EP0384720B1 - Compositions d'huile lubrifiante pour carter-moteur et des additifs pour utilisation dans celles-ci - Google Patents

Compositions d'huile lubrifiante pour carter-moteur et des additifs pour utilisation dans celles-ci Download PDF

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Publication number
EP0384720B1
EP0384720B1 EP90301833A EP90301833A EP0384720B1 EP 0384720 B1 EP0384720 B1 EP 0384720B1 EP 90301833 A EP90301833 A EP 90301833A EP 90301833 A EP90301833 A EP 90301833A EP 0384720 B1 EP0384720 B1 EP 0384720B1
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Prior art keywords
alkyl
composition
carbon atoms
radical
para
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EP90301833A
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German (de)
English (en)
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EP0384720A1 (fr
Inventor
Terence Colclough
Andrew James Dalziel Ritchie
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ExxonMobil Chemical Patents Inc
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Exxon Chemical Patents Inc
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    • 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
    • C10M167/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound, a non-macromolecular compound and a compound of unknown or incompletely defined constitution, 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
    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
    • C10M129/95—Esters
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • 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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    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/02—Polyethene
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    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
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    • C10M2205/026—Butene
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    • C10M2207/02—Hydroxy compounds
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Definitions

  • This invention relates to crankcase lubricating oil compositions containing anti-oxidants and to additives for use therein.
  • crankcase lubricating oils used in internal combustion engines in automobiles and trucks rapidly become contaminated, in use, with iron compounds which catalyse oxidation of the oil.
  • This oxidation which is also promoted by the elevated temperatures to which the oils are subjected, contributes to the formation of undesirable sludge and also causes the oil to thicken or even solidify.
  • crankcase lubricants an antioxidant to improve the useful life of the oil by reducing sludge formation and thickening.
  • the requirements for antioxidants for use in such oils have become more stringent, more particularly because gasoline and diesel engines are often operated at higher running temperatures than heretofore, and this increases the rate of oxidation of oils used therein.
  • the invention is concerned with the problem of providing an improved antioxidant for use in an environment in which iron-catalysed oxidation reactions can take place. More particularly, the invention is concerned with the problem of providing an improved antioxidant for crankcase lubricating oils while maintaining the balance of other properties of such oils, such as sludge and wear control.
  • British Patent Specification GB-A-760 315 discloses the use of certain substituted aminodiphenylamines to enhance the stability of organic compounds, for example, to stabilize materials such as petrol and aldehydes against oxidation when standing in contact with air.
  • US-A-2 451 652 discloses the use of unsubstituted or alkyl-substituted phenylene diamines to inhibit the oxidation of refined hydrocarbon oils in the presence of metal catalysts.
  • US-A-4 032 462 discloses an antioxidant composition for crankcase lubricating oils, the composition comprising an oil-soluble antimony compound and an antioxidant selected from oil-soluble, sterically hindered phenols or thiophenols or aromatic amines, for example, amino phenols, naphthyl-phenyl amines and phenyl alkyl amines.
  • the present invention provides a crankcase lubricating oil composition which comprises, as antioxidant, a paraphenylene diamine of the formula: in which R 1 represents an aryl-containing radical selected from unsubstituted aryl radicals, aryl radicals substituted by one or more alkyl or alkenyl radicals of up to 20 carbon atoms each, and aryl-alkyl and aryl-alkenyl radicals with up to 20 carbon atoms in the alkyl or alkenyl moiety and optionally substituted on the aryl moiety by one or more alkyl or alkenyl radicals of up to 20 carbon atoms each, and R 2 represents a radical selected from alkyl and alkenyl radicals of up to 20 carbon atoms, and cycloalkyl and cycloalkenyl radicals of 5 to 7 carbon atoms optionally substituted by one or more alkyl or alkenyl radicals of up to 6 carbon atoms each, the said para-phenylene diamine
  • the invention also provides the use of a paraphenylene diamine as defined above to inhibit iron-catalysed oxidation reactions in crankcase lubricating oils.
  • R 1 in the above formula preferably represents an aryl radical, preferably a phenyl radical, which is unsubstituted or is substituted by one or more alkyl or alkenyl radicals having up to 20 carbon atoms each. More preferably, the radical R 1 is phenyl or alkyl-phenyl with 3 to 18, preferably 6 to 12, carbon atoms in the alkyl group, and R 2 is an alkyl group of 3 to 18, preferably 6 to 12, carbon atoms, cyclohexyl, phenyl, or alkyl-phenyl with 3 to 18, preferably 6 to 12, carbon atoms in the alkyl group.
  • para-phenylene diamines which may be used in accordance with the invention are known compounds which are commercially available.
  • One such compound is that sold under the trade mark Santoflex 134 by Monsanto. This is a para-phenylene diamine of the formula given above in which R 1 is phenyl, and R 2 is a mixture of 1,4-dimethylpentyl and 1,3-dimethylbutyl in the approximate ratio of 2:1.
  • the above-defined para-phenylene diamines are effective antioxidants in crankcase lubricating oils.
