EP0578495A1 - Aus einem Pflanzenöl und einer Zusatzkonditionierung zusammengesetztes Zweitaktzyklusschmiermittel - Google Patents

Aus einem Pflanzenöl und einer Zusatzkonditionierung zusammengesetztes Zweitaktzyklusschmiermittel Download PDF

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Publication number
EP0578495A1
EP0578495A1 EP93305348A EP93305348A EP0578495A1 EP 0578495 A1 EP0578495 A1 EP 0578495A1 EP 93305348 A EP93305348 A EP 93305348A EP 93305348 A EP93305348 A EP 93305348A EP 0578495 A1 EP0578495 A1 EP 0578495A1
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Prior art keywords
carbon atoms
group
aliphatic
oil
composition
Prior art date
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Granted
Application number
EP93305348A
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English (en)
French (fr)
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EP0578495B1 (de
Inventor
William Bricker Chamberlin Iii
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Lubrizol Corp
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Lubrizol Corp
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    • 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
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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 about 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 an animal or vegetable oil of a triglyceride of the formula
  • R1, R2 and R3 are hydrocarbyl groups independently containing from about 8 to about 24 carbon atoms.
  • the term "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.
  • the preferred triglycerides are those in which the aliphatic groups represented by R1, R2 and R3 have from about 8 to about 24 carbon atoms.
  • Typical triglycerides employed within the instant invention include coconut oil, safflower oil, high oleic safflower oil, sunflower oil, rapeseed oil, (both high erucic and low erucic), high oleic rapeseed oil, high oleic sunflower oil, cottonseed oil, peanut oil, corn oil, high oleic corn oil, castor oil, meadowfoam oil, lesquerella oil, soybean oil, palm olein, palm kernel oil, sesame oil, vernonia oil, as well as animal oils and fats having the prescribed structure formula (I), such as lard oil and beef tallow. It is preferred that the triglyceride be of a vegetable oil.
  • soybean oil satisfies a parameter of structure (I) wherein R1, R2 and R3 contain from about 8 to 24 carbon atoms, soybean oil contains a mixture of fatty acids of different carbon lengths incorporated into a triglyceride structure.
  • Table I outlines the composition of a few natural oils which are triglycerides.
  • 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, obtained from sunflower (Helianthus sp.) available from SVO Enterprises, Eastlake, Ohio as Sunyl R 70 or Sunyl R 80 high oleic sunflower oil, high oleic corn oil, soybean oil, castor oil, and vernonia oil.
  • Vernonia oil is preferred because it is a naturally occurring epoxidized oil. However, it is also within the scope of this invention to synthetically epoxidize any naturally occurring oil that is not naturally epoxidized.
  • 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%.
  • an epoxidized natural oil is epoxidized soybean oil and one species present of the epoxidized soybean oil is
  • the detergent/dispersant is (B) (I) that is combined with (A). In another embodiment, the detergent/dispersant is selected from the group consisting of (B) (I) through (B) (IV) that is combined with (A) 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 and where this is done it is to be understood that they are incorporated by reference for their disclosures relevant to the subject matter discussed at the point in the specification in which they are identified.
  • a number of acylated, nitrogen-containing compounds having a substituent R9 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 about 30 carbon atoms. A more detailed discussion of R9 occurs later in this specification.
  • 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 R9 in such acylating agents is often of at least about 50 and up to about 400 carbon atoms.
  • the aliphatic substituted R9 is derived from homopolymerized or interpolymerized C2 ⁇ 10 1-olefins or mixtures of both.
  • R9 is derived from ethylene, propylene, butylene and mixtures thereof. Typically, it is derived from polymerized isobutene.
  • amino compounds useful in making these acylated compounds are the following: (1) polyalkylene polyamines of the general formula wherein each R8 is independently a hydrogen atom, a lower alkyl group, a lower hydroxy alkyl group or a C1 ⁇ 12 hydrocarbon-based group, with the proviso that at least one R8 is a hydrogen atom, n is a whole number of 1 to 10 and U is a C2 ⁇ 10 alkylene group, (2) heterocyclic-substituted polyamines of the formula wherein R8 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-R8 group and (3) aromatic polyamines of the general formula Ar(NR82) y Formula V wherein Ar is an aromatic nucleus of 6 to about 20 carbon atoms, each R8 is as defined hereinabove and y is 2 to about 8.
