EP0578495B1 - Lubrifiant pour cycle deux-temps composé d'une huile végétale et d'un conditionnement d'additifs - Google Patents

Lubrifiant pour cycle deux-temps composé d'une huile végétale et d'un conditionnement d'additifs Download PDF

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Publication number
EP0578495B1
EP0578495B1 EP93305348A EP93305348A EP0578495B1 EP 0578495 B1 EP0578495 B1 EP 0578495B1 EP 93305348 A EP93305348 A EP 93305348A EP 93305348 A EP93305348 A EP 93305348A EP 0578495 B1 EP0578495 B1 EP 0578495B1
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Prior art keywords
carbon atoms
group
phenol
composition
aliphatic
Prior art date
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Expired - Lifetime
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EP93305348A
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German (de)
English (en)
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EP0578495A1 (fr
Inventor
William Bricker Chamberlin Iii
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Lubrizol Corp
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Lubrizol Corp
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/045—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution and non-macromolecular compounds
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    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/04—Fatty oil fractions
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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
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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
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Definitions

  • the present invention relates to an additive package dissolved in a naturally occurring triglyceride such that a nitrogen-containing soluble organic composition is obtained.
  • the composition thus obtained has utility in two-stroke cycle, spark-ignited internal combustion engines when combined with fuels before or during use.
  • spark-ignited two-stroke cycle internal combustion engines including rotary engines such as those of the Wankel type has steadily increased. They are presently found in power lawn mowers and other power-operated garden equipment, power chain saws, pumps, electrical generators, marine outboard engines, snow mobiles, motorcycles and the like.
  • US Patent 4,100,082 (Clason et al, July 11, 1978) relates to additive combinations useful in oils of lubricating viscosity and normally liquid fuels. More particularly, this reference relates to additive combinations of amino phenols with certain detergent/dispersants and to oils and fuels containing same which are especially useful in two-stroke cycle engines.
  • US Patent 4,663,063 (Davis, May 5, 1987) relates to additive combinations useful in lubricating compositions containing a major amount of an oil of lubricating viscosity and a minor amount of the additive combination.
  • the lubricants are useful in two-stroke cycle internal combustion engines. More particularly, the reference relates to additive compositions comprising a mixture of at least one alkyl phenol having at least one hydrocarbon-based group of at least about 10 aliphatic carbon atoms and at least one amino compound which is not an aminophenol. Since two-stroke cycle engine oils are often combined with fuels before or during use, this reference also relates to two-stroke cycle fuel-lubricant mixtures.
  • US Patent 4,708,809 (Davis, November 24, 1987) relates to lubricant compositions containing a major amount of an oil of lubricating viscosity and a minor amount of at least one alkyl phenol.
  • the lubricants are useful in two-stroke cycle internal combustion engines. More particularly, the references relates to such oils containing alkyl phenols having at least one hydrocarbon-based group of at least 10 aliphatic carbon atoms. Since two-stroke cycle engine oils are often combined with fuels before or during use, this reference also relates to two-stroke cycle fuel-lubricant mixtures.
  • This invention comprises a nitrogen-containing soluble organic composition comprising a combination of:
  • the invention comprises a nitrogen-containing soluble organic composition comprising a combination of:
  • a natural oil which is vegetable oil of a triglyceride of the formula
  • R 1 , R 2 and R 3 are hydrocarbyl groups independently containing from 8 to 24 carbon atoms.
  • hydrocarbyl group as used herein denotes a radical having a carbon atom directly attached to the remainder of the molecule.
  • the hydrocarbyl group is of predominately aliphatic hydrocarbon character.
  • Such aliphatic hydrocarbon groups include the following:
  • the hydrocarbyl groups may be saturated or unsaturated or a mixture of both.
  • Triglycerides employed within the instant invention include high oleic safflower oil, high oleic rapeseed oil, high oleic sunflower oil, and high- oleic corn oil.
  • Some of the preferred vegetable oils of this invention are high oleic sunflower oil, high oleic rapeseed oil.
  • high oleic being defined as containing at least 70 % oleic content and preferably at least 80 % oleic content.
  • These preferred oils may be obtained from sunflower (Helianthus sp.) available from SVO Enterprises, Eastlake, Ohio as Sunyl R 70 or Sunyl R 80 high oleic sunflower oil, and high oleic corn oil.
  • any naturally occurring oil that is not naturally epoxidized. That is, a natural oil may be reacted with aqueous peracetic acid solution, or with hydrogen peroxide and acetic acid in a manner well known by those skilled in the art.
  • the epoxide content of the synthetically epoxidized natural oils will vary with the degree of completion of the epoxidation reaction and also with the amount of unsaturation present in the triglyceride of the natural oil. Characteristically, such epoxidized oils have an oxirane oxygen content of at least 3%, preferably 5 to 15%.
  • the detergent/dispersant (B) (I) is combined with (A) .
  • a detergent/dispersant is selected from B (II) through (B) (IV) and is combined with A, (B) (I) and (C).
  • detergent/dispersants (B) used in this invention are materials known to those skilled in the art and they have been described in numerous books, articles and patents. A number of these are noted hereinbelow in relation to specific types of detergent/dispersants.
  • a number of acylated, nitrogen-containing compounds having a substituent of at least 10 aliphatic carbon atoms and made by reacting a carboxylic acid acylating agent with an amino compound are known to those skilled in the art.
  • the acylating agent is linked to the amino compound through an imidazoline imido, amido, amidine or acyloxy ammonium linkage.
  • the substituent of 10 aliphatic carbon atoms preferably 30 aliphatic carbon atoms, may be in either the carboxylic acid acylating agent derived portion of the molecule or in the amino compound derived portion of the molecule. Preferably, however, it is in the acylating agent portion.
  • the acylating agent can vary from formic acid and its acylating derivatives to acylating agents having high molecular weight aliphatic substituents of up to 5,000, 10,000 or 20,000 carbon atoms.
  • the amino compounds can vary from ammonia itself to amines having aliphatic substituents of up to 30 carbon atoms.
  • a typical class of acylated amino compounds useful in making the compositions of this invention are those made by reacting an acylating agent having an aliphatic substituent of at least 10 carbon atoms and a nitrogen compound characterized by the presence of at least one -NH group.
  • the acylating agent will be a mono- or polycarboxylic acid (or reactive equivalent thereof) such as a substituted succinic or propionic acid and the amino compound will be a polyamine or mixture of polyamines, most typically, a mixture of ethylene polyamines.
  • the aliphatic substituent in such acylating agents is often of at least 50 and up to 400 carbon atoms.
  • the aliphatic substituted is derived from homopolymerized or interpolymerized C 2-10 1-olefins or mixtures of both. Usually it is derived from ethylene, propylene, butylene and mixtures thereof. Typically, it is derived from polymerized isobutene.
  • the amino compounds useful in making these acylated compounds are the following: polyalkylene polyamines of the general formula wherein R 8 is a hydrogen atom, n is a whole number of 1 to 10 and U is a C 2-10 alkylene group.
  • Specific examples of the polyalkylene polyamines (1) are ethylene diamine, tetra(ethylene)pentamine, tri-(trimethylene)tetramine, 1,2-propylene diamine, etc.