  • Advantageous concentrations of the para-phenylene diamines are concentrations in the range of 0.1 to 5, preferably 0.1 to 0.5%, by weight based on the total weight of the oil. At such levels, the para-phenylene diamines have been found to be remarkably effective as inhibiting both oxidation and nitration which are thought to be involved not only in oil thickening but also in the formation of sludge when oils are used in an environment in which iron-catalysed reactions can take place.
  • crankcase lubricating oil compositions for use in an iron-catalysed environment can be prepared in accordance with this invention.
  • Universal type crankcase oils those in which the same lubricating oil compositions are used for either gasoline or diesel engines, may also be prepared.
  • These crankcase lubricating oil formulations conventionally contain several different types of additives that will supply the characteristics that are required for t he particular use. Among these types of additives are included viscosity index improvers, corrosion inhibitors, detergents, dispersants, pour point depressants and antiwear additives. Other antioxidants besides the antioxidants of the invention may also be included.
  • lubricating oil formulations In the preparation of lubricating oil formulations, it is common practice to introduce the additives in the form of a concentrate (a so-called “package” or “ad pack") containing 2.5 to 90 weight percent, e.g. 5 to 75 weight percent, active ingredient in a solvent.
  • the solvent may be a hydrocarbon oil, e.g. a mineral lubricating oil, or other suitable material.
  • these concentrates in turn, may be diluted with 3 to 100 parts by weight of lubricating oil, and preferably in the proportions of 5 to 15 parts by weight of the additive package to 95-85 parts by weight of the lubricating oil.
  • Blending of a lubricating oil composition containing several types of additives typically causes no problems if each additive is added separately.
  • Crankcase lubricating oil compositions for use in an environment in which iron-catalysed oxidation reactions can take place contain, in addition to the para-phenylene diamine antioxidant, also one or more of the following:
  • compositions preferably contain at least an ashless dispersant and/or a viscosity index improver dispersant, a detergent, and an antiwear additive in amounts effective to provide their respective functions.
  • the composition comprises 1 to 10 weight percent of ashless dispersant, 0.1 to 5 weight percent of detergent, and 0 to 2 weight percent of antiwear additive.
  • crankcase lubricating oil compositions of the invention may comprise a major amount of a base lubricating oil.
  • the composition may contain from 80 to 99 weight percent of lubricating oil, and preferably from 85 to 95 weight percent of lubricating oil.
  • lubricating oil includes not only hydrocarbon oils derived from petroleum but also synthetic oils such as alkyl esters of dicarboxylic acids, polyglycols and alcohols, polyalphaolefins, alkyl benzenes, organic esters of phosphoric acids, silicone oils, etc.
  • compositions of this invention are provided in the form of concentrates,
  • a minor amount, e.g. up to about 50 percent by weight, of a solvent, mineral or synthetic oil may be included to improve the handling properties of the concentrate.
  • the preferred ashless dispersant in the compositions of this invention is a long chain hydrocarbyl substituted mono- ordi- carboxylic acid material, i.e. acid, anhydride, or ester, and includes a long chain hydrocarbon, generally a polyolefin, substituted with an alpha or beta unsaturated C 4 to C 10 carboxylic acid material, such as itaconic acid, maleic acid, maleic anhydride, chloromaleic acid, dimethyl fumarate, chloromaleic anhydride, acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, etc.
  • a long chain hydrocarbyl substituted mono- ordi- carboxylic acid material i.e. acid, anhydride, or ester
  • a long chain hydrocarbon generally a polyolefin, substituted with an alpha or beta unsaturated C 4 to C 10 carboxylic acid material, such as itaconic acid, maleic acid, maleic anhydride, chloromaleic
  • the dispersant contains at least about 1.05 moles (e.g., 1.05 to 1.2 moles, or higher) of the acid material per mole of polyolefin.
  • the proportion of the dispersant is preferably from 1 to 10 and especially 3 to 7 weight percent of the lubricating oil.
  • Preferred olefin polymers for the reaction with carboxylic acids are polymers derived from a C 2 to C lo , e.g. C 2 to C 5 , monoolefin.
  • Such olefins include ethylene, propylene, butylene, isobutylene, pentene, octene-1, styrene, etc.
  • the polymers may be homopolymers such as polyisobutylene or copolymers of two or more of such olefins. These include copolymers of: ethylene and propylene; butylene and isobutylene; propylene and isobutylene; etc.
  • copolymers include those in which a minor molar amount of the copolymer monomers, e.g. 1 to 10 mole percent, is a C 4 to C18 diolefin, e.g., a copolymer of isobutylene and butadiene; or a copolymer of ethylene, propylene and 1,4-hexadiene; etc.
  • a minor molar amount of the copolymer monomers e.g. 1 to 10 mole percent
  • a C 4 to C18 diolefin e.g., a copolymer of isobutylene and butadiene; or a copolymer of ethylene, propylene and 1,4-hexadiene; etc.
  • the olefin polymer may be completely saturated, for example an ethylene-propylene copolymer made by a Ziegler-Natta synthesis using hydrogen as a moderator to control molecular weight.
