EP0351428B1 - Compositions et lubrifiants et fluides fonctionnels les contenant - Google Patents

Compositions et lubrifiants et fluides fonctionnels les contenant Download PDF

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Publication number
EP0351428B1
EP0351428B1 EP88910283A EP88910283A EP0351428B1 EP 0351428 B1 EP0351428 B1 EP 0351428B1 EP 88910283 A EP88910283 A EP 88910283A EP 88910283 A EP88910283 A EP 88910283A EP 0351428 B1 EP0351428 B1 EP 0351428B1
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EP
European Patent Office
Prior art keywords
groups
formula
acid
group
carbon atoms
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Expired - Lifetime
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EP88910283A
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German (de)
English (en)
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EP0351428A1 (fr
Inventor
Paul E. Adams
James Noel Vinci
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Lubrizol Corp
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Lubrizol Corp
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/40—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms monocarboxylic
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    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/42—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms polycarboxylic
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    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/50—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring monocarboxylic
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    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
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Definitions

  • compositions comprising (A) at least one neutral or basic metal salt or boron-containing neutral or basic metal salt of at least one acidic organic compound, (B) at least one metal deactivator, and (C) at least one sulfur- and/or phosphorus-containing compound.
  • These compositions are useful in providing lubricants and functional fluids with thermal stability and improved anti-wear, extreme-pressure, load-carrying and/or corrosion-inhibiting properties.
  • Zinc-containing hydraulic fluids are widely accepted for numerous applications. These hydraulic fluids typically have excellent thermal stability and anti-wear properties due to the use therein of zinc-containing anti-wear agents. In recent years, however, there has been a growing concern about the accumulation in the workplace and environment of heavy metals such as zinc. This concern has led to a demand for hydraulic fluids containing ashless anti-wear agents. Ashless anti-wear agents are available, but hydraulic fluids based thereon typically lack sufficient thermal stability to be acceptable for many uses.
  • U.S. Patent 4,627,928 discloses the use of basic magnesium salts of substituted aromatic hydroxy carboxylic acids as dispersants, detergents, antioxidants, etc., for lubricants and fuels.
  • compositions prepared by the sulfurization of various organic materials including olefins are known in the art, and lubricants containing these compositions also are known.
  • U.S. Patent 4,191,659 describes the preparation of sulfurized olefinic compounds by the catalytic reaction of sulfur and hydrogen sulfide with olefinic compounds containing from 3 to 30 carbon atoms. The compounds are reported to be useful in lubricating compositions, particularly those prepared for use as industrial gear lubricants.
  • U.S. Patent 4,119,549 describes a similar procedure for sulfurizing olefins utilizing sulfur and hydrogen sulfide followed by removal of low boiling materials from said sulfurized mixture.
  • Sulfur-containing compositions characterized by the presence of at least one cycloaliphatic group with at least two nuclear carbon atoms of one cycloaliphatic group or two nuclear carbon atoms of different cycloaliphatic groups joined together through a divalent sulfur linkage are described in U.S. Reissue Patent Re 27,331.
  • the sulfur linkage contains at least two sulfur atoms, and sulfurized Diels-Alder adducts are illustrative of the compositions disclosed in the reissue patent.
  • the sulfur-containing compositions are useful as extreme pressure and anti-wear additives in various lubricating oils.
  • Dialdehydes containing disulfide groups and represented by the formula wherein both R groups are the same alkyl groups of 1 to 18 carbon atoms and both R1 groups are the same alkyl or aryl groups are described in U.S. Patent 2,580,695. The compounds are reported to be useful as cross-linking agents and as chemical intermediates.
  • Lubricating compositions containing sulfides having the formula wherein R1 is a hydrocarbon group, R2 is hydrogen or a hydrocarbon group, and x is 1 to 2 are described in U.S. Patent 3,296,137.
  • Canadian Patent 1,168,222 discloses the use as additives for lubricants of the combination of (A) at least one benzotriazole or the reaction product of a benzotriazole with at least one aliphatic amine, and (B) at least one sulfurized aliphatic or alicyclic compound containing about 3-30 carbon atoms.
  • This patent indicates that the lubricants can also contain ash-producing detergents exemplified by oil-soluble neutral and basic salts of alkali and alkaline earth metals with sulfonic acids, carboxylic acids or organic phosphorus acids.
  • composition comprising:
  • compositions are useful as additives for lubricants and functional fluids; particularly hydraulic fluids, gear oils, greases and the like.
  • hydrocarbyl denotes a group having a carbon atom directly attached to the remainder of the molecule and having a hydrocarbon or predominantly hydrocarbon character within the context of this invention.
  • hydrocarbyl denotes a group having a carbon atom directly attached to the remainder of the molecule and having a hydrocarbon or predominantly hydrocarbon character within the context of this invention.
  • groups include the following:
  • alkyl-based alkyl-based
  • aryl-based aryl-based
  • hydrocarbon-based has the same meaning and can be used interchangeably with the term hydrocarbyl when referring to molecular groups having a carbon atom attached directly to the remainder of a molecule.
  • lower as used herein in conjunction with terms such as hydrocarbyl, alkyl, alkenyl, alkoxy, and the like, is intended to describe such groups which contain a total of up to 7 carbon atoms.
  • oil-soluble refers to a material that is soluble in mineral oil to the extent of at least about one gram per liter at 25°C.
  • Component (A) is a neutral or basic metal salt, or boron-containing neutral or basic metal salt, of at least one acidic organic compound, the metal in said salt being selected from alkali metals, alkaline-earth metals, zinc, copper, aluminum or a mixture of two or more of said metals.
  • the acidic organic compound from which these salts are derived are one or more carboxylic acids, sulfur-containing acids, phenols, or a mixture of two or more thereof. These acidic organic compounds are discussed in greater detail below.
  • Basic is a term of art which is generic to well known classes of metal salts. These basic metal salts have also been referred to as “overbased”, “superbased”, “hyperbased”, “high-metal containing salts”, and the like. Basic metal salts are characterized by a metal content in excess of that which would be present according to the stoichiometry of the metal and the particular acidic organic compound reacted with the metal, e.g., a sulfonic acid.
  • neutral or "normal” metal salt produced will contain one equivalent of calcium for each equivalent of acid, i.e., Processes for making such neutral and basic metal salts are well known in the art.
  • Neutral salts can be made by heating a mineral oil solution of an acidic organic compound with a stoichiometric equivalent amount of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature above about 50°C and filtering the resulting mass.
  • Basic salts are similarly made with the exception that a stoichiometric excess of the metal is used.
  • a "promoter" in the neutralization step to aid the incorporation of the excess metal can be used in making the basic salts.
  • compounds useful as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance; alcohols such as methanol, 2-propanol, octyl alcohol, cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; and amines such as aniline, phenylenediamine, phenothiazine, phenyl-beta-naphthylamine, and dodecylamine.
  • a particularly effective method for preparing the basic salts comprises mixing the acid organic compound with an excess of a basic metal neutralizing agent and at least one alcohol promoter, and carbonating the mixture at an elevated temperature such as 60-200°C.
  • Component (A) typically has from 100% to 4000%, preferably from 100% to 3000%, more preferably from 100% to 2800%, more preferably from 200% to 1000% of the metal present in the corresponding neutral salt. In an advantageous embodiment, component (A) has from 110% to 4000%, preferably from 110% to 3000%, more preferably from 110% to 2800%, more preferably from 110% to 1000% of the metal present in the corresponding neutral salt.
  • Preferred metals for the salts (A) include lithium, sodium, magnesium, calcium, potassium, barium, aluminum, zinc and copper. Mixtures of two or more of the foregoing metals can be used. Particularly preferred metals are sodium, magnesium, calcium or mixtures of two or more thereof.
  • the carboxylic acids useful in making the salts (A) of the invention may be aliphatic or aromatic, mono-or polycarboxylic acid or acid-producing compounds. These carboxylic acids include lower molecular weight carboxylic acids (e.g., carboxylic acids having up to 18 carbon atoms such as fatty acids having 10 to 18 carbon atoms or tetrapropenyl-substituted succinic anhydride) as well as higher molecular weight carboxylic acids. Throughout this specification and in the appended claims, any reference to carboxylic acids is intended to include the acid-producing derivatives thereof such as anhydrides, esters, acyl halides, lactones and mixtures thereof unless otherwise specifically stated.
  • the carboxylic acids of this invention are preferably oil-soluble and the number of carbon atoms present in the acid is important in contributing to the desired solubility of the salts (A).
  • the number of carbon atoms in the carboxylic acid should be at least 8 carbon atoms, more preferably at least 18 carbon atoms, more preferably at least 30 carbon atoms, more preferably at least 50 carbon atoms.
  • these carboxylic acids do not contain more than 400 carbon atoms per molecule.
  • the carboxylic acid may contain polar substituents provided that the polar substituents are not present in portions sufficiently large to alter significantly the hydrocarbon character of the carboxylic acid.
  • Typical suitable polar substituents include halo, such as chloro and bromo, oxo, oxy, formyl, sulfenyl, sulfinyl, thio, nitro, etc.