  • a typical acylated nitrogen-containing compound of this class is that made by reacting a poly(isobutene)-substituted succinic anhydride acylating agent (e.g., anhydride, acid, ester, etc.) wherein the poly(isobutene) substituent has between 50 to 400 carbon atoms with a mixture of ethylene polyamines having 3 to 7 amino nitrogen atoms per ethylene polyamine and 1 to 6 ethylene units made from condensation of ammonia with ethylene chloride.
  • a poly(isobutene)-substituted succinic anhydride acylating agent e.g., anhydride, acid, ester, etc.
  • acylated nitrogen compound belonging to this class is that made by reacting the afore-described alkylene amines with the afore-described substituted succinic acids or anhydrides and aliphatic mono-carboxylic acids having from 2 to 22 carbon atoms.
  • the mole ratio of succinic acid to mono-carboxylic acid ranges from about 1:0.1 to about 1:1.
  • Typical of the mono-carboxylic acid are formic acid, acetic acid, dodecanoic acid, butanoic acid, oleic acid, stearic acid, the commercial mixture of stearic acid isomers known as isostearic acid, tolyl acid, etc.
  • Such materials are more fully described in U.S. Patents 3,216,936 and 3,250,715.
  • Still another type of acylated nitrogen compound useful in making the compositions of this invention is the product of the reaction of a fatty monocarboxylic acid of 12-30 carbon atoms and the afore-described alkylene amines, typically, ethylene, propylene or trimethylene polyamines containing 2 to 8 amino groups and mixtures thereof.
  • the fatty monocarboxylic acids are generally mixtures of straight and branched chain fatty carboxylic acids containing 12-30 carbon atoms.
  • a widely used type of acylated nitrogen compound is made by reacting the afore-described alkylene polyamines with a mixture of fatty acids having from 5 to 30 mole percent straight chain acid and 70 to 95 percent mole branched chain fatty acids.
  • the branched chain fatty acids can also include those in which the branch is not alkyl in nature, such as found in phenyl and cyclohexyl stearic acid and the chloro-stearic acids.
  • Branched chain fatty carboxylic acid/alkylene polyamine products have been described extensively in the art. See for example, U.S. Patents 3,110,673; 3,251,853; 3,326,801; 3,337,459; 3,405,064; 3,429,674; 3,468,639; 3,857,791.
  • metal used to make these salts is usually not critical and therefore virtually any metal can be used. For reasons of availability, cost and maximum effectiveness, certain metals are more commonly used. These include the alkali and alkaline earth metals (i.e., the Group IA and IIA metals excluding francium and radium). Group IIB metals as well as polyvalent metals such as aluminum, chromium, molybdenum, tungsten, manganese, iron, cobalt, nickel, and copper can also be used. Salts containing a mixture of ions of two or more of these metals are often used.
  • salts can be neutral or basic.
  • the former contain an amount of metal cation just sufficient to neutralize the acidic groups present in the salt anion; the former contain an excess of metal cation and are often termed overbased, hyperbased or superbased salts.
  • These basic and neutral salts can be of oil-soluble organic sulfur acids such as sulfonic, sulfamic, thiosulfonic, sulfinic, sulfenic, partial ester sulfuric, sulfurous and thiosulfuric acid. Generally they are salts of carbocyclic or aliphatic sulfonic acids.
  • the carbocyclic sulfonic acids include the mono- or poly-nuclear aromatic or cycloaliphatic compounds.
  • the oil soluble sulfonates can be represented for the most part by the following formulae: [R x T-(S0 3 ) y ] z M b [R 10 ⁇ (SO 3 ) a ] d M b
  • M is either a metal cation as described hereinabove or hydrogen
  • T is a cyclic nucleus such as, for example, benzene, naphthalene, anthracene, phenanthrene, diphenylene oxide, thianthrene, phenothioxine, diphenylene sulfide, phenothiazine, diphenyl oxide, diphenyl sulfide, diphenylamine, cyclohexane, petroleum naphthenes, decahydro-naphthalene, cyclopentane, etc.;
  • R 10 in Formula VII is an aliphatic radical containing at least 15 carbon atoms and M is either a metal cation or hydrogen.
  • types of the R 10 radical are alkyl, alkenyl, alkoxyalkyl, carboalkoxyalkyl, etc.
  • Specific examples of R 10 are groups derived from petrolatum, saturated and unsaturated paraffin wax, and polyolefins, including polymerized C2, C3, C4, C5, C6, etc., olefins containing from 15 to 7000 or more carbon atoms.
  • the groups T, R, and R 10 in the above formulae can also contain other inorganic or organic substituents in addition to those enumerated above such as, for example, hydroxy, mercapto, halogen, nitro, amino, nitroso, sulfide, disulfide, etc.
  • substituents for example, hydroxy, mercapto, halogen, nitro, amino, nitroso, sulfide, disulfide, etc.
  • x, y, z and b are at least 1
  • Formula VII a, b and d are at least 1.
  • oil-soluble sulfonic acids coming within the scope of Formulae VI and VII above, and it is to be understood that such examples serve also to illustrate the salts of such sulfonic acids useful in this invention.
  • sulfonic acids are mahogany sulfonic acids; bright stock sulfonic acids; sulfonic acids derived from lubricating oil fractions having a Saybolt viscosity from 100 seconds at 100°F.
  • the latter are acids derived from benzene which has been alkylated with propylene tetramers or isobutene trimers to introduce 1, 2, 3, or more branched-chain Cl2 substituents on the benzene ring.
  • Dodecyl benzene bottoms principally mixtures of mono- and di-dodecyl benzenes, are available as by-products from the manufacture of household detergents. Similar products obtained from alkylation bottoms formed during manufacture of linear alkyl sulfonates (LAS) are also useful in making the sulfonates used in this invention.
  • aliphatic sulfonic acids such as paraffin wax sulfonic acids, unsaturated paraffin wax sulfonic acids, hydroxy-substituted paraffin wax sulfonic acids, hexapropylene sulfonic acids, tetra-amylene sulfonic acids, polyisobutene sulfonic acids wherein the polyisobutene contains from 20 to 7000 or more carbon atoms, chloro-substituted paraffin wax sulfonic acids, nitro-paraffin wax sulfonic acids, etc.; cycloaliphatic sulfonic acids such as petroleum naphthene sulfonic acids, cetyl cyclopentyl sulfonic acids, lauryl cyclohexyl sulfonic acids, bis-(di-isobutyl) cyclohexyl sulfonic acids, mono- or poly-wax substituted cyclohexy
  • the carboxylic acids from which suitable neutral and basic salts for use in this invention can be made include aliphatic, cycloaliphatic, and aromatic mono- and polybasic carboxylic acids such as the naphthenic acids, alkyl- or alkenyl-substituted cyclopentanoic acids, alkyl- or alkenyl substituted cyclohexanoic acids, alkyl- or alkenyl-substituted aromatic carboxylic acids.
  • the aliphatic acids generally contain at least eight carbon atoms and preferably at least twelve carbon atoms. Usually they have no more than 400 carbon atoms. Generally, if the aliphatic carbon chain is branched, the acids are more oil-soluble for any given carbon atom content.