  • the olefin polymers usually have number average molecular weights above about 700, including number average molecular weights within the range of from 1,500 to 5,000 with approximately one double bond per polymer chain.
  • An especially suitable starting material for a dispersant additive is polyisobutylene.
  • the number average molecular weight for such polymers can be determined by several known techniques. A convenient method for such determination is by gel permeation chromatography (GPC) which additionally provides mo- lecularweight distribution information, see W.W. Yua, J.J. Kirkland and D.D. Bly, "Modern Size Exclusion Liquid Chromatography,” John Wiley and Sons, New York, 1979.
  • the olefin polymer and the carboxylic acid material may be simply heated together as disclosed in US-A- 3 361 673 and 3 401 118 to cause a thermal "ene" reaction to take place.
  • the olefin polymer can be first halogenated, for example chlorinated or brominated, to about 1 to 8, preferably 3 to 7, weight percent chlorine or bromine, based on the weight of polymer, by passing chlorine or bromine through the polyolefin at a temperature of 100° to 250°C, e.g.
  • halogenated polymer may then be reacted with sufficient unsaturated acid or anhydride at 100° to 250°C, usually 180° to 220°C, for from 0.5 to 10, e.g. 3 to 8, hours. Processes of this general type are taught in US-A- 3 087 436; 3 172 892; 3 272 746 and others.
  • the olefin polymer, and the unsaturated acid or anhydride are mixed and heated while chlorine is added to the hot material.
  • Processes of this type are disclosed in US-A- 3 215 707; 3 231 587; 3 912 764; 4 110 349; 4 234 435; and GB-A- 1 440 219.
  • halogen When a halogen is used, from 65 to 95 weight percent of the polyolefin normally reacts with the carboxylic acid or anhydride. Thermal reactions, carried out without the use of halogen or a catalyst, cause only from 50 to 75 weight percent of the polyisobutylene to react. Chlorination increases reactivity.
  • the carboxylic acid or anhydride can then be further reacted with amines, alcohols, including polyols, amino-alcohols, etc., to form other useful dispersant additives.
  • amines e.g., amines, alcohols, including polyols, amino-alcohols, etc.
  • the acid or anhydride is to be further reacted, e.g., neutralized, then generally a major proportion of at least 50 percent of the acid units up to all the acid units will be reacted.
  • Useful amine compounds for reaction with the hydrocarbyl substituted carboxylic acid or anhydride include mono- and polyamines of from 2 to 60, e.g., 3 to 20, total carbon atoms and from 1 to 12, e.g., 2 to 8, nitrogen atoms in a molecule. These amines may be hydrocarbyl amines or may be hydrocarbyl amines including other groups, e.g., hydroxy groups, alkoxy groups, amide groups, nitriles, imidazoline groups, and the like. Hydroxy amines with 1 to 6 hydroxy groups, preferably 1 to 3 hydroxy groups, are particularly useful.
  • Preferred amines are aliphatic saturated amines, including those of the general formulae: wherein R 3 , R 4 and R 5 are each hydrogen; C 1 to C 25 straight or branched chain alkyl radicals; C 1 to C 12 alkoxy-(C 2 to C 6 alkylene) radicals; C 2 to C 12 alkylamino-(C 2 to C 6 alkylene) radicals; each s can be the same or a different number of from 2 to 6, preferably 2 to 4; and t is a number of from 0 to 10, preferably 2 to 7. At least one of R 3 , R 4 and R 5 must be hydrogen.
  • Suitable amines include: 1,2-diaminoethane; 1,3-diaminopropane: 1,4-diaminobutane; 1,6-diaminohexane; polyethylene amines such as diethylene triamine; triethylene tetramine; tetraethylene pentamine; polypropylene amines such as 1,2-propylene diamine; di-(1,2-propylene)triamine; di(1,3-propylene)-triamine; N,N-dimethyl-1,3-diaminopropane; N,N-di-(2-aminoethyl) ethylene diamine; N,N-di(2-hydroxyethyl)-1,3-propylene diamine; 3-dodecyloxypropylamine; N-dodecyl-1,3-propane diamine; tris hydroxymethylaminomethane (THAM); diisopropanol amine; diethanol amine; triethanol
  • amine compounds include: alicyclic diamines such as 1,4-di-(aminomethyl) cyclohexane, and heterocyclic nitrogen compounds such as imidazolines, and N-aminoalkyl piperazines of the general formula: wherein p 1 and p 2 are the same or different and each is an integer from 1 to 4, and n 1 , n 2 and n 3 are the same or different and each is an integer from 1 to 3. Examples of such amines include 2-pentadecyl imidazoline and N-(2-aminoethyl) piperazine.
  • one process for preparing alkylene amines involves the reaction of an alkylene dihalide (such as ethylene dichloride or propylene dichloride) with ammonia, which results in a complex mixture of alkylene amines wherein pairs of nitrogens are joined by alkylene groups, forming such compounds as diethylene triamine, triethylenetetramine, tetraethylene pentamine and corresponding piperazines.