  • Such polar substituents if present, preferably do not exceed 10% by weight of the total weight of the hydrocarbon portion of the carboxylic acid, exclusive of the carboxyl groups.
  • the lower molecular weight monocarboxylic acids contemplated for use in this invention include saturated and unsaturated acids.
  • useful acids include dodecanoic acid, palmitic acid, decanoic acid, oleic acid, lauric acid, stearic acid, myristic acid, linoleic acid, linolenic acid, naphthenic acid, chlorostearic acid, tall oil acid, etc.
  • Anhydrides and lower alkyl esters of these acids can also be used. Mixtures of two or more such agents can also be used. An extensive discussion of these acids is found in Kirk-Othmer "Encyclopedia of Chemical Technology" Third Edition, 1978, John Wiley & Sons New York, pp. 814-871.
  • lower molecular weight polycarboxylic acids examples include dicarboxylic acids and derivatives such as sebacic acid, cetyl malonic acid, tetrapropylene-substituted succinic anhydride, etc. Lower alkyl esters of these acids can also be used.
  • R is a hydrocarbyl group of from 8 to 18 carbon atoms.
  • R is an aliphatic or alicyclic hydrocarbyl group with less than 10% of its carbon-to-carbon bonds being unsaturated. Examples of such groups include 4-butylcyclohexyl, di (isobutyl) , decyl, etc.
  • Acid halides of the afore-described lower molecular weight mono- and polycarboxylic acids can be used as lower molecular weight carboxylic acids in this invention. These can be prepared by the reaction of such acids or their anhydrides with halogenating agents such as phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride. Esters of such acids can be prepared simply by the reaction of the acid, acid halide or anhydride with an alcohol or phenolic compound. Particularly useful are the lower alkyl and alkenyl alcohols such as methanol, ethanol, allyl alcohol, propanol, cyclohexanol, etc. Esterification reactions are usually promoted by the use of alkaline catalysts such as sodium hydroxide or alkoxide, or an acidic catalyst such as sulfuric acid or toluene sulfonic acid.
  • alkaline catalysts such as sodium hydroxide or alkoxide
  • the monocarboxylic acids include isoaliphatic acids, i.e., acids having one or more lower acyclic pendant alkyl groups. Such acids often contain a principal chain having from 14 to 20 saturated, aliphatic carbon atoms and at least one but usually no more than four pendant acyclic alkyl groups.
  • the principal chain of the acid is exemplified by groups derived from tetradecane, pentadecane, hexadecane, heptadecane, octadecane, and eicosane.
  • the pendant group is preferably a lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, or other groups having up to 7 carbon atoms.
  • the pendant group may also be a polar-substituted alkyl group such as chloromethyl, bromobutyl, methoxyethyl, or the like, but it preferably contains no more than one polar substituent per group.
  • isoaliphatic acids include 10-methyl-tetradecanoic acid, 11-methyl-pentadecanoic acid, 3-ethyl-hexadecanoic acid, 15-methyl-heptadecanoic acid, 16-methyl-hep-tadecanoic acid, 6-methyl-octadecanoic acid, 8-methyl-octadecanoic acid, 10-methyl-octadecanoic acid, 14-methyl-octadecanoic acid, 16-methyl-octadecanoic acid, 15-ethyl-heptadecanoic acid, 3-chloromethyl-nonadecanoic acid, 7,8,9,10-tetramethyl-octadecanoic acid, and 2,9,10-trimethyl-octadecanoic acid.
  • the isoaliphatic acids include mixtures of branch-chain acids prepared by the isomerization of commercial fatty acids of, for example, 16 to 20 carbon atoms.
  • a useful method involves heating the fatty acid at a temperature above 250°C and a pressure between 200 and 700 psi (1379-4826 kPa), distilling the crude isomerized acid, and hydrogenating the distillate to produce a substantially saturated isomerized acid.
  • the isomerization can be promoted by a catalyst such as mineral clay, diatomaceous earth, aluminum chloride, zinc chloride, ferric chloride, or some other Friedel-Crafts catalyst.
  • the concentration of the catalyst may be as low as 0.01%, but more often from 0.1% to 3% by weight of the isomerization mixture.
  • the unsaturated fatty acids from which the isoaliphatic acids may be derived include oleic acid, linoleic acid, linolenic acid, and commercial fatty acid mixtures such as tall oil acids.
  • these processes involve the reaction of (1) an ethylenically unsaturated carboxylic acid, acid halide, anhydride or ester reactant with (2) an ethylenically unsaturated hydrocarbon containing at least 18 aliphatic carbon atoms or a chlorinated hydrocarbon containing at least 18 aliphatic carbon atoms at a temperature within the range of 100-300°C.
  • the chlorinated hydrocarbon or ethylenically unsaturated hydrocarbon reactant preferably contains at least 20 carbon atoms, more preferably at least 30 carbon atoms, more preferably at least 40 carbon atoms, more preferably at least 50 carbon atoms, and may contain polar substituents, oil-solubilizing pendant groups, and be unsaturated within the general limitations explained hereinabove. It is these hydrocarbon reactants which provide most of the aliphatic carbon atoms present in the acyl moiety of the final products.
  • the carboxylic acid reactant When preparing the higher molecular weight carboxylic acids, the carboxylic acid reactant usually corresponds to the formula R o -(COOH) n , where R o is characterized by the presence of at least one ethylenically unsaturated carbon-to-carbon covalent bond and n is an integer from 1 to 6 and preferably 1 or 2.
  • the acidic reactant can also be the corresponding carboxylic acid halide, anhydride or ester. Ordinarily, the total number of carbon atoms in the acidic reactant will not exceed 20, preferably this number will not exceed 10 and generally will not exceed 6.
  • the acidic reactant will have at least one ethylenic linkage in an alpha, beta-position with respect to at least one carboxyl function.
  • Exemplary acidic reactants are acrylic acid, methacrylic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid, glutaconic acid, chloromaleic acid, aconitic acid, crotonic acid, methylcrotonic acid, sorbic acid, 3-hexenoic acid, 10-decenoic acid, and the like.
  • Preferred acid reactants include acrylic acid, methacrylic acid, maleic acid, and maleic anhydride.
  • the ethylenically unsaturated hydrocarbon reactant and the chlorinated hydrocarbon reactant used in the preparation of these higher molecular weight carboxylic acids are preferably high molecular weight, substantially saturated petroleum fractions and substantially saturated olefin polymers and the corresponding chlorinated products.
  • Polymers and chlorinated polymers derived from mono-olefins having from 2 to 30 carbon atoms are preferred.
  • Especially useful polymers are the polymers of 1-mono-olefins such as ethylene, propene, 1-butene, isobutene, 1-hexene, 1-octene, 2-methyl-1-heptene, 3-cyclohexyl-1-butene, and 2-methyl-5-propyl-1-hexene.
  • Polymers of medial olefins i.e., olefins in which the olefinic linkage is not at the terminal position, likewise are useful. These are exemplified by 2-butene, 3-pentene, and 4-octene.
  • Interpolymers of 1-mono-olefins such as illustrated above with each other and with other interpolymerizable olefinic substances such as aromatic olefins, cyclic olefins, and polyolefins, are also useful sources of the ethylenically unsaturated reactant.
  • Such interpolymers include for example, those prepared by polymerizing isobutene with styrene, isobutene with butadiene, propene with isoprene, propene with isobutene, ethylene with piperylene, isobutene with chloroprene, isobutene with p-methyl-styrene, 1-hexene with 1,3-hexadiene, 1-octene with 1-hexene, 1-heptene with 1-pentene, 3-methyl-1-butene with 1-octene, 3,3-dimethyl-1-pentene with 1-hexene, isobutene with styrene and piperylene, etc.
  • the interpolymers contemplated for use in preparing the carboxylic acids of this invention are preferably substantially aliphatic and substantially saturated, that is, they should contain at least 80% and preferably 95%, on a weight basis, of units derived from aliphatic mono-olefins. Preferably, they will contain no more than 5% olefinic linkages based on the total number of the carbon-to-carbon covalent linkages present.
  • the polymers and chlorinated polymers are obtained by the polymerization of a C4 refinery stream having a butene content of 35% to 75% by weight and an isobutene content of 30% to 60% by weight in the presence of a Lewis acid catalyst such as aluminum chloride or boron trifluoride.
  • a Lewis acid catalyst such as aluminum chloride or boron trifluoride.
  • the chlorinated hydrocarbons and ethylenically unsaturated hydrocarbons used in the preparation of the higher molecular weight carboxylic acids can have number average molecular weights of up to 100,000 or even higher, although preferred higher molecular weight carboxylic acids have molecular weights up to 10,000, more preferably up to 7500, more preferably up to 5000.
  • Preferred higher molecular weight carboxylic acids are those containing hydrocarbyl groups of at least 18 carbon atoms, preferably at least 30 carbon atoms, more preferably at least 40 carbon atoms, more preferably at least 50 carbon atoms.