  • the cycloaliphatic and aliphatic carboxylic acids can be saturated or unsaturated. Specific examples include 2-ethylhexanoic acid, ⁇ -linolenic acid, propylene-tetramer-substituted maleic acid, behenic acid, isostearic acid, pelargonic acid, capric acid, palmitoleic acid, linoleic acid, lauric acid, oleic acid, ricinlic acid, undecylic acid, dioctylcyclopentane carboxylic acid, myristic acid, dilauryldecahydronaphthalene carboxylic acid, stearyloctahydroindene carboxylic acid, palmitic acid, commercially available mixtures of two or more carboxylic acids such as tall oil acids, rosein acids, and the like.
  • a preferred group of oil-soluble carboxylic acids useful in preparing the salts used in the present invention are the oil-soluble aromatic carboxylic acids. These acids are represented by the general formula: where R 11 is an aliphatic hydrocarbon-based group of at least four carbon atoms, and no more than 400 aliphatic carbon atoms, a is an integer of from one to four, Ar* is a polyvalent aromatic hydrocarbon nucleus of up to 14 carbon atoms each, X is independently a sulfur or oxygen atom, and m is an integer of from one to four with the proviso that R 11 and a are such that there is an average of at least 8 aliphatic carbon atoms provided by the R 11 groups for each acid molecule represented by Formula VIII.
  • aromatic nuclei represented by the variable Ar* are the polyvalent aromatic radicals derived from benzene, naphthalene, anthracene, phenanthrene, indene, fluorene, biphenyl, and the like.
  • the radical represented by Ar* will be a polyvalent nucleus derived from benzene or naphthalene such as phenylenes and naphthylene, e.g., methylphenylenes, ethoxyphenylenes, nitrophenylenes, isopropylphenylenes, hydroxyphenylenes, mercaptophenylenes, N,N-diethylaminophenylenes, chlorophenylenes, dipropoxynaphthylenes, tri-ethylnaphthylenes, and similar tri-, tetra-, pentavalent nuclei thereof, etc.
  • phenylenes and naphthylene e.g., methylphenylenes, ethoxyphenylenes, nitrophenylenes, isopropylphenylenes, hydroxyphenylenes, mercaptophenylenes, N,N-diethylaminophenylenes, chloroph
  • the R 11 groups are usually purely hydrocarbyl groups, preferably groups such as alkyl or alkenyl radicals.
  • R 11 groups include butyl, isobutyl, pentyl, octyl, nonyl, dodecyl, docosyl, tetracontyl, 5-chlorohexyl, 4-ethoxypentyl, 4-hexenyl, 3-cyclohexyloctyl, 4-(p-chlorophenyl)-octyl, 2,3,5-trimethylheptyl, 4-ethyl-5-methyloctyl, and substituents derived from polymerized olefins such as polychloroprenes, polyethylenes, polypropylenes, polyisobutylenes, ethylene-propylene copolymers, chlorinated olefin polymers, oxidized ethylene-propylene copolymers, and the like
  • the group Ar* may contain non-hydrocarbon substituents, for example, such diverse substituents as lower alkoxy, lower alkyl mercapto, nitro, halo, alkyl or alkenyl groups of less than four carbon atoms, hydroxy, mercapto, and the like.
  • a group of particularly useful carboxylic acids are those of the formula: where R 11 , X, AR*, m and a are as defined in Formula VIII and p is an integer of 1 to 4, usually 1 or 2.
  • an especially preferred class of oil-soluble carboxylic acids are those of the formula: where R 12 in Formula X is an aliphatic hydrocarbon group containing at least 4 to 400 carbon atoms, a is an integer of from 1 to 3, b is 1 or 2, c is zero, 1, or 2 and preferably 1 with the proviso that R 12 and a are such that the acid molecules contain at least an average of about twelve aliphatic carbon atoms in the aliphatic hydrocarbon substituents per acid molecule.
  • each aliphatic hydrocarbon substituent contains an average of at least about sixteen carbon atoms per substituent and one to three substituents per molecule are particularly useful.
  • Salts prepared from such salicylic acids wherein the aliphatic hydrocarbon substituents are derived from polymerized olefins, particularly polymerized lower l-mono-olefins such as polyethylene, polypropylene, polisobutylene, ethylene/propylene copolymers and the like and having average carbon contents of 30 to 400 carbon atoms.
  • carboxylic acids corresponding to Formulae VIII-IX above are well known or can be prepared according to procedures known in the art.
  • Carboxylic acids of the type illustrated by the above formulae and processes for preparing their neutral and basic metal salts are well known and disclosed, for example, in such U.S. Patents as 2,197,832; 2,197,835; 2,252,662; 2,252,664; 2,714,092, 3,410,798 and 3,595,791.
  • a commonly available class of phenates are those made from phenols of the general formula wherein a is an integer of 1-3, b is of 1 or 2, z is 0 or 1, R 13 in Formula XIII is a substantially saturated hydrocarbon based substituent having an average of from 30 to 400 aliphatic carbon atoms and R 14 is selected from lower alkyl, lower alkoxyl, nitro, and halo groups.
  • One particular class of phenates for use in this invention are the basic (i.e., overbased, etc.) Group IIA metal sulfurized phenates made by sulfurizing a phenol as described hereinabove with a sulfurizing agent such as sulfur, a sulfur halide, or sulfide or hydrosulfide salt. Techniques for making these sulfurized phenates are described in U.S Patents 2,680,096; 3,036,971 and 3,775,321.
  • phenates that are useful are those that are made from phenols that have been linked through alkylene (e.g., methylene) bridges. These are made by reacting single or multi-ring phenols with aldehydes or ketones, typically, in the presence of an acid or basic catalyst.
  • alkylene e.g., methylene
  • Such linked phenates as well as sulfurized phenates are described in detail in U.S. Patent 3,350,038; particularly columns 6-8 thereof.
  • neutral and basic salts of the hereinabove described organic sulfur acid, carboxylic acids and phenols
  • the neutral and basic salts will be sodium, lithium, magnesium, calcium, or barium salts including mixtures of two or more of any of these.
  • hydrocarbyl-substituted amines used in making the compositions of this invention are well known to those of skill in the art and they are described in a number of patents. Among these are U.S. Patents 3,275,554; 3,438,757; 3,454,555; 3,565,804; 3,755,433; and 3,822,209.
  • hydrocarbyl amines useful in this invention include monoamines of the general formula AXNR 7 .
  • Illustrative of such monoamines are the following:
  • hydrocarbyl substituted amines useful in forming the compositions in this invention include certain N-amino-hydrocarbyl morpholines which are not embraced in the general Formula XIV above.
  • These hydrocarbyl-substituted aminohydrocarbyl morpholines have the general formula: wherein R 7 is an aliphatic hydrocarbon group of from 30 to 400 carbons, A is hydrogen, hydrocarbyl of from 1 to 10 carbon atoms or hydroxy hydrocarbyl group of from 1 to 10 carbon atoms and U is an alkylene group of from 2 to 10 carbon atoms.