  • alkylene dihalide such as ethylene dichloride or propylene dichloride
  • ammonia such as ethylene triamine, triethylenetetramine, tetraethylene pentamine and corresponding piperazines.
  • Low cost poly (ethyleneamine) compounds averaging about 5 to 7 nitrogen atoms per molecule are available commercially undertrade names such as "Polyamine H", “Polyamine 400", “Dow Polyamine E-100", etc.
  • Useful amines also include polyoxyalkylene polyamines such as those of the formulae: where m has a value of from 3 to 70, preferably 10 to 35; and where n has a value of about 1 to 40, with the provision that the sum of all the n's is from 3 to 70 and preferably from 6 to 35, and R is a saturated hydrocarbon radical of up to ten carbon atoms, wherein the number of substituents on the Rgroup is from 3 to 6.
  • the alkylene groups in eitherformula (i) or(ii) may be straight or branched chains containing about 2 to 7, and preferably about 2 to 4, carbon atoms.
  • the polyoxyalkylene polyamines above may have average molecular weights ranging from 200 to 4,000 and preferably from 400 to 2,000.
  • the preferred polyoxyalkylene polyamines include the polyoxyethylene and polyoxypropylene diamines and the polyoxypropylene triamines having average molecular weights ranging from 200 to 2,000.
  • the polyoxyalkylene polyamines are commercially available and may be obtained, for example, from the Jefferson Chemical Company, Inc. under the trade name "Jeffamines D-230, D-400, D-1000, D-2000, T-403," etc.
  • the amine is readily reacted with the carboxylic acid material, e.g., alkenyl succinic anhydride, by heating an oil solution containing 5 to 95 weight percent of carboxylic acid material to from 100 to 250°C, preferably 125 to 175°C, generally for 1 to 10, e.g. 2 to 6, hours, until the desired amount of water has been removed.
  • the heating is preferably carried out to favour formation of imides, or mixtures of imides and amides, rather than amides and salts.
  • Reaction ratios can vary considerably, depending upon the reactants, amounts of excess amine, type of bonds formed, etc. Generally from 0.3 to 2, preferably from 0.3 to 1.0, e.g.
  • mole of amine e.g. bis-primary amine
  • mole of the carboxylic acid moiety content e.g. grafted maleic anhydride content.
  • the nitrogen containing dispersant can be further treated by boration as generally taught in US-A-3 087 936 and 3 254 025.
  • Tris (hydroxymethyl) amino methane can be reacted with the aforesaid acid material to form amides, imides or ester type additives as taught by GB-A- 984 409, or to form oxazoline compounds and borated oxazoline compounds as described, for example, in US-A- 4 102 798, 4 116 876 and 4 113 639.
  • the ashless dispersants may also be esters derived from the long chain hydrocarbyl substituted carboxylic acid material and from hydroxy compounds such an monohydric and polyhydric alcohols or aromatic compounds such as phenols and naphthols, etc.
  • the polyhydric alcohols are the most preferred hydroxy compound and preferably contain from 2 to 10 hydroxy radicals, for example, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, and otheralkylene glycols in which the alkylene radical contains from 2 to 8 carbon atoms.
  • polyhydric alcohols include glycerol, mono-oleate of glycerol, monostearate of glycerol, monomethyl ether of glycerol, pentaerythritol, dipentaerythritol, etc.
  • the ester dispersant may also be derived from unsaturated alcohols such as allyl alcohol, cinnamyl alcohol, propargyl alcohol, 1-cyclohexene-3-ol, and oleyl alcohol.
  • unsaturated alcohols such as allyl alcohol, cinnamyl alcohol, propargyl alcohol, 1-cyclohexene-3-ol, and oleyl alcohol.
  • Still other classes of alcohols capable of yielding the esters of this invention comprise the ether-alcohols and amino-alcohols including, for example, the oxy-alkylene, oxy-arylene-, amino-alkylene-, and amino-arylene-substituted alcohols having one or more oxy-alkylene, amino-alkylene or amino-arylene or amino-arylene oxy-arylene radicals.
  • Cellosolve* 1 Cellosolve* 1
  • Carbitol * N,N,N' ,N'-tetrahydroxy-tri-methylene di-amine
  • ether-alcohols having up to about 150 oxy-alkylene radicals in which each alkylene radical contains from 1 to 8 carbon atoms.
  • the ester dispersant may be a di-ester of succinic acid or an acidic ester, i.e. a partially esterified succinic acid; or a partially esterified polyhydric alcohol or phenol, i.e., an ester having free alcoholic or phenolic hydroxyl radicals. Mixtures of the above illustrated esters are likewise contemplated within the scope of this invention.
  • the ester dispersant may be prepared by one of several known methods as illustrated for example in US-A- 3 381 022.
  • Mannich base type dispersants such as those described in US-A- 3 649 229 and 3 798 165 may also be used in these compositions.