  • polyalkylene polyamines (1) are ethylene diamine, tetra(ethylene)pentamine, tri(trimethylene)tetramine, 1,2-propylene diamine, etc.
  • 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 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 about 50 to about 400 carbon atoms with a mixture of ethylene polyamines having 3 to about 7 amino nitrogen atoms per ethylene polyamine and about 1 to about 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.
  • the poly(isobutene) substituent has between about 50 to about 400 carbon atoms with a mixture of ethylene polyamines having 3 to about 7 amino nitrogen atoms per ethylene polyamine and about 1 to about 6 ethylene units made from condensation of ammonia with ethylene chloride.
  • 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 about 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 which are hereby incorporated by reference for their disclosures in this regard.
  • 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 about 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 about 30 mole percent straight chain acid and about 70 to about 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 chlorostearic 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. These patents are hereby incorporated by reference for their disclosure of fatty acid/polyamine condensates and their use in lubricating oil formulations.
  • 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-(S03) y ] z M b Formula VI [R10 ⁇ (SO3) a ] d M b Formula VII
  • 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 in
  • R10 in Formula VII is an aliphatic radical containing at least about 15 carbon atoms and M is either a metal cation or hydrogen.
  • types of the R10 radical are alkyl, alkenyl, alkoxyalkyl, carboalkoxyalkyl, etc.
  • Specific examples of R10 are groups derived from petrolatum, saturated and unsaturated paraffin wax, and polyolefins, including polymerized C2, C3, C4, C5, C6, etc., olefins containing from about 15 to 7000 or more carbon atoms.
  • the groups T, R, and R10 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
  • 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 about 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.
  • Patents 2,174,110; 2,174,506; 2,174,508; 2,193,824; 2,197,800; 2,202,781; 2,212,786; 2,213,360; 2,228,598; 2,233,676; 2,239,974; 2,263,312; 2,276,090; 2,276,097; 2,315,514; 2,319,121; 2,321,022; 2,333,568; 2,333,788; 2,335,259; 2,337,552; 2,346,568; 2,366,027; 2,374,193; 2,383,319; 3,312,618; 3,471,403; 3,488,284; 3,595,790; and 3,798,012. These are hereby incorporated by reference for their disclosures in this regard.
  • 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 about 400 carbon atoms.
  • 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, stearyl-octahydroindene 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 R11 is an aliphatic hydrocarbon-based group of at least four carbon atoms, and no more than about 400 aliphatic carbon atoms, a is an integer of from one to four, Ar* is a polyvalent aromatic hydrocarbon nucleus of up to about 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 R11 and a are such that there is an average of at least 8 aliphatic carbon atoms provided by the R11 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 R11 groups are usually purely hydrocarbyl groups, preferably groups such as alkyl or alkenyl radicals.
  • R11 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
  • 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 R11, 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 R12 in Formula X is an aliphatic hydrocarbon group containing at least 4 to about 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 R12 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 about 30 to about 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, R13 in Formula XIII is a substantially saturated hydrocarbon based substituent having an average of from 30 to about 400 aliphatic carbon atoms and R14 is selected from the group consisting of 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 which are hereby incorporated by reference for their disclosures in this regard.
  • 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, which is hereby incorporated by reference for its disclosures in this regard.
  • 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. These patents are hereby incorporated by their reference for their disclosure of suitable hydrocarbyl amines for use in the present invention including their method of preparation.
  • the hydrocarbyl amines useful in this invention include monoamines of the general formula AXNR7 .
  • Formula XIV Illustrative of such monoamines are the following: poly(propylene)amine N,N-dimethyl-N-poly(ethylene/propylene)amine (50:50 mole ratio of monomers) poly(isobutene)amine N,N-di(hydroxyethyl)-N-poly(isobutene)amine poly(isobutene/1-butene/2-butene)amine (50:25:25 mole ratio of monomer) N-(2-hydroxypropyl)-N-poly(isobutene)amine N-poly(1-butene)-aniline N-poly(isobutene)-morpholine
  • 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 R7 is an aliphatic hydrocarbon group of from about 30 to about 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.