  • the higher molecular weight carboxylic acids may also be prepared by halogenating a high molecular weight hydrocarbon such as the above-described olefin polymers to produce a polyhalogenated product, converting the polyhalogenated product to a polynitrile, and then hydrolyzing the polynitrile. They may be prepared by oxidation of a high molecular weight polyhydric alochol with potassium permanganate, nitric acid, or a similar oxidizing agent.
  • Another method involves the reaction of an olefin or a polar-substituted hydrocarbon such as a chloropolyisobutene with an unsaturated polycarboxylic acid such as 2-pentene-1,3,5-tricarboxylic acid prepared by dehydration of citric acid.
  • an olefin or a polar-substituted hydrocarbon such as a chloropolyisobutene
  • an unsaturated polycarboxylic acid such as 2-pentene-1,3,5-tricarboxylic acid prepared by dehydration of citric acid.
  • Monocarboxylic acids may be obtained by oxidizing a monoalcohol with potassium permanganate or by reacting a halogenated high molecular weight olefin polymer with a ketene.
  • Another convenient method for preparing monocarboxylic acid involves the reaction of metallic sodium with an acetoacetic ester or a malonic ester of an alkanol to form a sodium derivative of the ester and the subsequent reaction of the sodium derivative with a halogenated high molecular weight hydrocarbon such as brominated wax or brominated polyisobutene.
  • Monocarboxylic and polycarboxylic acids can also be obtained by reacting chlorinated mono- and polycarboxylic acids, anhydrides, acyl halides, and the like with ethylenically unsaturated hydrocarbons or ethylenically unsaturated substituted hydrocarbons such as the polyolefins and substituted polyolefins described hereinbefore in the manner described in U.S. Patent 3,340,281.
  • the monocarboxylic and polycarboxylic acid anhydrides can be obtained by dehydrating the corresponding acids. Dehydration is readily accomplished by heating the acid to a temperature above 70°C, preferably in the presence of a dehydration agent, e.g., acetic anhydride.
  • a dehydration agent e.g., acetic anhydride.
  • Cyclic anhydrides are usually obtained from polycarboxylic acids having acid groups separated by no more than three carbon atoms such as substituted succinic or glutaric acid, whereas linear anhydrides are usually obtained from polycarboxylic acids having the acid groups separated by four or more carbon atoms.
  • the acid halides of the monocarboxylic and polycarboxylic acids can be prepared by the reaction of the acids or their anhydrides with a halogenating agent such as phosphorus tribromide, phosphorus pentachloride, or thionyl chloride.
  • a halogenating agent such as phosphorus tribromide, phosphorus pentachloride, or thionyl chloride.
  • Hydrocarbyl-substituted succinic acids and the anhydride, acid halide and ester derivatives thereof can be prepared by reacting maleic anhydride with a high molecular weight olefin or a chlorinated hydrocarbon such as a chlorinated polyolefin.
  • the reaction involves merely heating the two reactants at a temperature in the range of 100°C to 300°C, preferably, 100°C to 200°C.
  • the product from this reaction is a hydrocarbyl-substituted succinic anhydride wherein the substituent is derived from the olefin or chlorinated hydrocarbon.
  • the product may be hydrogenated to remove all or a portion of any ethylenically unsaturated covalent linkages by standard hydrogenating procedures, if desired.
  • the hydrocarbyl-substituted succinic anhydrides may be hydrolyzed by treatment with water or steam to the corresponding acid and either the anhydride or the acid may be converted to the corresponding acid halide or ester by reacting with a phosphorus halide, phenol or alcohol.
  • R contains at least 18 carbon atoms, more preferably at least 30 carbon atoms, more preferably at least 40 carbon atoms, more preferably at least 50 carbon atoms.
  • the number average molecular weight for R will generally not exceed 100,000, preferably it will not exceed 10,000, more preferably it will not exceed 7500, more preferably it will not exceed 5000.
  • a group of carboxylic acid derivatives that are particularly useful in making the salts (A) of the invention are the lactones represented by the formula wherein in Formula IV, R1, R2, R3, R4, R5 and R6 are each independently H or hydrocarbyl groups of from 1 to about 30 carbon atoms; R2 and R3 can be linked together to form an aliphatic or aromatic ring; and a is a number in the range of zero to 4.
  • lactones represented by the following formula are particularly useful wherein in Formula V, R7 and R8 are aliphatic hydrocarbyl groups of from 1 to 30 carbon atoms, a and b are numbers in the range of zero to 5 with the proviso that the sum of a and b does not exceed 5, and c is a number in the range of zero to 4.
  • R7 and R8 are aliphatic hydrocarbyl groups of from 1 to 30 carbon atoms
  • a and b are numbers in the range of zero to 5 with the proviso that the sum of a and b does not exceed 5
  • c is a number in the range of zero to 4.
  • the procedures for preparing lactones of this type through intramolecular cyclization of hydroxy-containing carboxylic acids accompanied by the elimination of water are well known in the art. Generally, the cyclization is promoted by the presence of materials such as acetic anhydride, and the reaction is effected by heating the mixtures to elevated temperatures such as the reflux temperature while removing volatile
  • a preferred group of carboxylic acids useful in preparing the salts (A) of the present invention are the aromatic carboxylic acids.
  • These acids can be represented by the formula wherein in Formula VI, R is an aliphatic hydrocarbyl group of preferably 4 to 400 carbon atoms, a is a number in the range of zero to 4, Ar is an aromatic group, X1 and X2 are independently sulfur or oxygen, and b is a number in the range of from 1 to 4, with the proviso that the sum of a and b does not exceed the number of unsatisfied valences of Ar.
  • R and a are such that there is an average of at least 8 aliphatic carbon atoms provided by the R groups in each compound represented by Formula VI.
  • the aromatic group Ar in Formula VI may have the same structure as any of the aromatic groups Ar discussed below under the heading "Phenols".
  • Examples of the aromatic groups that are useful herein include the polyvalent aromatic groups derived from benzene, naphthalene, anthracene, phenanthrene, indene, fluorene, biphenyl, and the like.
  • the Ar groups used herein are polyvalent nuclei derived from benzene or naphthalene such as phenylenes and naphthylene, e.g., methylphenylenes, ethoxyphenylenes, nitrophenylenes, isopropylphenylenes, hydroxyphenylenes, mercaptophenylenes, N,N-diethylaminophenylenes, chlorophenylenes, dipropoxynaphthylenes, triethylnaphthylenes, and similar tri-, tetra-, pentavalent nuclei thereof, etc.
  • phenylenes and naphthylene e.g., methylphenylenes, ethoxyphenylenes, nitrophenylenes, isopropylphenylenes, hydroxyphenylenes, mercaptophenylenes, N,N-diethylaminophenylenes, chlorophenylenes
  • Ar groups 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 4 carbon atoms, hydroxy, mercapto, and the like.
  • R groups in Formula VI 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.
  • polymerized olefins such as polychloroprenes, polyethylenes, polypropylenes, polyisobutylenes, ethylene-prop
  • a group of useful carboxylic acids are those of the formula wherein in Formula VII, R, Ar, X1, X2, a and b are as defined in Formula VI, X3 is oxygen or sulfur, and c is a number in the range of 1 to 4, usually 1 to 2, with the proviso that the sum of a, b and c does not exceed the unsatisfied valences of Ar.
  • R is an aliphatic hydrocarbyl group preferably containing from 4 to 400 carbon atoms
  • a is a number in the range of from zero to 4, preferably 1 to 3
  • b is a number in the range of 1 to 4, preferably 1 to 2
  • c is a number in the range of 1 to 4, preferably 1 to 2, and more preferably 1; with the proviso that the sum of a, b and c does not exceed 6.
  • R and a are such that the acid molecules contain at least an average of 12 aliphatic carbon atoms in the aliphatic hydrocarbon substituents per acid molecule.
  • each aliphatic hydrocarbon substituent contains an average of at least 8 carbon atoms per substituent and 1 to 3 substituents per molecule.
  • aromatic carboxylic acids corresponding to Formulae VII and VIII above are well known or can be prepared according to procedures known in the art.
  • Carboxylic acids of the type illustrated by these formulae and processes for preparing their neutral and basic metal salts are well known and disclosed, for example, in U.S. Patents 2,197,832; 2,197,835; 2,252,662; 2,252,664; 2,714,092; 3,410,798; and 3,595,791.
  • the sulfur-containing acids useful in making salts (A) of the invention include the sulfonic, sulfamic, thiosulfonic, sulfinic, sulfenic, partial ester sulfuric, sulfurous and thiosulfuric acids. Generally they are salts of carbocyclic or aliphatic sulfonic acids.
  • the carbocyclic sulfonic acids include the mono- or polynuclear aromatic or cycloaliphatic compounds.
  • the oil-soluble sulfonates can be represented for the most part by the following formulae: R1 a -T-(SO3) b (IX) R2-(SO3) a (X)
  • 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.; R1 is an aliphatic group such as alkyl, alkenyl, alkoxy, alkoxyal
  • R2 is an aliphatic hydrocarbyl group containing at least 15 carbon atoms.