  • Such Mannich base dispersants can be formed by reacting a high molecular weight, hydrocarbyl-substituted mono- or polyhydroxy benzene (e.g., having a number average molecular weight of 1,000 or greater) with amines (e.g., polyalkyl polyamines, polyalkenyl polyamines, aromatic amines, carboxylic acid-substituted polyamines and the succinimide formed from any one of these with an olefinic succinic acid or anhydride) and carbonyl compounds (e.g. formaldehyde or para formaldehyde).
  • amines e.g., polyalkyl polyamines, polyalkenyl polyamines, aromatic amines, carboxylic acid-substituted polyamines and the succinimide formed from any one of these with an
  • Avery suitable dispersant is one derived from polyisobutylene substituted with succinic anhydride groups and reacted with polyethylene amines, e.g., tetraethylene pentamine, pentaethylene hexamine, polyoxyethylene and polyoxypropylene amines, e.g., polyoxypropylene diamine, trismethylolaminomethane and pentaerythritol, and combinations thereof.
  • One preferred dispersant combination involves a combination of (A) polyisobutene substituted with succinic anhydride groups and reacted with (B) a hydroxy compound, e.g., pentaer-
  • ythritol (C) a polyoxyalkylene polyamine, e.g., polyoxypropylene diamine, and (D) a polyalkylene polyamine, e.g., polyethylene diamine and tetraethylene pentamine using from 0.3 to 2 moles each of (B) and (D) and from 0.3 to 2 moles of (C) per mole of (A) as described in US-A-3 804 763.
  • a polyoxyalkylene polyamine e.g., polyoxypropylene diamine
  • D a polyalkylene polyamine, e.g., polyethylene diamine and tetraethylene pentamine using from 0.3 to 2 moles each of (B) and (D) and from 0.3 to 2 moles of (C) per mole of (A) as described in US-A-3 804 763.
  • Another preferred dispersant combination involves the combination of (A) polyisobutenyl succinic anhydride with (B) a polyalkylene polyamine, e.g., tetraethylene pentamine, and (C) a polyhydric alcohol or polyhydroxy-substituted aliphatic primary amine, e.g., pentaerythritol or trismethylolaminomethane as described in US-A-3 632 511.
  • Another preferred dispersant is the product of reacting a polybutene with maleic anhydride and reacting the intermediate obtained with a polyalkylene amine containing 2 to 6 carbon atoms per alkylene residue and 2 to 12 nitrogen atoms.
  • Metal-containing rust inhibitors and/or detergents are frequently used with ashless dispersants.
  • Such detergents and rust inhibitors include oil soluble monoand di-carboxylic acids, the metal salts of sulfonic acids, alkyl phenols, sulfurized alkyl phenols, alkyl salicylates and napthenates.
  • these metal-containing rust inhibitors and detergents are used in lubricating oil in amounts of from 0.01 to 10, e.g., 0.1 to 5, weight percent, based on the weight of the total lubricting composition.
  • Highly basic alkali metal and 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 alkali metal or 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 about 3 to more than 30 carbon atoms.
  • haloparaffins for example, haloparaffins, olefins obtained by dehydrogenation of paraffins, polyolefin polymers produced from ethylene, propylene, etc.
  • the alkaryl sulfonates usually contain from 9 to 70 or more carbon atoms, preferably from 16 to 50 carbon atoms per alkyl substituted aromatic moiety.
  • the alkali metal oralkaline earth metal compounds which may be used in neutralizing these alkaryl sulfonic acids to provide the sulfonates include the oxides and hydroxides, alkoxides, carbonates, carboxylates, sulfides, hydrosulfides, nitrates, borates and ethers of sodium, magnesium, calcium, strontium and barium. Examples are calcium oxide, calcium hydroxide, magnesium oxide, 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 100 to 220 percent, although it is preferred to use at least 125 percent of the stoichiometric amount of metal required for complete neutralization.
  • Preferred alkaline earth sulfonate additives are magnesium alkyl aromatic sulfonate having a high total base number as measured by ASTM 02896 ("TBN") ranging from 300 to 400 with the magnesium sulfonate content ranging from 25 to 32 weight percent, based upon the total weight of the additive system dispersed in mineral lubricating oil, and calcium alkyl aromatic sulfonates having a TBN of at least 250, preferably 300-400.
  • 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 napthenates can be realized by utilizing alkaline earth metal, e.g.
  • Such materials include alkaline earth metal, particularly magnesium, calcium, strontium and barium, salts of aromatic acids having the general formula: where Ar is an aryl radical of 1 to 6 rings, R 1 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 (-CH 2 -) 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: with a TBN of 60 to 150 is for example useful in this invention.
  • Another type of basic metal detergent the sulfurized metal phenates
  • the individual R 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 percent by weight, preferably 4 to 12 weight percent 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 neutral or normal sulfurized metal phenates are those in which the ratio of metal to phenol nucleus is about 1:2.
  • the "overbased” or “basic” sulfurized metal phenates are sulfurized metal phenates wherein the ratio of metal to phenol is greater than the stoichiometric ratio, e.g. basic sulfurized metal dodecyl phenate has a metal content up to (or greater) than 100 percent in excess of the metal present in the corresponding normal sulfurized metal phenate. The excess metal is produced in oil-soluble or dispersible form (as by reaction with CO2).