  • R 7 is an aliphatic hydrocarbon group of from 30 to 400 carbons
  • A is hydrogen, hydrocarbyl of from 1 to 10 carbon atoms or hydroxy hydrocarbyl group of from 1 to 10 carbon atoms
  • U is an alkylene group of from 2 to 10 carbon atoms.
  • the phenol/aldehyde/amino compound condensates useful in making the compositions of this invention include those generically referred to as Mannich condensates. Generally they are made by reacting simultaneously or sequentially at least one active hydrogen compound such as a hydrocarbon - substituted phenol (e.g., an alkyl phenol wherein the alkyl group has at least 30 up to 400 carbon atoms), having at least one hydrogen atom bonded to an aromatic carbon, with at least one aldehyde or aldehyde-producing material (typically formaldehyde or formaldehyde precursor) and at least one amino or polyamino compound having at least one NH group.
  • a hydrocarbon - substituted phenol e.g., an alkyl phenol wherein the alkyl group has at least 30 up to 400 carbon atoms
  • aldehyde or aldehyde-producing material typically formaldehyde or formaldehyde precursor
  • the amino compounds include primary or secondary mono-amines having hydrocarbon substituents of 1 to 30 carbon atoms or hydroxyl-substituted hydrocarbon substituents of 1 to 30 carbon atoms.
  • Another type of typical amino compound are the polyamines described during the discussion of the acylated nitrogen-containing compounds.
  • Exemplary mono-amines include methyl ethyl amine, methyl octadecyl amine, aniline, diethyl amine, diethanol amine, dipropyl amine and so forth.
  • U.S. Patents contain extensive descriptions of Mannich condensates which can be used in making the compositions of this invention: U.S.
  • Condensates made from sulfur-containing reactants can also be used in the compositions of the present invention. Such sulfur-containing condensates are described in U.S. Patent 3,368,972; 3,649,229; 3,600,372; 3,649,659; and 3,741,896.
  • the condensates used in making the compositions of this invention are made from a phenol bearing an alkyl substituent of 6 to 400 carbon atoms,more typically, 30 to 250 carbon atoms.
  • These typical condensates are made from formaldehyde or C 2-7 aliphatic aldehyde and an amino compound such as those used in making the acylated nitrogen-containing compounds described under (B) (I).
  • the amino compound may also include (2) heterocyclic-substituted polyamines of the formula wherein R 8 and U are as defined hereinabove, m is 0 or a whole number of 1 to 10, m' is a whole number of 1 to 10 and Y is an oxygen or divalent sulfur atom or a N-R 8 group and (3) aromatic polyamines of the general formula Ar(NR 8 2 ) y wherein Ar is an aromatic nucleus of 6 to 20 carbon atoms, each R 8 is as defined hereinabove and y is 2 to 8.
  • heterocyclic-substituted polyamines (2) are N-2-aminoethyl piperazine, N-2 and N-3 amino propyl morpholine, N-3-(dimethyl amino) propyl piperazine, etc.
  • aromatic polyamines (3) are the various isomeric phenylene diamines, the various isomeric naphthylene diamines, etc.
  • a particularly preferred class of condensation products for use in the present invention are those made by a "2-step process" as disclosed in commonly assigned U.S. Serial No. 451,644, filed March 15, 1974 and published as U.S. patent 4,454,059.
  • these nitrogen containing condensates are made by (1) reacting at least one hydroxy aromatic compound containing an aliphatic-based or cycloaliphatic-based substituent which has at least 30 carbon atoms and up to 400 carbon atoms with a lower aliphatic C 1-7 aldehyde or reversible polymer thereof in the presence of an alkaline reagent, such as an alkali metal hydroxide, at a temperature up to 150°C.; (2) substantially neutralizing the intermediate reaction mixture thus formed; and (3) reacting the neutralized intermediate with at least one compound which contains an amino group having at least one -NH group.
  • an alkaline reagent such as an alkali metal hydroxide
  • these 2-step condensates are made from (a) phenols bearing a hydrocarbon-based substituent having 30 to 250 carbon atoms, said substituent being derived from a polymer of propylene, l-butene, 2-butene, or isobutene and (b) formaldehyde, or reversible polymer thereof, (e.g., trioxane, paraformaldehyde) or functional equivalent thereof, (e.g., methylal) and (c) an alkylene polyamine such as ethylene polyamines having between 2 and 10 nitrogen atoms.
  • formaldehyde, or reversible polymer thereof e.g., trioxane, paraformaldehyde
  • functional equivalent thereof e.g., methylal
  • an alkylene polyamine such as ethylene polyamines having between 2 and 10 nitrogen atoms.
  • the aromatic moiety, Ar, of Formula II can be a single aromatic nucleus such as a benzene nucleus, a pyridine nucleus, a thiophene nucleus, a 1,2,3,4-tetrahydronaphthalene nucleus, etc., or a polynuclear 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, etc.
  • such 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.
  • bridging linkages can be chosen from carbon-to-carbon single bonds, ether linkages, keto linkages, sulfide linkages, polysulfide linkages of 2 to 6 sulfur atoms, sulfonyl 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.
  • more than one bridging linkage can be present in Ar between aromatic nuclei.
  • a fluorene nucleus has two benzene nuclei linked by both a methylene linkage and a covalent bond.
  • Such a nucleus may be considered to have 3 nuclei but only two of them are aromatic.
  • Ar will contain only carbon atoms in the aromatic nuclei per se (plus any lower alkyl or alkoxy substituent present).
  • the number of aromatic nuclei, fused, linked or both, in Ar can play a role in determining the integer values of a, b and c in Formula II.
  • a, b and c are each independently 1 to 4.
  • a, b and c can each be an integer of 1 to 8, that is, up to three times the number of aromatic nuclei present (in naphthalene, 2).
  • a, b and c can each be an integer of 1 to 12.
  • Ar is a biphenyl or a naphthyl moiety
  • a, b and c can each independently be an integer of 1 to 8.
  • the values of a, b and c are obviously limited by the fact that their sum cannot exceed the total unsatisfied valences of Ar.
  • the single ring aromatic nucleus which can be the Ar moiety can be represented by the general formula ar(Q) m wherein ar represents a single ring aromatic nucleus (e.g., benzene) of 4 to 10 carbons, each Q independently represents a lower alkyl group, lower alkoxy group, nitro group, or halogen atom, and m is 0 to 3.
  • ar represents a single ring aromatic nucleus (e.g., benzene) of 4 to 10 carbons
  • each Q independently represents a lower alkyl group, lower alkoxy group, nitro group, or halogen atom
  • m is 0 to 3.
  • "lower” refers to groups having 7 or less carbon atoms such as lower alkyl and lower alkoxyl groups.
  • Halogen atoms include fluorine, chlorine, bromine and iodine atoms; usually, the halogen atoms are fluorine and chlorine atoms.
  • single ring Ar moieties are the following: etc. wherein Me is methyl, Et is ethyl, Pr is n-propyl, and Nit is nitro.
  • Ar is a polynuclear fused-ring aromatic moiety, it can be represented by the general formula wherein ar, Q and m are as defined hereinabove, m' is 1 to 4 and represent a pair of fusing bonds fusing two rings so as to make two carbon atoms part of the rings of each of two adjacent rings.