  • R2 are alkyl, alkenyl, alkoxyalkyl, carboalkoxyalkyl, etc.
  • R2 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, R1, and R2 in the above Formulae IX and X 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.
  • a and b are at least 1, and likewise in Formula X, a is at least 1.
  • oil-soluble sulfonic acids within the scope of Formulae IX and X above, and it is to be understood that such examples serve also to illustrate the salts of such sulfonic acids useful in this invention. In other words, for every sulfonic acid enumerated it is intended that the corresponding neutral and basic metal salts thereof are also understood to be illustrated.
  • Such 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 37.8°C (100°F) to 200 seconds at 98.9°C (210°F); petrolatum sulfonic acids; mono- and poly-wax-substituted sulfonic and polysulfonic acids of, e.g., benzene, naphthalene, phenol, diphenyl ether, naphthalene disulfide, diphenylamine, thiophene, alpha-chloronaphthalene, etc.; other substituted sulfonic acids such as alkyl benzene sulfonic acids (where the alkyl group has at least 8 carbons), cetylphenol mono-sulfide sulfonic acids, dicetyl thianthrene disulfonic acids
  • the latter are acids derived from benzene which have been alkylated with propylene tetramers or isobutene trimers to introduce 1, 2, 3, or more branched-chain C12 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, nitroparaffin 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 cyclo
  • the phenols useful in making the salts (A) of the invention can be represented by the formula R a -Ar-(OH) b (XII) wherein in Formula XII, R is a hydrocarbyl group of from 4 to 400 carbon atoms; Ar is an aromatic group; a and b are each independently numbers of at least one, the sum of a and b being in the range of two up to the number of displaceable hydrogens on the aromatic nucleus or nuclei of Ar. Preferably, a and b are independently numbers in the range of 1 to 4, more preferably 1 to 2. R and a are preferably such that there is an average of at least about 8 aliphatic carbon atoms provided by the R groups for each phenol compound represented by Formula XII.
  • phenol is used herein, it is to be understood that this term is not intended to limit the aromatic group of the phenol to benzene. Accordingly, it is to be understood that the aromatic group as represented by "Ar” in Formula XII, as well as elsewhere in other formulae in this specification and in the appended claims, can be mononuclear such as a phenyl, a pyridyl, a thienyl, or polynuclear.
  • the polynuclear groups can be of the fused type wherein an aromatic nucleus is fused at two points to another nucleus such as found in naphthyl, anthranyl, azanaphthyl, etc.
  • the polynuclear group can also be of the linked type wherein at least two nuclei (either mononuclear 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, sulfinyl linkages, sulfonyl linkages, alkylene linkages, alkylidene 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 two aromatic nuclei; for example, a fluorene nucleus having two benzene nuclei linked by both a methylene linkage and a covalent bond.
  • a nucleus may be considered to have three nuclei but only two of them are aromatic.
  • Ar will contain only carbon atoms in the aromatic nuclei per se (plus any 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 and b in Formula XII.
  • the sum of a and b is from 2 to 6.
  • the sum of a and b is from 2 to 10.
  • the sum of a and b is from 2 to 15.
  • the value for the sum of a and b is limited by the fact that it cannot exceed the total number of displaceable hydrogens on the aromatic nucleus or nuclei of Ar.
  • the single ring aromatic nucleus which can be the Ar group 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 4.
  • Halogen atoms include fluorine, chlorine, bromine and iodine atoms; usually, the halogen atoms are fluorine and chlorine atoms.
  • Ar when Ar is a single ring aromatic group include the following: etc., wherein Me is methyl, Et is ethyl, Pr is propyl, and Nit is nitro.
  • Ar is a polynuclear fused-ring aromatic group, 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.
  • Ar when the aromatic group Ar is a linked polynuclear aromatic group 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 two 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., -O-), keto linkages (e.g., sulfide linkages (e.g., -S-), polysulfide linkages of 2 to 6 sulfur atoms (e.g., -S-2 ⁇ 6), sulfinyl linkages (e.g., -S(O)-), sulfonyl linkages (e.g.,
  • one or more of the ar groups in the above-linked aromatic group can be replaced by fused nuclei such as ar ar m'.
  • Ar is a linked polynuclear aromatic group
  • Ar groups are unsubstituted except for the R and -O- groups (and any bridging groups).
  • the Ar group is normally a benzene nucleus, lower alkylene bridged benzene nucleus, or a naphthalene nucleus.
  • R group in Formula XII is a hydrocarbyl group that is directly bonded to the aromatic group Ar.
  • R preferably contains 6 to 80 carbon atoms, preferably 6 to 30 carbon atoms, more preferably 8 to 25 carbon atoms, and advantageously 8 to 15 carbon atoms.
  • R groups include butyl, isobutyl, pentyl, octyl, nonyl, dodecyl, dodecosyl, 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, propylene tetramer and tri(isobutene).
  • polymerized olefins such as polychloroprenes, polyethylenes, polypropylenes, poly
  • the attachment of the hydrocarbyl group R to the aromatic group Ar 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, aluminium chloride, aluminum bromide, zinc dichloride, etc.).
  • a Lewis acid catalyst e.g., boron trifluoride and its complexes with ethers, phenols, hydrogen fluoride, aluminium chloride, aluminum bromide, zinc dichloride, etc.
  • the phenol group of the salt (A) of this invention contains at least one R group, as defined above, and OH.
  • R group as defined above, and OH.
  • Each of the foregoing must be attached to a carbon atom which is a part of an aromatic nucleus in the Ar group. They need not, however, each be attached to the same aromatic ring if more than one aromatic nucleus is present in the Ar group.
  • the boron-containing neutral or basic metal salts (A) of the invention are prepared by the process comprising reacting (1) at least one acidic organic compound or precursor thereof; (2) at least one metal-containing compound selected from alkali metals, alkaline earth metals, zinc, copper, aluminum or a mixture of two or more thereof; (3) at least one boron compound; and (4) at least one promoter.
  • the acid organic compounds are any of the above-discussed carboxylic acids or acid-producing compounds, sulfur-containing acids, or phenols.
  • the acid (1) can also be a mixture of two or more of these.
  • the metal-containing compound (2) is preferably a metal oxide, metal hydroxide, metal halide, metal carbonate or metal borate. It can also be a mixture of two or more of the foregoing.
  • Preferred metals for the metal-containing compounds (2) include lithium, sodium, magnesium, calcium, potassium, barium, aluminum, zinc and copper. Mixtures of two or more of the foregoing metals can be used. Particularly preferred metals are sodium, magnesium, calcium or mixtures of two or more thereof.
  • the boron compounds (3) include boron oxide, boron oxide hydrate, boron trioxide, boron trifluoride, boron tribromide, boron trichloride, boron acids such as boronic acid (i.e., alkyl-B(OH)2 or aryl-B(OH)2), boric acid (i.e., H3BO3), tetraboric acid (i.e., H2B4O7), metaboric acid (i.e., HBO2), boron anhydrides, boron amides and various esters of such boron acids.
  • boronic acid i.e., alkyl-B(OH)2 or aryl-B(OH)2
  • boric acid i.e., H3BO3
  • tetraboric acid i.e., H2B4O7
  • metaboric acid i.e., HBO2
  • boron anhydrides boron amides and
  • complexes of boron trihalide with ethers, organic acids, inorganic acids, or hydrocarbons is a convenient means of introducing the boron reactant into the reaction mixture.
  • Such complexes are known and are exemplified by boron-trifluoride-triethyl ester, boron trifluoride-phosphoric acid, boron trichloride-chloroacetic acid, boron tribromide-dioxane, and boron trifluoride-methyl ethyl ether.
  • boronic acids include methyl boronic acid, phenyl-boronic acid, cyclohexyl boronic acid, p-heptylphenyl boronic acid and dodecyl boronic acid.
  • the boron acid esters include especially mono-, di-, and tri-organic esters of boric acid with alcohols or phenols such as, e.g., methanol, ethanol, isopropanol, cyclohexanol, cyclopentanol, 1-octanol, 2-octanol, dodecanol, behenyl alcohol, oleyl alcohol, stearyl alcohol, benzyl alcohol, 2-butyl cyclohexanol, ethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, 2,4-hexanediol, 1,2-cyclohexanediol, 1,3-octanediol, glycerol, pentaerythritol diethylene glycol, carbitol, Cellosolve, triethylene glycol, tripropylene glycol, phenol, naphthol, p-butylphenol
  • the promoter (4) is a chemical employed to facilitate the incorporation of metal into the basic metal compositions.
  • the chemicals useful as promoters are water, ammonium hydroxide, organic acids of up to 8 carbon atoms, nitric acid, sulfuric acid, hydrochloric acid, metal complexing agents such as alkyl salicylaldoxime, and alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and mono- and polyhydric alcohols of up to 30 carbon atoms.
  • the alcohols include methanol, ethanol, isopropanol, cyclohexanol, dodecanol, decanol, behenyl alcohol, ethylene glycol, diethylene glycol, triethylene glycol, monomethylether of ethylene glycol, trimethylene glycol, hexamethylene glycol, glycerol, pentaerythritol, benzyl alcohol, phenylethyl alcohol, sorbitol, nitropropanol, chloroethanol, aminoethanol, cinnamyl alcohol, allyl alcohol, and the like.