  • Preferred detergents include overbased alkali metal or alkaline earth metal sulfonates and phenates, especially calcium, magnesium or sodium sulphonates and phenates.
  • the detergents which may be included in the compositions of the present invention may optionally be borated in known manner. Such boration provides the detergent with a measure of anti-wear activity.
  • metal-containing detergents comprising calcium and magnesium salts or calcium, magnesium and sodium salts, as described above.
  • anti-wear additives may be included in the compositions of the invention.
  • organic sulphides and polysulphides including especially dialkyl sulphides and polysulphides, e.g., dibutyl polysulphides, and dibenzyl sulphides and polysulphides, which may be substituted, e.g. with halogen, may be incorporated in the compositions.
  • Sulphurized esters e.g. sulphurized methyl or isopropyl oleate and other sulphurized compounds, e.g.
  • sulphurized olefins such as sulphurized diisobutylene, sulphurized tripropylene or sulphurized dipentene may also be added to the compositions.
  • More complex sulphurized compounds such as sulphurized alkyl phenols and sulphurized terpenes and Diels-Alder adducts and sulphurized polymers, e.g. butadiene/butyl acrylate copolymers, may also be used as may sulphurized tall oil fatty acid esters.
  • Esters of beta-thiodipropionic acid e.g. butyl, nonyl, tridecyl or eicosyl esters may also be used.
  • Anti-wear additives in the form of phosphorus esters may also be used.
  • phosphites include dibutyl phosphite, dihexyl phosphite, dicyclohexyl phosphite, alkyl phenyl phosphites, higher alkyl phosphites such as tridecyl phosphite or distearyl phosphite, and mixed phosphites such as dimethylphenyl phosphite and mixed higher alkyl, e.g.
  • oleyl and alkyl phenyl, e.g. 4-pentyl phenyl, phosphite.
  • Phosphites based on polymers such as low molecular weight, polyethylenes and polypropylenes may also be used.
  • Preferred anti-wear additives for addition to the compositions of the present invention are the dihydrocarbyl dithiophosphate metal salts. They also provide some antioxidant activity.
  • the zinc salts are most commonly used in lubricating oils in amounts of 0.1 to 10, preferably 0.2 to 2, weight percent, based upon the total weight of the lubricating oil composition. Salts of other metals, e.g. barium and cadmium, can also be used. They may be prepared in accordance with known techniques by first forming a dithiophosphoric acid, usually be reaction of an alcohol or a phenol with P 2 S 5 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 importing improved antiwear 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 dithiphosphoric acids and may be represented by the following formula: wherein R and R' 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 R and R' 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, s-hexyl, i-hexyl, i-octyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, nonyl-phenyl, dodecyl-cyclohexyl, methylcyclopentyl, propenyl, butenyl, etc.
  • the total number of carbon atoms (i.e., R and R') in the dithiophosphoric acid generally should be about 5 or greater and preferably 8 or greater.
  • Borated derivatives of the aforesaid antiwear agents may also be included in the compositions of the invention.
  • Antioxidants which are especially useful in lubricating oil compositions are based on oil-soluble copper compounds, e.g. in the form of a synthetic or natural carboxylic acid salt.
  • oil-soluble is meant that the compound is oil-soluble or solubilized under normal blending conditions in the oil or additive package.
  • oil-soluble copper compounds include salts of C 10 to C 18 fatty acids such as stearic or palmitic acid; but unsaturated acids (such as oleic acid), branched carboxylic acids (such as naphthenic acids) of molecular weight from 200 to 500, dicarboxylic acids such as polyisobutenyl succinic acids, and synthetic carboxylic acids can all be used because of the acceptable handling and solubility properties of the resulting copper carboxylates.
  • unsaturated acids such as oleic acid
  • branched carboxylic acids such as naphthenic acids
  • dicarboxylic acids such as polyisobutenyl succinic acids
  • synthetic carboxylic acids can all be used because of the acceptable handling and solubility properties of the resulting copper carboxylates.
  • Suitable oil-soluble copper dithiocarbamates have the general formula (RR'N.CS.S) n Cu; where n is 1 or 2 and R and R' may be the same or different hydrocarbyl radicals containing from 1 to 18 carbon atoms each and including radicals such as alkyl, alkenyl, aryl, aralkyl, alkaryl and cycloaliphatic radicals. Particularly preferred as R and R' groups are alkyl groups of 2 to 8 carbon atoms.
  • the radicals may, for example, be ethyl, n-propyl, n-butyl, i-butyl, sec-butyl, amyl, sec-hexyl, i-hexyl, i-octyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, nonyl-phenyl, dodecyl-phenyl, cyclohexyl, methylcyclopentyl, propenyl, butenyl, etc.
  • the total number of carbon atoms i.e., R and R'
  • R and R' generally should be about 5 or greater.
  • Copper salts of dithiophosphonic acids (as described hereinbefore in relation to antiwear additives), copper sulfonates, phenates and acetyl acetonates can also be used.