  • fused ring aromatic moieties Ar are: etc.
  • Ar is a linked polynuclear aromatic moiety it can be represented by the general formula ar(Lng-ar) w (Q) mw wherein w is an integer of 1 to 20, ar is as described above with the proviso that there are at least 3 unsatisfied (i.e., free) valences in the total of ar groups, Q and m are as defined hereinbefore, and each Lng is a bridging linkage individually chosen from carbon-to-carbon single bonds, ether linkages (e.g.
  • keto linkages sulfide linkages e.g., -S-
  • polysulfide linkages of 2 to 6 sulfur atoms e.g., -S 2 - 6 -
  • sulfonyl linkages e.g., -S(0)-
  • sulfonyl linkages e.g., -S(O) 2 -
  • lower alkylene linkages e.g., -CH 2 -, -CH 2 -CH 2 -, etc.
  • di(lower alkyl)-methylene linkages e.g., CR° 2 -
  • lower alkylene ether linkages e.g., -CH 2 O-, CH 2 O-CH 2 -, -CH 2 -CH 2 O-, -CH 2 CH 2 OCH 2 CH 2 - , etc.
  • lower alkylene sulfide linkages e.g., wherein one or more -O-'s in the lower
  • linked moieties are: etc.
  • Ar moiety is normally a benzene nucleus, lower alkylene bridged benzene nucleus, or a naphthalene nucleus.
  • a typical Ar moiety is a benzene or naphthalene nucleus having 3 to 5 unsatisfied valences, so that one or two of said valences may be satisfied by a hydroxyl group with the remaining unsatisfied valences being, insofar as possible, either ortho or para to a hydroxyl group.
  • Ar is a benzene nucleus having at least 3 unsatisfied valences so that one can be satisfied by a hydroxyl group with the remaining 2 or 3 being either ortho or para to the hydroxyl group.
  • hydrocarbon-based denotes a group having a carbon atom directly attached to the remainder of the molecule and having a predominantly hydrocarbon character within the context of this invention. Therefore, hydrocarbon-based groups can contain up to one non-hydrocarbon radical for every ten carbon atoms provided this non-hydrocarbon radical does not significantly alter the predominantly hydrocarbon character of the group.
  • radicals which include, for example, hydroxyl, halo (especially chloro and fluoro), alkoxyl, alkyl mercapto, alkyl sulfoxy, etc.
  • the hydrocarbon-based groups are purely hydrocarbyl and contain no such non-hydrocarbyl radicals.
  • the hydrocarbon-based groups are substantially saturated.
  • substantially saturated it is meant that the group contains no more than one carbon-to-carbon unsaturated bond for every ten carbon-to-carbon single bonds present. Usually, they contain no more than one carbon-to-carbon non-aromatic unsaturated bond for every 50 carbon-to-carbon bonds present.
  • the amino phenols of the present invention can be prepared by a number of synthetic routes. These routes can vary in the type reactions used and the sequence in which they are employed.
  • an aromatic hydrocarbon such as benzene
  • alkylating agent such as a polymeric olefin
  • This intermediate can then be nitrated, for example, to form polynitro intermediate.
  • the polynitro intermediate can in turn be reduced to a diamine, which can then be diazotized and reacted with water to convert one of the amino groups into a hydroxyl group and provide the desired amino phenol.
  • one of the nitro groups in the polynitro intermediate can be converted to a hydroxyl group through fusion with caustic to provide a hydroxy-nitro alkylated aromatic which can then be reduced to provide the desired amino phenol.
  • Another useful route to the amino phenols of this invention involves the alkylation of a phenol with an olefinic alkylating agent to form an alkylated phenol.
  • This alkylated phenol can then be nitrated to form an intermediate nitro phenol which can be converted to the desired amino phenols by reducing at least some of the nitro groups to amino groups.
  • Aromatic hydroxy compounds can be nitrated with nitric acid, mixtures of nitric acid with acids such as sulfuric acid or boron trifluoride, nitrogen tetraoxide, nitronium tetrafluoroborates and acyl nitrates.
  • nitric acid of a concentration of, for example, 30-90% is a convenient nitrating reagent.
  • Substantially inert liquid diluents and solvents such as acetic or butyric acid can aid in carrying out the reaction by improving reagent contact.
  • Conditions and concentrations for nitrating hydroxy aromatic compounds are also well known in the art.
  • the reaction can be carried out at temperatures of -15°C. to 150°C. Usually nitration is conveniently carried out between 25-75°C.
  • nitrating agent 0.5-4 moles of nitrating agent is used for every mole of aromatic nucleus present in the hydroxy aromatic intermediate to be nitrated. If more than one aromatic nucleus is present in the Ar moiety, the amount of nitrating agent can be increased proportionately according to the number of such nuclei present. For example, a mole of naphthalene-based aromatic intermediate has, for purposes of this invention, the equivalent of two "single ring" aromatic nuclei so that 1-4 moles of nitrating agent would generally be used.
  • nitric acid is used as a nitrating agent usually 1.0 to 3.0 moles per mole of aromatic nucleus is used. Up to a 5-molar excess of nitrating agent (per "single ring" aromatic nucleus) may be used when it is desired to drive the reaction forward or carry it out rapidly.
  • Nitration of a hydroxy aromatic intermediate generally takes 0.25 to 24 hours, though it may be convenient to react the nitration mixture for longer periods, such as 96 hours.
  • Reduction of aromatic nitro compounds to the corresponding amines is also well known. See, for example, the article entitled “Amination by Reduction” in Kirk-Othmer “Encyclopedia of Chemical Technology", Second Edition, Vol. 2, pages 76-99.
  • reductions can be carried out with, for example, hydrogen, carbon monoxide or hydrazine, (or mixtures of same) in the presence of metallic catalysts such as palladium, platinum and its oxides, nickel, copper chromite, etc.
  • Co-catalysts such as alkali or alkaline earth metal hydroxides or amines (including amino phenols) can be used in these catalyzed reductions.
  • Reduction can also be accomplished through the use of reducing metals in the presence of acids, such as hydrochloric acid.
  • Typical reducing metals are zinc, iron and tin; salts of these metals can also be used.
  • Nitro groups can also be reduced in the Zinin reaction, which is discussed in "Organic Reactions", Vol. 20, John Wiley & Sons N.Y., 1973, page 455 et seq.
  • the Zinin reaction involves reduction of a nitro group with divalent negative sulfur compounds, such as alkali metal sulfides, polysulfides and hydrosulfides.
  • the nitro groups can be reduced by electrolytic action; see, for example, the "Amination by Reduction” article, referred to above.
  • the amino phenols of this invention are obtained by reduction of nitro phenols with hydrogen in the presence of a metallic catalyst such as discussed above. This reduction is generally carried out at temperatures of 15°-250°C., typically, 50°-150°C., and hydrogen pressures of 0--2000 psig, typically, 50-250 psig.
  • the reaction time for reduction usually varies between 0.5-50 hours.
  • Substantially inert liquid diluents and solvents, such as ethanol, cyclohexane, etc. can be used to facilitate the reaction.
  • the amino phenol product is obtained by well-known techniques such as distillation, filtration, extraction, and so forth.