  • the monohydric alcohols having up to about 10 carbon atoms and mixtures of methanol with higher monohydric alcohols.
  • the boron-containing salts (A) are preferably formed by reacting the organic acid (1) with a portion of the metal-containing compound (2) to form a neutral metal salt of an organic acid. Additional metal-containing compound (2) is then added along with the boron compound (3) and promoter (4). The contents are heated to reflux and held at reflux for several hours.
  • Preferred ratios of components (1), (2), (3) and (4) for the above reaction can be determined by the equation (wherein Eqs. means equivalent): This ratio is preferably in the range of about 0.2 to about 3, more preferably 0.5 to 2.
  • one mole of boron is equal to the number of moles of the boron compound (3) times the number of borons present in that boron compound.
  • the number of moles of boron is 3.2 times 1 or 3.2.
  • the number of moles of boron is 2x4 or 8.
  • one equivalent of a metal is equal to the molecular weight of that metal divided by the valence of the metal ion.
  • the above reactions may be carried out in the presence of a substantially inert liquid solvent/diluent medium.
  • This solvent/diluent medium desirably serves to maintain contact of the components and facilitates control of the reaction temperature.
  • suitable solvent/diluent media include aliphatic and aromatic hydrocarbons such as benzene, toluene, naphtha, mineral oil, hexane, chlorinated hydrocarbons such as dichloro-benzene and heptylchloride, and ethers such as methyl n-amylether and n-butylether.
  • the metal-deactivator (B) may be at least one benzotriazole which may be substituted or unsubstituted.
  • suitable compounds are benzotriazole, alkyl-substituted benzotriazole (e.g., tolyltriazole, ethylbenzotriazole, hexylbenzotriazole, octylbenzotriazoles, etc.) aryl-substituted benzotriazole (e.g., phenylbenzotriazoles, etc.) , an alkaryl- or arylalkyl-substituted benzotriazole, and substituted benzotriazoles wherein the substituents may be hydroxy, alkoxy, halo (especially chloro), nitro, carboxy or carbalkoxy.
  • Preferred are benzotriazole and the alkylbenzotriazoles in which the alkyl group contains 1 to 20 carbon atoms and especially 1 to 8 carbon atoms, most
  • the metal deactivator (B) can also be the reaction product of at least one of the above benzotriazoles with at least one amine to form a nitrogen-containing composition.
  • the amine can be one or more monoamines or polyamines. These monoamines and polyamines can be primary amines, secondary amines or tertiary amines.
  • the amines can be aliphatic, cycloaliphatic, aromatic, or heterocyclic, including aliphatic-substituted cycloaliphatic, aliphatic-substituted aromatic, aliphatic-substituted heterocyclic, cycloaliphatic-substituted aliphatic, cycloaliphatic-substituted aromatic, cycloaliphatic-substituted heterocyclic, aromatic-substituted aliphatic, aromatic-substituted cycloaliphatic, aromatic-substituted heterocyclic-substituted alicyclic, and heterocyclic-substituted aromatic amines and may be saturated or unsaturated.
  • the amines may also contain non-hydrocarbon substituents or groups as long as these groups do not significantly interfere with the reaction of the amines with the acylating reagents of this invention.
  • non-hydrocarbon substituents or groups include lower alkoxy, lower alkyl mercapto, nitro, interrupting groups such as -O- and -S- (e.g., as in such groups as -CH2CH2-X-CH2CH2- where X is -O- or -S-).
  • the amine may be characterized by the formula wherein R1, R2 and R3 are each independently hydrogen or hydrocarbyl, amino-substituted hydrocarbyl, hydroxy-substituted hydrocarbyl, alkoxy-substituted hydrocarbyl, amino, carbamyl, thiocarbamyl, guanyl and acylimidoyl groups.
  • the amines ordinarily contain less than 40 carbon atoms in total and usually not more than 20 carbon atoms in total.
  • Aliphatic monoamines include mono-, di- and tri-aliphatic-substituted amines wherein the aliphatic groups can be saturated or unsaturated and straight or branched chain.
  • Such amines include, for example, mono-, di- and tri-alkyl-substituted amines; mono-, di-and tri-alkenyl-substituted amines; and amines having one or more N-alkenyl substituents and one N-alkyl substituents and the like.
  • the total number of carbon atoms in these aliphatic monoamines will, as mentioned before, normally not exceed 40 and usually not exceed 20 carbon atoms.
  • Such monoamines include ethylamine, diethylamine, triethylamine, n-butylamine, di-n-butylamine, tri-n-butylamine, allylamine, isobutylamine, cocoamine, stearylamine, laurylamine, methyllaurylamine, oleylamine, N-methyloctylamine, dodecylamine, octadecylamine, and the like.
  • cycloaliphatic-substituted aliphatic amines examples include 2-(cyclohexyl)ethylamine, benzylamine, phenethylamine, and 3-(furylpropyl)amine.
  • Cycloaliphatic monoamines are those monoamines wherein there is one cycloaliphatic substituent attached directly to the amino nitrogen through a carbon atom in the cyclic ring structure.
  • Examples of cycloaliphatic monoamines include cyclohexylamines, cyclopentylamines, cyclohexenylamines, cyclopentenylamines, N-ethyl-cyclohexylamine, dicyclohexylamines, and the like.
  • Examples of aliphatic-substituted, aromatic-substituted, and heterocyclic-substituted cycloaliphatic monoamines include propyl-substituted cyclohexylamines, phenyl-substituted cyclopentylamines, and pyranyl-substituted cyclohexylamine.
  • Aromatic amines include those monoamines wherein a carbon atom of the aromatic ring structure is attached directly to the amino nitrogen.
  • the aromatic ring will usually be a mononuclear aromatic ring (i.e., one derived from benzene) but can include fused aromatic rings, especially those derived from naphthalene.
  • Examples of aromatic monoamines include aniline, di-(para-methylphenyl)amine, naphthylamine, N-(n-butyl)-aniline, and the like.
  • aliphatic-substituted, cycloaliphatic-substituted, and heterocyclic-substituted aromatic monoamines are para-ethoxyaniline, para-dodecylaniline, cyclohexyl-substituted naphthylamine, and thienyl-substituted aniline.
  • the polyamines include principally alkylene amines conforming for the most part to the formula wherein n is a number preferably less than about 10, each R is independently a hydrogen group or a hydrocarbyl group preferably having up to 30 carbon atoms, and the alkylene group is preferably a lower alkylene group having less than 8 carbon atoms.
  • the alkylene amines include principally methylene amines, ethylene amines, butylene amines, propylene amines, pentylene amines, hexylene amines, heptylene amines, octylene amines, other polymethylene amines.
  • ethylene diamine triethylene tetramine, propylene diamine, decamethylene diamine, octamethylene diamine, di(heptamethylene) triamine, tripropylene tetramine, tetraethylene pentamine, trimethylene diamine, pentaethylene hexamine, di-(trimethylene) triamine.
  • Higher homologues such as are obtained by condensing two or more of the above-illustrated alkylene amines likewise are useful.
  • ethylene amines are especially useful. They are described in some detail under the heading "Ethylene Amines” in Encyclopedia of Chemical Technology, Kirk and Othmer, Vol. 5, pp. 898-905, Interscience Publishers, New York (1950). Such compounds are prepared most conveniently by the reaction of an alkylene chloride with ammonia. The reaction results in the production of somewhat complex mixtures of alkylene amines, including cyclic condensation products such as piperazines. These mixtures find use in the process of this invention. On the other hand, quite satisfactory products may be obtained also by the use of pure alkylene amines.
  • alkylene amine for reasons of economy as well as effectiveness of the products derived therefrom is a mixture of ethylene amines prepared by the reaction of ethylene chloride and ammonia and having a composition which corresponds to that of tetraethylene pentamine.
  • Hydroxyalkyl-substituted alkylene amines i.e., alkylene amines having one or more hydroxyalkyl substituents on the nitrogen atoms, likewise are contemplated for use herein.
  • HIgher homologues such as are obtained by condensation of the above illustrated alkylene amines or hydroxy alkyl-substituted alkylene amines through amino radicals or through hydroxy radicals are likewise useful. It will be appreciated that condensation through amino radicals results in a higher amine accompanied with removal of ammonia and that condensation through the hydroxy radicals results in products containing ether linkages accompanied with removal of water.
  • the metal deactivator (B) can also be the reaction product of at least one of the above benzotriazoles with at least one nitrogen-containing ashless dispersant of the type described below under the heading "Lubricants and Functional Fluids". Particularly preferred are the nitrogen-containing carboxylic dispersants, amine dispersants and Mannich dispersants described below.
  • the benzotriazole-amine and benzotriazole-ashless dispersant reaction products may be prepared by merely blending the reagents and allowing the reaction to proceed.