  • antioxidants can be used in amounts such that, in the final lubricating composition, a copper concentration of from 5 to 500 ppm is present.
  • antioxidants may also be used in the compositions of the invention.
  • antioxidants include hindered phenols, which may contain sulphur, e.g. 4,4'-methylene bis (2,6-di(t-butyl)phenol) and 4,4'-thio bis (2,6-di(t-butyl)phenol); unhindered phenols which again may contain sulphur such as 2,2'-thio bis-(4-nonyl phenol) and 2,2'-methylene bis (4-nonylphenol); diphenylamine derivatives such as 4,4'-dinonyl diphenylamine; phenothiazine derivatives, e.g.
  • alkyl substituents such as dioctyl and dinonyl phenothiazines; substituted beta-naphthylamines such as phenyl beta-naphthylamine and its alkylated derivatives; other amino aryl compounds such as for example 4,4'-bis(secbutylamino) diphenylmethane; dithiocarbonates such as zinc, nickel, copper, or molybdenum dithiocarbamates; and phosphosulphurized olefins, e.g. phosphosulphurized pinene.
  • dioctyl and dinonyl phenothiazines substituted beta-naphthylamines such as phenyl beta-naphthylamine and its alkylated derivatives
  • other amino aryl compounds such as for example 4,4'-bis(secbutylamino) diphenylmethane
  • dithiocarbonates such as zinc, nickel, copper
  • Corrosion inhibitors which act by deactivating metal parts with which they come in contact and/or as sulphur scavengers can also be used in the compositions of the invention.
  • examples of such agents include benzotriazole derivatives; thiadiazole compounds, e.g. 2,5-dimercapto 1,3,4-thiadiazole; mercaptobenzothiazole compounds in the form of amine salts, sulphonamides, thiosulphonamides, and condensates of mercaptobenzothiazole with amines and formaldehyde; salicylaldehyde/diamine condensation products; dialkylphosphites, e.g.
  • dioleyl ordi-2-ethylhexyl phosphite trialkyl and triarylphosphites, e.g. tris-(2-ethylhexyl), triphenyl ortri(4-nonylphenol) phosphites
  • thiophosphonates such as triphenyl or trilauryl thiophosphonate or trilauryl tet- rathiophosphonate.
  • Friction modifiers and fuel economy agents which are compatible with the other ingredients of the new compositions may also be included.
  • examples of such materials are glyceryl monoesters of higher fatty acids, e.g. glyceryl mono-oleate and esters of long-chain polycarboxylic acids with diols, e.g. the butane diol ester of a dimerized unsaturated fatty acid, and oxazoline compounds.
  • Viscosity index improvers are typically polymers of number average molecular weight 10 3 to 10 6- for example ethylene copolymers or polybutenes. Viscosity index improvers may be modified to have dispersant properties and suitable viscosity index improver dispersants for use in compositions of the invention are described in, for example, European Application EP-A-0 024 146, and include
  • Preferred viscosity index improvers with dispersant properties for use in the compositions of the present invention comprise a poly-olefin moiety to which is grafted an unsaturated carboxylic acid moiety, the carboxylic acid groups being reacted with an amine, hydroxyamine or alcohol.
  • the lubricating oil used had the following composition: These agents are all commercially available materials whose exact composition is not significant in the context of the present invention.
  • Ferric acetylacetonate (0.759g) is dissolved in chloroform (100 ml).
  • the lubricating oil 300 g containing a measured amount of the antioxidant under test (or, in the case of the control, no antioxidant) is placed in an oxidation tube (e.g. as required for ASTM D953) and 2.5 ml of the ferric acetylacetonate solution are added (corresponding to 10 ppm of Fe in the oil).
  • An air flow tube is inserted in the oil and air is blown gently through until the ferric acetylacetonate is thoroughly dispersed in the oil.
  • the oxidation tube is then heated to 165°C in a heating block and air is then passed through the heated oil at a rate of 1.7 litres/minute.
  • the viscosity of the oil is measured on a 5 ml sample after 16, 24, 40, 48 and 64 hours using a cone-and- plate (Haake) viscometer (PK 100 and RV 12 with cones PK 5 and PK 1).
  • antioxidants A to H are trade marks.

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Claims (17)

1. Composition d'huile lubrifiante pour carter, qui comprend une huile lubrifiante et, comme anti-oxydant, une paraphénylènediamine de formule :
Figure imgb0015
 dans laquelle R1 représente un radical contenant un groupe aryle choisit entre des radicaux aryle non substitués, des radicaux aryle substitués par un ou plusieurs radicaux alkyle ou alcényle ayant jusqu'à 20 atome de carbone chacun, et des radicaux aryl-alkyle et aryl-alcényle ayant jusqu'à 20 atomes de carbone dans la portion alkyle ou alcényle et facultativement substitués sur la portion aryle par un ou plusieurs radicaux alkyle ou alcényle ayant jusqu'à 20 atomes de carbone chacun, et R2 représente un radical choisi entre des radicaux alkyle et alcényle ayant jusqu'à 20 atomes de carbone, et des radicaux cycloalky- le et cycloalcényle ayant 5 à 7 atomes de carbone, facultativement substitués par un ou plusieurs radicaux alkyle ou alcényle ayant jusqu'à 6 atomes de carbone chacun, ladite paraphénylènediamine étant présente sous forme de la base libre ou d'un sel soluble dans l'huile.