  • R 4 is a substantially saturated hydrocarbon-based substituent of at least 10 aliphatic carbon atoms
  • a, b and e are each independently an integer of 1 up to three times the number of aromatic nuclei present in Ar with the proviso that the sum of a, b and e does not exceed the unsatisfied valences of Ar
  • Ar is an aromatic moiety having 0 to 3 optional substituents selected from lower alkyl, lower alkoxyl, halo, or combinations of two or more of said optional substituents; with the proviso that when Ar is a benzene nucleus having only one hydroxyl and one R substituent, the R 4 substituent is ortho or para to said hydroxyl substituent.
  • composition of the present invention comprising components (A) and (B)(I) or (A), (B) and (C) are useful in two-stroke cycle engines.
  • the composition comprises (A) and (B) (I)
  • these components are present in the weight range of 97:3 to 80:20; preferably 95:5 to 85:15 and most preferably from 93:7 to 88:12.
  • the composition comprises (A), (B) and (C)
  • these components are present in the following parts by weight: Component Generally Preferred Most Preferred (A) 70-94 76-94 80-90 (B) 5-18 3-12 5-10 (C) 1-12 1-7.5 3-6
  • the components of this invention are blended together according to the above ranges to effect solution. It is understood that other components beside the above-named components may be present with this two-stroke cycle formulation.
  • This second portion is treated with an additional 127.8 parts of 16 molar nitric acid in 130 parts of water at 25-30°.
  • the reaction mixture is stirred for 1.5 hours and then stripped to 220°/30 tor. Filtration provides an oil solution of the desired intermediate (IA).
  • a mixture of 810 parts of the oil solution of the (IA) intermediate described in Example 1A, 405 parts of isopropyl alcohol and 405 parts of toluene is charged to an appropriately sized autoclave.
  • Platinum oxide catalyst (0.81 part) is added and the autoclave evacuated and purged with nitrogen four times to remove any residual air.
  • Hydrogen is fed to the autoclave at a pressure of 29-55 psig while the content is stirred and heated to 27-92° for a total of thirteen hours. Residual excess hydrogen is removed from the reaction mixture by evacuation and purging with nitrogen four times.
  • the reaction mixture is then filtered through diatomaceous earth and the filtrate stripped to provide an oil solution of the desired amino phenol. This solution contains 0.578% nitrogen.
  • a mixture of 906 parts of an oil solution of an alkyl phenyl sulfonic acid (having an average molecular weight of 450, vapor phase osmometry), 564 parts mineral oil, 600 parts toluene, 98.7 parts magnesium oxide and 120 parts water is blown with carbon dioxide at a temperature of 78--85° for seven hours at a rate of about 3 cubic feet of carbon dioxide per hour.
  • the reaction mixture is constantly agitated throughout the carbonation. After carbonation, the reaction mixture is stripped to 165°/20 tor and the residue filtered.
  • the filtrate is an oil solution of the desired overbased magnesium sulfonate having a metal ratio of about 3.
  • a polyisobutenyl succinic anhydride is prepared by reacting a chlorinated poly(isobutene) (having an average chlorine content of 4.3% and an average of 82 carbon atoms) with maleic anhydride at about 200°.
  • the resulting polyisobutenyl succinic anhydride has a saponification number of 90.
  • the mixture is heated to 115°C. and 125 parts of water is added drop-wise over a period of one hour.
  • the mixture is then allowed to reflux at 150°C. until all the barium oxide is reacted. Stripping and filtration provides a filtrate having a barium content of 4.71%.
  • a mixture of 140 parts of toluene and 400 parts of a polyisobutenyl succinic anhydride (prepared from the poly(isobutene) having a molecular weight of about 850, vapor phase osmometry) having a saponification number of 109 and 63.6 parts of an ethylene amine mixture having an average composition corresponding in stoichiometry to tetraethylene pentamine, is heated to 150°C. while the water/toluene azeotrope is removed. The reaction mixture is then heated to 150°C under reduced pressure until toluene ceases to distill.
  • the residual acylated polyamine has a nitrogen content of 4.7%.
  • a mixture of 140 parts (by weight) of a mineral oil, 174 parts of a poly(isobutene) (molecular weight 1000)-substituted succinic anhydride having a saponification number of 105 and 23 parts of isostearic acid is prepared at 90°C.
  • the reaction is exothermic.
  • the mixture is blown at 225°C. with nitrogen at a rate of 5 pounds per hour for 3 hours whereupon 47 parts of an aqueous distillate is obtained.
  • the mixture is dried at 225°C. for 1 hour, cooled to 110°C. and filtered to provide the desired final product in oil solution.
  • This invention also contemplates the use of other additives in the lubricating oil compositions of this invention.
  • additives include such conventional additive types as anti-oxidants, extreme pressure agents, corrosion-inhibiting agents, pour point depressants, color stabilizing agents, anti-foam agents, and other such additive materials known generally to those skilled in the art of formulating lubricating oil compositions.
  • Dye may be used for identification purposes and to indicate whether a two-stroke cycle fuel contains lubricant.
  • Coupling agents such as organic surfactants are incorporated into some products to provide better component solubilities and improved fuel/lubricant mix water tolerance.
  • Anti-wear and lubricity improvers are used in special applications, such as racing and for very high fuel/lubricant ratios. Scavengers or combustion chamber deposit modifiers are sometimes used to promote better spark plug life and to remove carbon deposits. Halogenated compounds and/or phosphorus- containing materials may be used for this application.
  • Rust and corrosion inhibitors of all types are and may be incorporated into two-stroke cycle oil formulations. Odorants or deodorants are sometimes used for aesthetic reasons.
  • Lubricity agents such as synthetic polymers (e.g., polyisobutene having a number average molecular weight in the range of 500 to 10,000), as measured by vapor phase osmometry or gel permeation chromatography, polyol ether (e.g., poly(oxyethylene-oxypropylene)ethers) and ester oils (e.g., the ester oils described above) can also be used in the oil compositions of this invention.
  • Natural oil fractions such as bright stocks (the relatively viscous products formed during conventional lubricating oil manufacture from petroleum) can also be used for this purpose. They are usually present in the two-stroke cycle oil in the amount of 3 to 20% of the total oil composition.
  • Diluents such as petroleum naphthas or low molecular weight esters boiling at the range of 38-90° (e.g., Stoddard solvent) can also be included in the oil compositions of this invention, typically in an amount of 5 to 25%.
  • diluents When diluents are used it is as a direct replacement for (A), i.e., 10 parts of (A) are replaced with 10 parts of a diluent.
  • Table II describes several illustrative biodegradable two-stroke cycle engine oil lubricant compositions of this invention.
  • DETERGENT-DISPERSANT EXAMPLE NATURAL OIL AMOUNT,pbw EXAMPLE AMOUNT AMINO PHENOL OF EXAMPLE 1 A SUNYL 80 85 6 7.5 7.5 B SUNYL 80 90 6 10.0 --- C HIGH OLEIC CORN OIL 96 2 1.0 3.0 D HIGH OLEIC RAPESEED OIL 96 5 1.0 3.0 E HIGH OLEIC SAFFLOWER OIL 88 6 4.0 8.0
  • the lubricating oil can be directly injected into the intake manifold or crankcase along with the fuel or into the fuel just prior to the time the fuel enters the combustion chamber.