  • the reaction may be effected in a substantially inert, normally liquid organic diluent (which may be the oil or diluent constituent of the lubricant or concentrate containing the composition of this invention) such as mineral oil, benzene, toluene, xylene, petroleum naphtha, an aliphatic ether or the like, whereupon it may take place at a temperature as low as 15°C.
  • a substantially inert, normally liquid organic diluent such as mineral oil, benzene, toluene, xylene, petroleum naphtha, an aliphatic ether or the like, whereupon it may take place at a temperature as low as 15°C.
  • it is preferred to carry out the reaction at temperatures of up to 160°C, with temperatures in the range of 60°C
  • the proportions of the benzotriazole and amine or ashless dispersant used for the preparation of the reaction products useful as component (B) may vary widely. In general, it is preferred to incorporate as much of the benzotriazole as possible in an oil-dispersible medium and this can be done by using about one equivalent of amine or ashless dispersant per equivalent of benzotriazole.
  • the equivalent weight of the amine or ashless dispersant is its molecular weight divided by the number of basic nitrogen atoms therein, and that of the benzotriazole is its molecular weight divided by the number of triazole rings therein.) In some instances, however, it may be desirable to use more or less than one equivalent of amine or ashless dispersant per equivalent of benzotriazole.
  • benzotriazole-amine and benzotriazole-ashless dispersant reaction products are not known with certainty and are not critical. It is believed, however, that the benzotriazoles are generally more acidic than the amines or ashless dispersants and thus the compositions may comprise amine salts of the benzotriazoles.
  • the phosphorus-containing amides (C-1) comprise at least one compound represented by the formula: wherein in Formula XIII: X1, X2, X3, X4 and X5 are each independently oxygen or sulfur; R1 and R2 are each independently hydrocarbyl groups; R3, R4, R5, R6 and R7 are each independently hydrogen, halogen or hydrocarbyl groups; a and b are independently zero or 1; n is zero or 1; n' is 1, 2 or 3; with the proviso that:
  • X1, X2 and X5 are preferably oxygen.
  • X3 and X4 are preferably sulfur.
  • R1 and R2 are each independently hydrocarbyl groups of from 1 to 50 carbon atoms, more preferably from 1 to 30 carbon atoms, more preferably from 3 to 18 carbon atoms, more preferably from 4 to 8 carbon atoms.
  • R1 and R2 are independently t-butyl, isobutyl, amyl, isooctyl, decyl, dodecyl, eicosyl, 2-pentenyl, dodecenyl, phenyl, naphthyl, alkylphenyl, alkylnaphtyl, phenylalkyl, naphthylalkyl, alkylphenylalkyl, alkylnaphthylalkyl groups, and the like.
  • R3, R4, R5, R6 and R7 are each independently hydrogen or hydrocarbyl groups of 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, more preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms.
  • R3, R4, R5, R6 and R7 are independently hydrogen; alkyl groups of from 1 to 22 carbon atoms; cycloalkyl groups of from 4 to 22 carbon atoms; or aromatic, alkyl substituted aromatic or aromatic-substituted alkyl groups of from 4 to 34 carbon atoms.
  • R is a linking group, it is preferably methylene.
  • R* is preferably an alkylene or alkylidene group of 1 to 28 carbon atoms.
  • the phosphorous-containing amides represented by Formula XIII can be made by various alternative routes.
  • the preparation of these amides involves the reaction of a phosphorous-containing acid reactant having the formula with an acrylamide-type reactant having the formula wherein the various R and X groups are as set forth above in Formula XIII.
  • the reactant (A) is described above under the heading "Phosphorus-Containing Acids".
  • Examples of reactant (B) include acrylamide, methacrylamide wherein R5 is methyl, and crotonamide.
  • the reaction between the reactants (A) and (B) is exothermic and hence only slight heat need be applied thereto.
  • the reaction conveniently can be carried out in an inert atmosphere such as nitrogen at from 25°C to 100°C, with from 70°C to 90°C being preferred.
  • the reaction can be carried out in the presence or absence of a solvent.
  • the reaction takes place in a solvent medium which typically is a hydrocarbon such as toluene, xylene, hexane, heptane, kerosene, fuel oil, an oil of a lubricating viscosity, and the like or a chlorohydrocarbon such as chloroform, carbon tetrachloride, and the like, or an alcohol such as methanol, ethanol, propanol, butanol, 2-ethylhexanol, and the like.
  • the solvent in addition to acting as such, preferably imparts favourable processing characteristics such as controlling the exothermic reaction as well as preventing unwanted side reactions.
  • the reaction time, while dependent upon temperature, is usually as short as one or two hours or less.
  • reaction product XIV is an intermediate. However, it can also serve as an end product for use as the additive (C-1) of the invention. This product is useful in providing lubricants and functional fluids with enhanced load-carrying, extreme pressure, anti-wear and/or corrosion-inhibiting properties.
  • the intermediate reaction product XIV can be coupled in a manner such as described below and/or further reacted in various ways known to those skilled in the art to include other functional groups R8 on the nitrogen atom which groups include -ROH, -ROR, -RSR, wherein R is as defined above with respect to Formula XIII.
  • the preparation of the phosphorus-containing amides XIII involves reacting reactant (A) with a compound having the formula wherein the various R and X groups and n′ are as set forth in Formula XIII.
  • the reaction between the reactants (A) and (D) is exothermic and thus requires only a slight amount of heat. It is preferably carried out in an inert atmosphere at a temperature from 25°C to 100°C with from 70°C to 90°C being preferred.
  • the reaction time is generally short, for example, on the order of less than an hour or two.
  • Hydrocarbon solvents such as toluene, xylene, hexane, heptane, kerosene, fuel oil, an oil of a lubricating viscosity, and the like or chlorinated hydrocarbon such as chloroform, carbon tetrachloride, and the like, or an alcohol such as methanol, ethanol, propanol, butanol, 2-ethylhexanol, and the like, can be used.
  • the various solvents can be removed by stripping under a vacuum and the like.
  • Another alternative method of preparing the phosphorus-containing amides of Formula XIII and especially the coupled compounds set forth hereinabove containing an R6 group is via a displacement reaction.
  • a metal salt of the reactant (A) is used. That is a metal salt according to the following formula is reacted with a compound of the formula wherein X1, X2, X3, X4, X5, R1, R2, R3, R4, R5, R6, R7 and n are the same as set forth above with respect to Formula XIII.
  • M is an alkali metal (e.g., sodium, potassium and the like) or an alkaline-earth metal (e.g., manganese, calcium and the like) or hydrogen, with sodium and potassium being preferred.
  • X6 is a displaceable halogen or carbon group such as Cl, Br, I, tosyl, mesyl, and the like.
  • the reaction between reactants A′ and F proceeds in a manner very similar to that set forth above with regard to the reaction product between reactants (A) and (B). Briefly, the reaction is carried out at a temperature of 10°C to 200°C with from 50°C to 150°C being preferred. An inert atmosphere such as nitrogen is used. Although not required, the reaction can take place in a menstruum.
  • the solvent also renders by-product salts (e.g., KCl, NaCl, NaBr, KBr, etc.) insoluble in the reaction medium and which can be removed by filtration.
  • the amounts of reactants A′ and F are generally equivalent amounts.
  • the resulting product has the formula
  • the reaction product formed by the reaction between reactants (A) and (B) can be coupled by reacting it with a coupling agent (C) which is an aldehyde or ketone (or a reaction synthon equivalent of an aldehyde or ketone) of the formula wherein R9 and R10 are each independently hydrogen, alkyl groups of 1 to 12 carbon atoms, phenyl, or alkyl-substituted phenyl having from 7 to 12 carbon atoms.
  • C is an aldehyde or ketone (or a reaction synthon equivalent of an aldehyde or ketone) of the formula wherein R9 and R10 are each independently hydrogen, alkyl groups of 1 to 12 carbon atoms, phenyl, or alkyl-substituted phenyl having from 7 to 12 carbon atoms.
  • coupling agent (C) is an aldehyde (i.e., R10 is H) having a total of 1 to 3 carbon atoms therein with one carbon atom being preferred.
  • aldehyde and paraformaldehyde are preferred; these can result in methylene and dimethylene ether coupling groups.
  • the coupling reaction preferably takes place in the presence of a strong mineral or organic acid catalyst such as HCl, H2SO4, H4PO4, CH3SO3H, p-toluenesulfonic acid, and the like.
  • the amount of the acid catalyst is generally from 0.3 to 1.5% by weight, preferably from 0.8 to 1.2%, and more preferably from 0.9 to 1.1% by weight based upon the weight of the total product formed. Although lesser amounts of catalyst can be utilized, the reaction is generally slower and a smaller fraction of the desired product is formed.
  • the reaction with coupling agent (C) preferably takes place at an initial temperature of from 80°C to 120°C, more preferably from 80°C to 100°C in an inert atmosphere. The final reaction temperature is generally higher as from 100°C to 150°C and preferably from 125°C to 135°C.
  • reaction between (A) and (B) is preferably carried out using basic catalysts (i.e., NaHCO3, KHCO3, Na2CO3, KCO3, NaOH, KOH, etc.).