  • R7 is an aliphatic hydrocarbon group of from about 30 to about 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 about 30 up to about 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 about 30 up to about 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 about 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. These patents are also incorporated by reference for their disclosure of sulfur-containing Mannich condensates.
  • the condensates used in making the compositions of this invention are made from a phenol bearing an alkyl substituent of about 6 to about 400 carbon atoms,more typically, 30 to about 250 carbon atoms.
  • These typical condensates are made from formaldehyde or C2 ⁇ 7 aliphatic aldehyde and an amino compound such as those used in making the acylated nitrogen-containing compounds described under (B) (I).
  • the conditions under which such condensation reactions are carried out are well known to those skilled in the art as evidenced by the above-noted patents. Therefore, these patents are also incorporated by reference for their disclosures relating to reaction conditions.
  • 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. Briefly, 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 about 30 carbon atoms and up to about 400 carbon atoms with a lower aliphatic C1 ⁇ 7 aldehyde or reversible polymer thereof in the presence of an alkaline reagent, such as an alkali metal hydroxide, at a temperature up to about 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 about 30 to about 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.
  • the aromatic moiety, Ar, of Formula I can be a single aromatic nucleus such as a benzene nucleus, a pyridine nucleus, a thiophene nucleus, a l,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 the group consisting of 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 about 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 the group consisting of carbon-to-carbon single bonds, ether linkages (e.g.
  • keto linkages e.g., sulfide linkages (e.g., -S-), polysulfide linkages of 2 to 6 sulfur atoms (e.g., -S2-6-), sulfonyl linkages (e.g., -S(0)-), sulfonyl linkages (e.g., -S(0)2-), lower alkylene linkages (e.g., -CH2-, -CH2-CH2-, etc.), di(lower alkyl)-methylene linkages (e.g., CR°2-), lower alkylene ether linkages (e.g., -CH20-, CH20-CH2-, -CH2-CH20-, -CH2CH20CH2CH2-, etc.), lower alkylene sulfide linkages (e.g., wherein one or more -O-'s in the lower alkylene ether linkages is replaced with an -S- atom), lower alkylene polys
  • 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.
  • the amino phenols of the present invention contain, directly bonded to the aromatic moiety Ar, a substantially saturated monovalent hydrocarbon-based group R9 of at least about 10 aliphatic carbon atoms.
  • This R9 group can have up to about 400 aliphatic carbon atoms. More than one such group can be present, but usually, no more than 2 or 3 such groups are present for each aromatic nucleus in the aromatic moiety Ar.
  • the total number of R9 groups present is indicated by the value for "a" in Formula II.
  • the hydrocarbon-based group has at least about 30, more typically, at least about 50 aliphatic carbon atoms and up to about 750, more typically, up to about 300 aliphatic carbon atoms.
  • the hydrocarbon-based groups R9 are made from homo- or interpolymers (e.g., copolymers, terpolymers) of mono- and di-olefins having 2 to 10 carbon atoms, such as ethylene, propylene, butene-l, isobutene, butadiene, isoprene, l-hexene, l-octene, etc.
  • these olefins are l-monoolefins such as homopolymers of ethylene.
  • the R groups can also be derived from the halogenated (e.g., chlorinated or brominated) analogs of such homo- or interpolymers.
  • the R9 groups can, however, be made from other sources, such as monomeric high molecular weight alkenes (e.g., l-tetracontene) and chlorinated analogs and hydrochlorinated analogs thereof, aliphatic petroleum fractions, particularly paraffin waxes and cracked and chlorinated analogs and hydrochlorinated analogs thereof, white oils, synthetic alkenes such as those produced by the Ziegler-Natta process (e.g., poly(ethylene) greases) and other sources known to those skilled in the art. Any unsaturation in the R9 groups may be reduced or eliminated by hydrogenation according to procedures known in the art before the nitration step described hereafter.
  • monomeric high molecular weight alkenes e.g., l-tetracontene
  • chlorinated analogs and hydrochlorinated analogs thereof aliphatic petroleum fractions, particularly paraffin waxes and cracked and chlorinated analogs and hydrochlorinated analogs thereof, white oils
  • 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 R are purely hydrocarbyl and contain no such non-hydrocarbyl radicals.