2. Composition suivant la revendication 1, dans laquelle le radical R2 dans la paraphénylènediamine représente un radical cycloaliphatique tel que spécifié dans la revendication 1.
3. Composition suivant la revendication 1 ou la revendication 2, dans laquelle le radical R1 dans la paraphénylènediamine représente un radical aryle, de préférence un radical phényle, qui n'est pas substitué ou qui porte comme substituants un ou plusieurs radicaux alkyle ou alcényle ayant jusqu'à 20 atomes de carbone chacun.
4. Composition suivant l'une quelconque des revendications 1 à 3, dans laquelle, dans la paraphénylènediamine, R1 représente un radical phényle ou alkylphényle ayant 6 à 12 atomes de carbone dans le groupe alkyle, et R2 représente un radical alkyle ayant 6 à 12 atomes de carbone ou un radical cyclohexyle.
5. Composition suivant la revendication 1, dans laquelle, dans la paraphénylènediamine, R1 représente un radical phényle et R2 représente un radical cyclohexyle.
6. Composition suivant la revendication 1, dans laquelle, dans la paraphénylènediamine, R1 représente un radical phényle et R2 représente un radical alkyle à chaîne ramifiée ayant 6 ou 7 atomes de carbone.
7. Composition suivant l'une quelconque des revendications précédentes, qui contient aussi un autre anti-oxydant.
8. Composition suivant l'une quelconque des revendications précédentes, qui contient (a) un dispersant sans cendre et/ou un dispersant améliorant l'indice de viscosité, (b) un agent anti-usure et (c) un détergent.
9. Composition suivant la revendication 8, dans laquelle le dispersant sans cendre est le produit de réaction d'un polymère d'une monooléfine en C2 à C10 ayant une moyenne numérique du poids moléculaire supérieure à environ 700, avec un acide ou anhydride d'acide dicarboxylique mono-insaturé en C4 à C10 et réaction du produit intermédiaire obtenu avec une amine, un alcool, un amino-alcool, ou un mélange de ces corps réactionnels ou une base de Mannich de haut poids moléculaire dérivée d'un monohydroxy- benzène ou d'un polyhydroxybenzène à substituant hydrocarbyle ayant un poids moléculaire supérieur à 1000.
10. Composition suivant la revendication 9, dans laquelle le dispersant sans cendre est le produit de réaction d'un polybutène avec l'anhydride maléique et de réaction du produit intermédiaire obtenu avec une po- lyalkylènamine contenant 2 à 6 atomes de carbone par résidu alkylène et 2 à 12 atomes d'azote.
11. Composition suivant l'une quelconque des revendications 8 à 10, dans laquelle le dispersant améliorant l'indice de viscosité est un groupement polyoléfinique auquel est greffé un groupement acide carboxylique non saturé, les groupes acide carboxylique étant combinés avec une amine, une hydroxyamine ou un alcool.
12. Composition suivant l'une quelconque des revendications 8 à 11, dans laquelle le détergent est un sulfonate ou phénate de métal alcalin ou alcalino-terreux rendu surbasique, de préférence un sulfonate ou phénate de calcium, magnésium, ou sodium.
13. Composition suivant l'une quelconque des revendications 8 à 12, qui comprend une association de détergents comprenant des sels de calcium, magnésium et sodium.
14. Composition suivant l'une quelconque des revendications 8 à 13, dans laquelle l'agent anti-usure comprend un dihydrocarbyldithiophosphate de zinc.
15. Composition suivant l'une quelconque des revendications précédentes, contenant 0,1 à 5 pour cent en poids, par exemple 0,1 à 0,5 pour cent en poids dudit anti-oxydant formé d'une paraphénylènediamine.
16. Composition suivant l'une quelconque des revendications 8 à 15, qui contient 1 à 10 pour cent en poids de dispersant sans cendre, 0,1 à 5 pour cent en poids de détergent et 0 à 2 pour cent en poids d'additif anti-usure.
17. Utilisation d'une paraphénylènediamine telle que définie dans la revendication 1 pour inhiber des réactions d'oxydation, catalysées par le fer, dans des huiles lubrifiantes pour carter.
EP90301833A 1989-02-23 1990-02-21 Compositions d'huile lubrifiante pour carter-moteur et des additifs pour utilisation dans celles-ci Expired - Lifetime EP0384720B1 (fr)

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DE69004828T2 (de) 1994-04-07
JPH02276895A (ja) 1990-11-13
CA2010606A1 (fr) 1990-08-23
EP0384720A1 (fr) 1990-08-29
GB8904203D0 (en) 1989-04-05
CA2010606C (fr) 2000-12-19
DE69004828D1 (de) 1994-01-13
JP2813404B2 (ja) 1998-10-22

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