  • basic catalysts i.e., NaHCO3, KHCO3, Na2CO3, KCO3, NaOH, KOH, etc.
  • the ratio of reactant (A) and to reactant (B) that is employed is preferably a 1:1 equivalent weight ratio although greater or lesser amounts can be utilized.
  • a 1:1 equivalent weight ratio of the two reactants is preferable in that otherwise a higher acid number is obtained than desired or one of the reactants is wasted.
  • the amount of reaction product formed and reacted with coupling agent (C) is from 0.3 to 3 weight equivalents of reaction product per weight equivalent of said coupling agent (C) with a 1:1 equivalent ratio being preferred.
  • the coupling agent (C) may be a mixture of different couplers and preferably includes paraformaldehyde.
  • the combination of formaldehyde and phosphorus containing amide compound as described above may couple two amides or may result in the formation of a -CH2OH on the nitrogen atom of the amide. Two of such amides with a -CH2OH group thereon may then be reacted to form a coupled amide with the coupling group being Such a coupling reaction may take place during use of such uncoupled compounds which reaction is endothermic. The endothermic reaction may be beneficial to the load-carrying lubricating properties of the overall oil composition.
  • Couplers R8 in Formula XIII when n' is 2 or 3
  • functional groups R8 in Formula XIII when n' is 1
  • R8 in Formula XIII when n' is 1 can be attached to the nitrogen atoms of the phosphorus-containing amides described above by procedures known to those skilled in the art.
  • the nonmetal-containing phosphorus-containing esters (C-2) of the present invention are characterized by the structural formula wherein in Formula XVI, X1, X2, X3 and X4 each are independently oxygen or sulfur; R1 and R2 are each independently hydrocarbyl groups; R3, R4 and R5 are each independently hydrogen or hydrocarbyl groups; R6 is a hydrocarbyl group; and a and b are each independently zero or 1.
  • X1 and X2 are preferably oxygen, and X3 and X4 are preferably sulfur.
  • R1 and R2 are each independently hydrocarbyl groups of from 1 to 50 carbon atoms, more preferably from 1 to 30 carbon atoms, more preferably from 3 to 18 carbon atoms, more preferably from 4 to 8 carbon atoms.
  • R1 and R2 include independently t-butyl, isobutyl, amyl, isooctyl, decyl, dodecyl, eicosyl, 2-pentenyl, dodecenyl, phenyl, naphthyl, alkylphenyl, alkylnaphthyl, phenylalkyl, naphthylalkyl, alkylphenylalkyl, alkylnaphthylalkyl groups, and the like.
  • R3, R4 and R5 are independently hydrogen or hydrocarbyl groups of from 1 to 50 carbon atoms. More preferably, R3, R4 and R5 are independently hydrogen; alkyl groups of from 1 to 22 carbon atoms; cycloalkyl groups of from 4 to 22 carbon atoms; or aromatic, alkyl-substituted aromatic or aromatic-substituted alkyl groups of from 4 to 34 carbon atoms.
  • R6 is preferably an alkyl group of from 1 to 22 carbon atoms; a cycloalkyl group of from 4 to 22 carbon atoms; or an aromatic, alkyl-substituted aromatic or aromatic-substituted alkyl group of from 4 to 34 carbon atoms.
  • R1 and R2 are independently alkyl groups of from 3 to 18 carbon atoms; X1 and X2 are oxygen; X3 and X4 are sulfur; R3, R4 and R5 independently are hydrogen or methyl; and n ⁇ is 1.
  • the phosphorus-containing esters represented by Formula XVI can be prepared by the reaction of the phosphorus-containing acid. with a compound represented by the formula wherein the various R and X groups are as defined with respect to Formula XVI.
  • Reactant (A) is described above under the heading "Phosphorus-Containing Acids”.
  • Reactant (B) may be prepared by the reaction of an alcohol represented by the formula R6OH with an alpha, beta-unsaturated carboxylic acid represented by the formula wherein R3, R4 and R5 are as defined above with respect to Formula XVI.
  • the reaction between reactants (A) and (B) can be carried out by adding over a period of time either reactant (A) or (B) to the other with stirring preferably in the presence of an inert organic solvent, such as benzene, toluene or methylene chloride.
  • the addition is preferably carried out at an elevated temperature, for instance at reflux.
  • the reaction mixture is then refluxed over a further period of time, for instance from 1 to 4 hours.
  • the product is then cooled and neutralized, for instance by washing with aqueous sodium carbonate and then, if desired, with brine.
  • the solvent is then removed by evaporation and then, if desired, the product is steam-distilled.
  • the product may afterwards be purified by conventional techniques, for instance by filtering.
  • the sulfur-coupled dithiocarbamates (C-3) of the present invention are characterized by the structural formula wherein in Formula XVII, R1, R2 and R3 are each independently H or a hydrocarbyl group; R4 is H, OH or a hydrocarbyl group; R5 and R6 are each independently H, a hydrocarbyl group or hydroxyhydrocarbyl group; or R3 and R4 together and/or R5 and R6 together and/or R1 and R3 together and/or R2 and R4 together may form cyclic groups, and x is a number from 1 to 8.
  • the hydrocarbyl groups of R1 through R4 may be straight-chain or branched-chain hydrocarbyl groups.
  • Each of R1 through R6 may independently contain from 1 to 100 carbon atoms, preferably from 1 to 30 carbon atoms.
  • the groups R1 through R4 may be aliphatic or aromatic groups such as alkyl, cycloalkyl, alkaryl, aralkyl or aryl groups.
  • R3 and R4 together and/or R5 and R6 together may be alkylene groups containing from about 4 to 7 carbon atoms.
  • R3 and R4 together with the carbon atom bonded to R3 and R4 in Formula XVII will form a cycloalkyl group
  • R5 and R6, together with the nitrogen atom bonded to R5 and R6 in Formula XVII forms a heterocyclic group.
  • hydrocarbyl groups R1 through R6 include methyl, ethyl, isopropyl, isobutyl, secondary butyl, cyclohexyl, cyclopentyl, octyl, dodecyl, octadecyl, eicosyl, behenyl, triacontonyl, phenyl, naphthyl, phenethyl, octylphenyl, tolyl, xylyl, dioctadecylphenyl, triethylphenyl, chlorophenyl, methoxyphenyl, dibromophenyl, nitrophenyl, 3-chlorohexyl, etc.
  • the sulfur-coupled dithiocarbamate is characterized by the structural formula S x ( ⁇ CH(R3)-CH(R4)S(S)CNR5R6)2 (XVII-A) wherein in Formula XVII-A, x is a number of from 1 to 2, R3 and R4 are hydrogen or a hydrocarbyl group, and R5 and/or R6 are each individually hydrocarbyl groups.
  • the hydrocarbyl groups in Formula XVII-A may be any of the hydrocarbyl groups described above with respect to Formula XVII.
  • R5 and R6 will contain from 1 to 50 carbon atoms
  • R3 and R4 are hydrocarbyl groups containing from 1 to 100 carbon atoms.
  • the dithiocarbamates are characterized by the structural formula wherein in Formula XVII-B, R1, R2, R3, R5, R6 and x are as defined above with respect to Formula XVII.
  • the resulting product is characterized by either Formula XVII or Formula XVII-A or the product is a mixture comprising principally materials characterized by Formulae XVII and XVII-A.
  • the starting material is (ii) an aldehyde or a ketone, the product is characterized primarily by Formula XVII-B.
  • the sulfur halide utilized in the first step (A) may be sulfur monochloride (i.e., S2Cl2), sulfur dichloride, sulfur monobromide, sulfur dibromide, or mixtures of any of the above sulfur halides with elemental sulfur in varying amounts.
  • olefins and olefin mixtures may be used as the starting material in step (A).
  • Olefin mixtures resulting from the oligomerization of ethylene and/or propylene are available at low cost.
  • the olefinic hydrocarbons contain at least one olefinic double bond which is defined as a non-aromatic double bond. That is, the double bond connects two aliphatic carbon atoms.
  • the olefin be a monoolefin and the olefin may be a terminal monoolefinic hydrocarbon; that is, those olefins in which R1 and R3 are hydrogen and R2 and/or R4 are alkyl or aryl.
  • Internal olefinic compounds e.g., where R1 and R2 are alkyl or aryl groups also are useful. Olefinic compounds containing 3 to 100 carbon atoms and more generally from 3 to 30 carbon atoms are particularly desirable.
  • Isobutene, propylene, and their dimers, trimers, tetramers, etc. and mixtures thereof are also useful olefinic compounds.
  • isobutylene, diisobutylene, triisobutylene and tetraisobutylene are particularly desirable because of their availability.
  • the product which is obtained from the reaction of a sulfur halide with one or more of the above-identified olefinic hydrocarbons is a di(halohydrocarbyl)sulfide intermediate produced by the addition of the elements of the sulfur halide to the unsaturated carbon atoms of the olefin.
  • the reaction proceeds on mixing of the olefin and the sulfur halide although the rate of the reaction is increased by elevating the temperature of the mixture.