  • the hydrocarbon-based groups R9 are substantially saturated. By 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 hydrocarbon-based groups of the amino phenols of this invention are also substantially aliphatic in nature, that is, they contain no more than one non-aliphatic moiety (cycloalkyl, cycloalkenyl or aromatic) group of six or less carbon atoms for every ten carbon atoms in the R group.
  • the R9 groups contain no more than one such non-aliphatic group for every fifty carbon atoms, and in many cases, they contain no such non-aliphatic groups at all; that is, the typical R groups are purely aliphatic.
  • these purely aliphatic R9 groups are alkyl or alkenyl groups.
  • substantially saturated hydrocarbon-based R9 groups are the following: a tetra(propylene) group a tri(isobutene) group a tetracontanyl group a henpentacontanyl group a mixture of poly(ethylene/propylene) groups of about 35 to about 70 carbon atoms a mixture of the oxidatively or mechanically degraded poly(ethylene/propylene) groups of about 35 to about 70 carbon atoms a mixture of poly(propylene/l-hexene) groups of about 80 to about 150 carbon atoms a mixture of poly(isobutene) groups having between 20 and 32 carbon atoms a mixture of poly(isobutene) groups having an average of 50 to 75 carbon atoms
  • a preferred source of the group R9 are poly(isobutene)s obtained by polymerization of a C4 refinery stream having a butene content of 35 to 75 weight percent and isobutene content of 15 to 60 weight percent in the presence of
  • the attachment of the hydrocarbon-based group R9 to the aromatic moiety Ar of the amino phenols of this invention can be accomplished by a number of techniques well known to those skilled in the art.
  • One particularly suitable technique is the Friedel-Crafts reaction, wherein an olefin (e.g., a polymer containing an olefinic bond), or halogenated or hydrohalogenated analog thereof, is reacted with a phenol.
  • the reaction occurs in the presence of a Lewis acid catalyst (e.g., boron trifluoride and its complexes with ethers, phenols, hydrogen fluoride, etc., aluminum chloride, aluminum bromide, zinc dichloride, etc.).
  • a Lewis acid catalyst e.g., boron trifluoride and its complexes with ethers, phenols, hydrogen fluoride, etc., aluminum chloride, aluminum bromide, zinc dichloride, etc.
  • the amino phenols of this invention contain at least one of each of the following substituents: a hydroxyl group, a R9 group as defined above, and a primary amine group, -NH2.
  • substituents a hydroxyl group, a R9 group as defined above, and a primary amine group, -NH2.
  • Each of the foregoing groups must be attached to a carbon atom which is a part of an aromatic nucleus in the Ar moiety. They need not, however, each be attached to the same aromatic ring if more than one aromatic nucleus is present in the Ar moiety.
  • the amino phenols of this invention contain one each of the foregoing substituents (i.e., a, b and c are each 1) and but a single aromatic ring, most preferably benzene.
  • This preferred class of amino phenols can be represented by the formula wherein the R9 group is a substantially saturated hydrocarbon-based group of about 30 to about 400 aliphatic carbon atoms located ortho or para to the hydroxyl group, R6 is a lower alkyl, lower alkoxyl, nitro group or halogen atom and z is O or 1. Usually z is 0 and R9 is a substantially saturated, purely hydrocarbyl aliphatic group. Often it is an alkyl or alkenyl group para to the -OH substituent. Often there is but one amino group, -NH2 in these preferred amino phenols but there can be two.
  • the amino phenol is of the formula wherein R9 is derived from homopolymerized or interpolymerized C2 ⁇ 10 l-olefins and has an average of from about 30 to about 400 aliphatic carbon atoms and R6 and z are as defined above.
  • R9 is derived from ethylene, propylene, butylene and mixtures thereof. Typically, it is derived from polymerized isobutene. Often R9 has at least about 50 aliphatic carbon atoms and z is zero.
  • 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, about 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 about -15°C. to about 150°C. Usually nitration is conveniently carried out between about 25-75°C.
  • nitrating agent about 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 about 1-4 moles of nitrating agent would generally be used.