  • the two-stroke cycle lubricants of this invention can be used in this type of engine.
  • two-stroke cycle engine lubricating oils are often added directly to the fuel to form a mixture of oil and fuel which is then introduced into the engine cylinder.
  • Such lubricant-fuel oil mixtures are within the scope of this invention.
  • Such lubricant-fuel blends generally contain per 1 part of oil 15-250 parts fuel, typically they contain 1 part oil to 50-100 parts fuel.
  • the fuels used in two-stroke cycle engines are well known to those skilled in the art and usually contain a major portion of a normally liquid fuel such as hydrocarbonaceous petroleum distillate fuel (e.g., motor gasoline as defined by ASTM Specification D-439-73).
  • a normally liquid fuel such as hydrocarbonaceous petroleum distillate fuel (e.g., motor gasoline as defined by ASTM Specification D-439-73).
  • Such fuels can also contain non-hydrocarbonaceous materials such as alcohols, ethers, organo-nitro compounds and the like (e.g., methanol, ethanol, diethyl ether, methyl ethyl ether, nitromethane) are also within the scope of this invention as are liquid fuels derived from vegetable or mineral sources such as corn, alfalfa, shale and coal.
  • gasoline that is, a mixture of hydrocarbons having an ASTM boiling point of 60°C. at the 10% distillation point to 205°C. at the 90% distillation point.
  • Two-stroke cycle fuels also contain other additives which are well known to those of skill in the art.
  • anti-knock agents such as tetra-alkyl lead compounds, lead scavengers such as halo-alkanes (e.g., ethylene dichloride and ethylene dibromide), octane enhancers such as methyl-t-butyl ether (MTBE), ethyl-t-butyl ether (ETBE) and aromatics such as xylene and toluene, dyes, antioxidants such as 2,6-di-tertiary-butyl-4-methylphenol, rust inhibitors, such as alkylated succinic acids and anhydrides, bacteriostatic agents, gum inhibitors, metal deactivators, demulsifiers, upper cylinder lubricants, anti-icing agents.
  • anti-knock agents such as tetra-alkyl lead compounds
  • lead scavengers such as halo-alkan
  • Concentrates containing the nitrogen-containing soluble compositions of this invention are also within the scope of this invention. These concentrates usually comprise 20 to 80% of one or more of the hereinabove described natural oils and 20 to 80% of one or more nitrogen containing soluble compositions. As will be readily understood by those skilled in the art, such concentrates can also contain one or more of the hereinabove described auxiliary additives of various types.
  • the goal is to have a torque drop less than or equal to the reference (the lower the number, the better the lubrication).
  • a fuel:oil of 150:1 is prepared by adding 100 parts of the product of Example A (oil) to 15,000 parts gasoline (fuel).
  • the torque drop in the Hyundai CE50S is 4.75 and the torque drop of a reference two-stroke cycle formulation at the 150:1 fuel to oil ratio is 6.26.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
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Claims (15)

  1. Une composition organique soluble contenant de l'azote comprenant une combinaison de :
    (A) au moins une huile végétale comprenant un triglycéride de la formule
    Figure 00630001
    où R1, R2 et R3 indépendamment sont des groupes hydrocarbyle aliphatique saturés ou insaturés contenant de 8 à 24 atomes de carbone, où l'huile végétale comprend de l'huile de tournesol riche en acide oléique, de l'huile de carthame riche en acide oléique, de l'huile de mais riche en acide oléique ou de l'huile de colza riche en acide oléique, et a une teneur en acide oléique d'au moins 70 %, et
    (B) (I) un détergent/dispersant comprenant au moins un composé acylé contenant de l'azote ayant un substituant d'au moins 10 atomes de carbone aliphatiques préparé en faisant réagir un agent d'acylation carboxylique avec au moins un composé aminé contenant au moins un groupe -NH, où le composé aminé est une alcoylène polyamine de la formule générale
    Figure 00640001
    où U est un groupe alcoylène de 2 à 10 atomes de carbone, R8 est un atome d'hydrogène et n est un nombre de 1 à 10, cet agent d'acylation étant lié au composé aminé par l'intermédiaire d'une liaison imido, amido, amidine ou acyloxy ammonium.
  2. La composition selon la revendication 1 dans laquelle l'agent d'acylation est un acide mono- ou poly-carboxylique ou un réactif équivalent, contenant un substituant hydrocarbyle aliphatique d'au moins 30 atomes de carbone, où le substituant est formé à partir d'un homo- ou interpolymère d'une l-monooléfine en C2-10 ou de mélanges de tels composés, où l'homo- ou interpolymère est dérivé d'éthylène, de propylène, de 1-butène, d'iso-butène ou de leurs mélanges.
  3. La composition selon la revendication 2, dans laquelle l'agent d'acylation est un mélange d'acides monocarboxyliques gras , ayant des chaínes carbonées droites et ramifiées.
  4. La composition selon l'une quelconque des revendications précédentes, dans laquelle le composé aminé est une éthylène, propylène ou triméthylène polyamine d'au moins 2 à 8 groupes amino ou des mélanges de telles polyamines.
  5. La composition selon l'une quelconque des revendications précédentes dans laquelle le rapport en poids A:B(I) est compris entre 97:3 et 80:20.
  6. Une composition selon la revendication 1, comprenant en outre
       au moins un détergent/dispersant choisi parmi
    (B) (II) au moins un sel neutre ou basique d'un acide organique du soufre, d'un phénol ou d'un acide carboxylique ;
    (B) (III) au moins une amine à substituant hydrocarbyle où le substituant hydrocarbyle est substantiellement aliphatique et contient au moins 12 atomes de carbone, avec la condition que cette amine n'est pas l'amino phénol (C) ; et
    (B) (IV) un produit de condensation azoté d'un phénol, d'un aldéhyde et d'un composé aminé ayant au moins un groupe -NH ; et
    (C) au moins un amino phénol de la formule générale
    Figure 00650001
    où R4 est un substituant à base d'hydrocarbure, substantiellement saturé, d'au moins 10 atomes de carbone aliphatiques et de jusqu'à 750 atomes de carbone aliphatiques ; a, b et c sont chacun indépendamment un nombre entier allant de 1 à trois fois le nombre de noyaux aromatiques présents dans Ar, avec la condition que la somme de a, b et c ne dépasse pas le nombre de valences insaturées de Ar ; et Ar est une portion aromatique ayant 0-3 substituants choisis parmi des substituants alcoyle inférieur, alcoxy inférieur, nitro, halogéno ou des combinaisons de deux ou plus de ces substituants.
  7. La composition selon la revendication 6, dans lequelle R' est un groupe alcoyle ou alcényle où R4 contient 30 à 750 atomes de carbone aliphatiques et est formé à partir d'un homo- ou interpolymère d'oléfines en C2-C12, ces oléfines sont choisies parmi l'éthylène, le propylène, le butylène et leurs mélanges, a, b et c sont chacun 1, il n'y a aucun substituant facultatif attaché à Ar, et Ar est un noyau de benzène.
