le mélange soluble dans l'huile.
  17. Mélange soluble dans l'huile suivant la revendication 13, dans lequel l'additif de compatibilité comprend au moins un ester d'un acide cyclohexènedicarboxylique substitué formé par une condensation thermique de Diels-Alder d'acides gras insaturés en C₁₈ à C₂₂.
  18. Mélange soluble dans l'huile suivant la revendication 17, dans lequel l'acide gras insaturé comprend l'acide oléique, l'acide linoléique ou un de leurs mélanges.
  19. Mélange soluble dans l'huile suivant la revendication 18, dans lequel l'additif de compatibilité comprend un ester de formule :
    Figure imgb0046
     dans laquelle D représente un groupe
    Figure imgb0047
     x' représente un nombre entier de 1 à 100.
  20. Concentré d'additif pour huile lubrifiante, contenant 10 à 80 % en poids d'un mélange soluble dans l'huile suivant l'une quelconque des revendications précédentes, dissous dans une huile hydrocarbonée.
  21. Concentré suivant la revendication 20, comprenant :
    3 à 45 % en poids d'un des dispersants sans cendre (A) (1)
    0,01 à 3 % en poids d'un des additifs désémulsionnants (B)
    0,0005 à 2 % en poids d'un des additifs de compatibilité (C), et
    2 à 45 % en poids d'un des additifs détergents métalliques (D).
  22. Procédé pour former un concentré suivant la revendication 20 ou la revendication 21, dans lequel un des dispersants sans cendre (A) (1) et un des constituants détergents métalliques (D) sont mélangés préalablement à une température de 70 à 130°C, et dans lequel un des additifs désémulsionnants (B) et un des additifs de compatibilité (C) sont mélangés séparément, et les mélanges distincts sont ensuite mélangés l'un à l'autre.
  23. Composition de lubrifiant comprenant un concentré suivant la revendication 20 ou 21 ou pouvant être obtenue par le procédé suivant la revendication 22, diluée avec 3 à 100 parties en poids (par partie en poids de concentré) d'une huile lubrifiante.
EP89301931A 1988-02-26 1989-02-27 Compositions démulsionnées d'huiles lubrifiantes Expired - Lifetime EP0330522B1 (fr)

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DK88089A (da) 1989-08-27
NO890785D0 (no) 1989-02-24
JPH02229892A (ja) 1990-09-12
IL89210A (en) 1992-06-21
ATE112797T1 (de) 1994-10-15
DE68918728T2 (de) 1995-02-16
BR8900859A (pt) 1989-10-17
JP2696380B2 (ja) 1998-01-14
MX172791B (es) 1994-01-13
MX15063A (es) 1993-06-01
CA1331599C (fr) 1994-08-23
EP0330522A3 (en) 1990-02-07
IL89210A0 (en) 1989-09-10
EP0330522A2 (fr) 1989-08-30
AU611264B2 (en) 1991-06-06
AU3071089A (en) 1989-08-31
DK88089D0 (da) 1989-02-24
ES2060752T3 (es) 1994-12-01
NO890785L (no) 1989-08-28
DE68918728D1 (de) 1994-11-17

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