  • nitric acid is used as a nitrating agent usually about 1.0 to about 3.0 moles per mole of aromatic nucleus is used. Up to about 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 about 15°-250°C., typically, about 50°-150°C., and hydrogen pressures of about 0--2000 psig, typically, about 50-250 psig.
  • the reaction time for reduction usually varies between about 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.
  • R4 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 the group consisting of 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 R4 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.
  • these components are present in the weight range of about 97:3 to about 80:20; preferably 95:5 to about 85:15 and most preferably from about 93:7 to about 88:12.
  • 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 about 500 to about 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 about 3 to about 20% of the total oil composition.
  • Diluents such as petroleum naphthas or low molecular weight esters boiling at the range of about 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. TABLE II 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 SOYBEAN OIL 80 6 10.0 10.0 D HIGH OLEIC CORN OIL 96 2 1.0 3.0 E VERNONIA OIL 89 4 3.5 7.5 F CASTOR OIL 92 3 2.0 6.0 G SOYBEAN OIL 82 5 3.0 15.0 H HIGH OLEIC RAPESEED OIL 96 5 1.0 3.0 I 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 about 15-250 parts fuel, typically they contain 1 part oil to about 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 about 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 and the like.
  • anti-knock agents such as tetra-alkyl lead compounds
  • lead scavengers such as halo
  • An example of a lubricant-fuel composition encompassed by this invention is a blend of motor gasoline and the lubricant blend described above in Example C in ratio (by weight) of 25-200 parts gasoline to 1 part lubricant.
  • Concentrates containing the nitrogen-containing soluble compositions of this invention are also within the scope of this invention. These concentrates usually comprise about 20 to about 80% of one or more of the hereinabove described natural oils and about 20 to about 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 & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Fats And Perfumes (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP93305348A 1992-07-09 1993-07-08 Aus einem Pflanzenöl und einer Zusatzkonditionierung zusammengesetztes Zweitaktzyklusschmiermittel Expired - Lifetime EP0578495B1 (de)

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US910960 1992-07-09

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EP (1) EP0578495B1 (de)
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CN (1) CN1033704C (de)
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CA (1) CA2100030C (de)
DE (1) DE69318628T2 (de)
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0695799A3 (de) * 1994-08-03 1996-04-03 Lubrizol Corp Ein Kombination von einer Schwefelverbindung und Phosphorverbindungen und ihre Verwendung in Schmierölzusammensetzungen, Konzentrate und Schmierfette
EP0735130A1 (de) * 1995-03-24 1996-10-02 Ethyl Corporation Biologisch abbaubare Stockpunkterniedriger für biologisch abbaubares Basisöl abgeleitete industrielle Flüssigkeiten
WO1999023364A1 (de) * 1997-10-30 1999-05-14 Fuchs Petrolub Ag Verfahren und vorrichtung zur schmierung und gleichzeitigen kraftstoffversorgung eines pflanzenöl-tauglichen verbrennungsmotors
MY119684A (en) * 1998-09-04 2005-06-30 Shell Int Research Lubricating oil for two-cycle gasoline engines and diluent composition therefor.