  8. La composition selon la revendication 6, dans laquelle l'amino phénol est de la formule
    Figure 00660001
    où R5 est un substituant à base d'hydrocarbure substantiellement saturé ayant une moyenne de 30 à 400 atomes de carbone aliphatiques, R6 est choisi parmi les radicaux alcoyle inférieur, alcoxy inférieur, nitro et halogéno ; et z est zéro ou un.
  9. La composition selon l'une quelconque des revendications 6 à 8 dans laquelle le détergent/dispersant (B) (II) est au moins un sel métallique basique d'un acide sulfonique organique ou d'un phénol, où le métal est au moins un métal alcalin ou alcalino-terreux.
  10. La composition selon la revendication 9, dans laquelle le détergent/dispersant est au moins un sulfonate de métal alcalino-terreux, où le sulfonate est un alcoyl-benzène sulfonate dans laquel le groupe alcoyle a au moins 8 atomes de carbone.
  11. La composition selon l'une quelconque des revendications 6 à 10, dans laquelle le détergent/dispersant est (B) (III) au moins une amine à substituant hydrocarbyle où l'amine est une mono-amine de la formule générale AXNR7.
  12. La composition selon la revendication 11, dans laquelle l'amine à substituant hydrocarbyle est une aminohydrocarbyl morpholine à substituant hydrocarbyle de la formule générale
    Figure 00670001
    où R7 est un groupe d'hydrocarbure aliphatique de 30 à 400 atomes de carbone, A est de l'hydrogène, un groupe hydrocarbyle de 1 à 10 atomes de carbone ou hydroxy hydrocarbyle de 1 à 10 atomes de carbone et U est un groupe alcoylène de 2 à 10 atomes de carbone.
  13. La composition selon l'une quelconque des revendications 6 à 12, dans laquelle le détergent/dispersant est (B) (IV) un produit de condensation azoté d'un phénol, d'un aldéhyde et d'un composé aminé ayant au moins un groupe -NH, où le phénol est un phénol alcoyle, le groupe alcoyle ayant au moins 30 atomes de carbone, l'aldéhyde est du formaldéhyde ou un équivalent réactif du formaldéhyde et le composé aminé est de la formule
    Figure 00670002
    où U est groupe alcoylène de 2 à 10 atomes de carbone ; chaque R8 indépendamment -est un atome d'hydrogène, un groupe alcoyle inférieur ou un groupe hydroxy-alcoyle inférieur, avec la condition qu'au moins un R8 est un atome d'hydrogène, et n est un nombre de 1 à 10.
  14. La composition selon la revendication 13, dans laquelle on forme le produit de condensation en faisant réagir d'abord le phénol avec l'aldéhyde en présence d'un catalyseur alcalin à une température allant jusqu'à 150°C, en neutralisant ensuite le mélange de réaction intermédiaire ainsi formé et en faisant réagir finalement le mélange de réaction intermédiaire neutralisé avec au moins un composé aminé ayant au moins un groupe -NH.
  15. La composition selon l'une quelconque des revendications 6 à 14 comprenant de 70 à 94 parties en poids de (A), de 5 à 18 parties en poids de (B) et de 1 à 12 parties en poids de (C).
EP93305348A 1992-07-09 1993-07-08 Lubrifiant pour cycle deux-temps composé d'une huile végétale et d'un conditionnement d'additifs Expired - Lifetime EP0578495B1 (fr)

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US910960 1992-07-09

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CN (1) CN1033704C (fr)
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CA (1) CA2100030C (fr)
DE (1) DE69318628T2 (fr)
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TW291495B (fr) * 1994-08-03 1996-11-21 Lubrizol Corp
US5658864A (en) * 1995-03-24 1997-08-19 Ethyl Corporation Biodegradable pour point depressants for industrial fluids derived from biodegradable base oils
DE19747854A1 (de) * 1997-10-30 1999-05-12 Fuchs Petrolub Ag Verfahren und Vorrichtung zur Schmierung und gleichzeitigen Kraftstoffversorgung eines pflanzenöl-tauglichen Verbrennungsmotors
CA2225352C (fr) * 1998-01-30 2003-10-21 Nam Fong Han Produit a base vegetale pour remplacer le petrolatum
JP2000080391A (ja) * 1998-09-04 2000-03-21 Showa Shell Sekiyu Kk ２サイクルガソリンエンジン用潤滑油およびそれに用いる希釈剤組成物
GB2416172B (en) * 2004-07-13 2009-04-22 Alan Edwin Jemmett Rapeseed oil lubricant
GB2421028A (en) * 2004-12-08 2006-06-14 Derek Lowe Fuel for two-stroke engines
AU2005316551A1 (en) * 2004-12-14 2006-06-22 C. M. Intellectual Property And Research, Inc. Composition and methods for improved lubrication, pour point, and fuel performance
JP2006274058A (ja) * 2005-03-29 2006-10-12 Nippon Oil Corp 農業又は林業機械用潤滑油
JP4801919B2 (ja) * 2005-03-29 2011-10-26 Ｊｘ日鉱日石エネルギー株式会社 農業又は林業機械用潤滑油
US8778034B2 (en) * 2006-09-14 2014-07-15 Afton Chemical Corporation Biodegradable fuel performance additives
US8671467B2 (en) 2007-11-20 2014-03-18 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence Head protection system
CN101245282B (zh) * 2008-03-25 2011-05-25 佛山市顺德区远茂化工实业有限公司 一种金属拉丝润滑剂
CN104911001B (zh) * 2015-06-05 2018-04-24 广西大学 米勒循环发动机润滑剂组合物
CN113512460B (zh) * 2021-08-13 2022-10-21 福建科恩优路润滑油有限公司 抗磨清洁型车用润滑油及其制备工艺

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BE781636A (fr) * 1972-04-04 1972-07-31 Labofina Sa Compositions lubrifiantes pour moteurs deux-temps.
IN145085B (fr) * 1976-01-28 1978-08-19 Lubrizol Corp
FI66899C (fi) * 1983-02-11 1984-12-10 Kasvisoeljy Vaextolje Ab Oy Smoerjmedel med triglycerider som huvudkomponent
US5155244A (en) * 1990-02-28 1992-10-13 Karlshamns Ab Preparation of antioxidant glyceride derivatives utilizing esterification
ATE210175T1 (de) * 1991-08-09 2001-12-15 Lubrizol Corp Die verwendung von funktionellen flüssigkeiten mit triglyceriden und verschiedenen additiven als traktorschmieröle

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AU670791B2 (en) 1996-08-01
ATE166382T1 (de) 1998-06-15
EP0578495A1 (fr) 1994-01-12
ZA934917B (en) 1994-02-09
DE69318628T2 (de) 1999-02-11
DE69318628D1 (de) 1998-06-25
AU4177893A (en) 1994-01-13
CN1033704C (zh) 1997-01-01
CN1081465A (zh) 1994-02-02
SG48751A1 (en) 1998-05-18
ES2116412T3 (es) 1998-07-16
JPH06200279A (ja) 1994-07-19
CA2100030A1 (fr) 1994-01-10
CA2100030C (fr) 2003-10-21
TW253907B (fr) 1995-08-11

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