GB2416172A (en) * 2004-07-13 2006-01-18 Alan Edwin Jemmett Rapeseed oil lubricant
WO2006061611A1 (en) * 2004-12-08 2006-06-15 Derek Lowe Low toxicity fuel and lubricant for two-stroke engines
EP1900794A2 (de) * 2006-09-14 2008-03-19 Afton Chemical Corporation Biologisch abbaubare leistungssteigernde Additive für Brennstoffe

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CA2225352C (en) * 1998-01-30 2003-10-21 Nam Fong Han Vegetable derived petroleum jelly replacement
EA200701285A1 (ru) * 2004-12-14 2007-12-28 Си. Эм. ИНТЕЛЛЕКЧУАЛ ПРОПЕРТИ ЭНД РИСЕРЧ, ИНК. Состав и способы для улучшения характеристики смазки, температуры текучести и топлива
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
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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GB1340804A (en) * 1972-04-04 1973-12-19 Labofina Sa Lubricating compositions for two-stroke engines
FR2339666A1 (fr) * 1976-01-28 1977-08-26 Lubrizol Corp Combinaisons amino phenol-detergent/dispersant et combustibles et lubrifiants les contenant
GB2134923A (en) * 1983-02-11 1984-08-22 Kasvioljy Vaxtolje Ab Oy Anhydrous lubricants containing fatty acid triglycericles
WO1991013134A1 (en) * 1990-02-28 1991-09-05 Greene George H Antioxidant glyceride derivatives
WO1993003123A1 (en) * 1991-08-09 1993-02-18 The Lubrizol Corporation Functional fluid with triglycerides, detergent-inhibitor additives and viscosity modifying additives

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GB1340804A (en) * 1972-04-04 1973-12-19 Labofina Sa Lubricating compositions for two-stroke engines
FR2339666A1 (fr) * 1976-01-28 1977-08-26 Lubrizol Corp Combinaisons amino phenol-detergent/dispersant et combustibles et lubrifiants les contenant
GB2134923A (en) * 1983-02-11 1984-08-22 Kasvioljy Vaxtolje Ab Oy Anhydrous lubricants containing fatty acid triglycericles
WO1991013134A1 (en) * 1990-02-28 1991-09-05 Greene George H Antioxidant glyceride derivatives
WO1993003123A1 (en) * 1991-08-09 1993-02-18 The Lubrizol Corporation Functional fluid with triglycerides, detergent-inhibitor additives and viscosity modifying additives

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0695799A3 (de) * 1994-08-03 1996-04-03 Lubrizol Corp Ein Kombination von einer Schwefelverbindung und Phosphorverbindungen und ihre Verwendung in Schmierölzusammensetzungen, Konzentrate und Schmierfette
EP0735130A1 (de) * 1995-03-24 1996-10-02 Ethyl Corporation Biologisch abbaubare Stockpunkterniedriger für biologisch abbaubares Basisöl abgeleitete industrielle Flüssigkeiten
WO1999023364A1 (de) * 1997-10-30 1999-05-14 Fuchs Petrolub Ag Verfahren und vorrichtung zur schmierung und gleichzeitigen kraftstoffversorgung eines pflanzenöl-tauglichen verbrennungsmotors
US6532918B1 (en) 1997-10-30 2003-03-18 Fuchs Petrolub Ag Method and device for lubricating and simultaneously supplying fuel in a vegetable oil-operated combustion engine
MY119684A (en) * 1998-09-04 2005-06-30 Shell Int Research Lubricating oil for two-cycle gasoline engines and diluent composition therefor.
GB2416172A (en) * 2004-07-13 2006-01-18 Alan Edwin Jemmett Rapeseed oil lubricant
GB2416172B (en) * 2004-07-13 2009-04-22 Alan Edwin Jemmett Rapeseed oil lubricant
WO2006061611A1 (en) * 2004-12-08 2006-06-15 Derek Lowe Low toxicity fuel and lubricant for two-stroke engines
EP1900794A2 (de) * 2006-09-14 2008-03-19 Afton Chemical Corporation Biologisch abbaubare leistungssteigernde Additive für Brennstoffe
EP1900794A3 (de) * 2006-09-14 2009-02-11 Afton Chemical Corporation Biologisch abbaubare leistungssteigernde Additive für Brennstoffe
US8778034B2 (en) 2006-09-14 2014-07-15 Afton Chemical Corporation Biodegradable fuel performance additives
US9562498B2 (en) 2006-09-14 2017-02-07 Afton Chemical Corporation Biodegradable fuel performance additives

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CN1081465A (zh) 1994-02-02
CA2100030A1 (en) 1994-01-10
CA2100030C (en) 2003-10-21
ATE166382T1 (de) 1998-06-15
AU4177893A (en) 1994-01-13
TW253907B (de) 1995-08-11
DE69318628D1 (de) 1998-06-25
JPH06200279A (ja) 1994-07-19
ZA934917B (en) 1994-02-09
DE69318628T2 (de) 1999-02-11
EP0578495B1 (de) 1998-05-20
AU670791B2 (en) 1996-08-01
ES2116412T3 (es) 1998-07-16
SG48751A1 (en) 1998-05-18
CN1033704C (zh) 1997-01-01

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