  • the mixture generally is between -20°C and 120°C until the reaction is completed.
  • the reaction temperature is dictated by the reactivity of the starting olefin and the thermal stability of the reaction product.
  • the olefin can be warmed to the desired temperature whereupon the sulfur halide can be added dropwise, generally in an inert atmosphere at a rate sufficient to maintain the desired temperature.
  • the reaction mixture may be heated for an extended period to complete the reaction.
  • the amount of sulfur halide reacted with the olefinic hydrocarbon generally is a stoichiometric equivalent.
  • a sulfur monohalide utilized as the sulfur halide source, one mole of sulfur monohalide is reacted with two moles of the olefin or olefin mixture.
  • Catalysts or reaction promoters may be utilized although they are generally found to be unnecessary.
  • Examples of such catalysts or promoters include the lower aliphatic amines and aromatic amines, especially tertiary amines.
  • the aldehydes or ketones which may be utilized as a starting material for reaction with a sulfur halide may be characterized by the following formula R1R3CHC(O)R2 wherein R1, R2 and R3 are each individually hydrogen or hydrocarbyl groups as defined above with respect to Formulae XVII, XVII-A or XVII-B.
  • R1, R2 and R3 are each individually hydrogen or hydrocarbyl groups as defined above with respect to Formulae XVII, XVII-A or XVII-B.
  • the aldehydes and ketones may be reacted with sulfur halides such as sulfur monochloride, sulfur dichloride, sulfur monobromide, sulfur dibromide, and mixtures of sulfur halide with elemental sulfur.
  • sulfur halides such as sulfur monochloride, sulfur dichloride, sulfur monobromide, sulfur dibromide, and mixtures of sulfur halide with elemental sulfur.
  • the reaction of an aldehyde or ketone with a sulfur halide may be effected simply by mixing the two reactants at the desired temperature which may range from -30°C to 250°C or higher.
  • a preferred reaction temperature generally is within the range of from 10 to 80°C.
  • the reaction may be carried out in the presence of a diluent or solvent such as benzene, naphtha, hexane, carbon tetrachloride, chloroform, mineral oil, etc.
  • the diluent/solvent facilitates the control of the reaction temperature and a thorough mixing of the the reactants.
  • the relative amounts of the aldehyde or ketone and the sulfur halide may vary over wide ranges. In most instances, the reaction involves two moles of the aldehyde or ketone and one mole of the sulfur halide. In other instances, an excess of either one of the reactants may be used.
  • sulfur compounds which contain more than two sulfur atoms, (e.g., x is an integer from 3-8) these compounds can be obtained by reacting the aldehydes and ketones with a mixture of sulfur halide and sulfur. This is usually accomplished by reacting the sulfur halide and sulfur prior to reaction with the aldehyde or ketone.
  • ketones include dimethylketone, methylethylketone, diethylketone, methylisopropylketone, methylisobutylketone, etc.
  • the sulfur-coupled dithiocarbamates of the present invention are prepared by reacting the above-described sulfur intermediates with a salt of a dithiocarbamate in an amount sufficient to replace the halo groups with dithiocarbamate groups or to react with both carbonyl groups of the dialdehyde or diketone intermediate.
  • the dithiocarbamate salts may be represented by the formula R5R6NC(S)SX wherein R5 and R6 are each individually hydrogen, hydrocarbyl, or hydroxyhydrocarbyl groups and X is an alkali metal, tertiary amine, or other basic material.
  • the salts of the dithiocarbamic acids may be prepared by the reaction of an amine R5R6NH with carbon disulfide in the presence of a base, usually an alkali metal hydroxide, generally, at a molar ratio of 1:1:1.
  • a base usually an alkali metal hydroxide, generally, at a molar ratio of 1:1:1.
  • the base is an alkali metal hydroxide such as sodium or potassium hydroxide, and more generally, sodium hydroxide.
  • the base can be a tertiary amine or in excess of the amine being used on the reaction.
  • the hydrocarbyl or hydroxyhydrocarbyl groups R5 and R6 may contain from 1 to 50 carbon atoms. Preferably, R5 and R6 are lower hydrocarbyl groups. In one embodiment, R5 and R6 are alkylene groups containing from 4 to 7 carbon atoms, and in this embodiment, R5 and R6 together with the nitrogen atom bonded to R5 and R6 will form a heterocyclic group.
  • the heterocyclic group (and the alkylene group) may contain other atoms such as oxygen and sulfur.
  • amines (R5R6NH) used to form the dithiocarbamates include, for example, methylamine, propylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, methylethylamine, methylcyclohexylamine, piperidine, morpholine, dihexylamine, dioctylamine, dicocoamine, methylhydroxyethylamine, di-hydroxyethylamine, piperazine, etc.
  • the metal salts of dithiocarbamates are known in the art and can be prepared readily by one skilled in the art.
  • One method of preparing alkali metal salts of dithiocarbamic acids involves the reaction of an amine, carbon disulfide and an alkali metal hydroxide. Generally, these reactants are mixed and reacted at low temperature such as between about zero and 15°C.
  • an aqueous amine is cooled to zero to 15°C and carbon disulfide is added dropwise, generally in an inert atmosphere before or during the addition of the alkali metal hydroxide.
  • the aqueous amine is cooled whereupon the alkali metal hydroxide is added followed by the carbon disulfide.
  • the salts of dithiocarbamic acids prepared by the above procedure generally are reacted immediately with the sulfur intermediates which have been described above. Solvents may be included to facilitate the reaction, and alcohols have been found to be satisfactory solvents.
  • the reaction between the sulfur intermediate and the dithiocarbamate salts generally is conducted at from ambient temperature to the reflux temperature of the mixture. The reaction is conducted until the reaction is completed which is generally from 5 to 24 hours. At the end of the reaction, the aqueous phase is separated, and the product is recovered from the organic phase.
  • the product of the reaction of the sulfur monohalide with an olefinic hydrocarbon followed by reaction with the dithiocarbamate generally is a mixture of products which can be represented by the structural Formulae XVII or XVII-A.
  • the reaction product also is a mixture in which the major product is believed to be represented by the structural Formula XVII-B. It is not necessary to isolate the various products since the product mixtures are useful in lubricants and functional fluids.
  • the sulfur-coupled dithiocarbamates (C-3) also may be prepared by a process which comprises the steps of
  • any of the olefinic hydrocarbons and salts of dithiocarbamates described above may be utilized in this process.
  • the reaction of a halogen with an olefinic hydrocarbon is well known in the art, and any procedure for effecting the reaction of a halogen with an olefinic hydrocarbon to produce a halogen-containing intermediate can be utilized.
  • the alkali metal sulfide utilized in the second step may be generally represented by the structural formula M2S x wherein M is an alkali metal and x is 1, 2 or 3. Sodium sulfide is preferred as the alkali metal sulfide for reasons of economy and effectiveness.
  • the halogen-containing intermediate is reacted first with the alkali metal sulfide and then with the salt of a dithiocarbamate.
  • the above reactants can be reacted at various ratios, it is generally desired to react four equivalents of the halogen-containing intermediate with one mole of the alkali metal sulfide and two moles of the dithiocarbamate salt.
  • the reactions may be conducted at any convenient temperature such as from ambient temperature up to about 100°C or higher in some instances.
  • the product obtained by this reaction generally will be a mixture which comprises primarily sulfur-coupled dithiocarbamates which are useful in lubricants and functional fluids.
  • R1, R2, R3 and R4 in Formula I are each independently hydrogen or hydrocarbyl group.
  • the hydrocarbyl groups may be aliphatic or aromatic groups such as alkyl, cycloalkyl, alkaryl, aralkyl or aryl groups.
  • R1 and R2 and/or R3 and R4 together may be alkylene groups containing from about 4 to about 7 carbon atoms.
  • R1 and R2 together with the carbon atom bonded to R1 and R2 in Formula I will form a cycloalkyl group.
  • R3 and R4 together with the carbon atom bonded to R3 and R4 will form a cycloalkyl group.
  • R1 and/or R3 may be G1 or G2.
  • the hydrocarbyl groups R1, R2, R3 and R4 usually will contain up to 30 carbon atoms.
  • the hydrocarbyl groups are alkyl groups containing up to 10 carbon atoms.
  • Specific examples of hydrocarbyl groups include methyl, ethyl, isopropyl, isobutyl, secondary butyl, cyclohexyl, cyclopentyl, octyl, dodecyl, octadecyl, eicosyl, behenyl, triacontonyl, phenyl, naphthyl, phenethyl, octyl-phenyl, tolyl, xylyl, dioctadecyl-phenyl, triethyl-phenyl, chloro-phenyl, methoxy-phenyl, dibromo-phenyl, nitrophenyl, 3-chlorohexyl, etc.
  • the sulfur compound (C-4) represented by Formula I may be thia-aldehydes or thia-ketones. That is, G1 and G2 in Formula I are C(O)R groups.
  • Various thia-bisaldehyde compounds are known, and the synthesis of such compounds have been described in the prior art such as in U.S. Patents 3,296,137 and 2,580,695.
  • Thia-aldehydes and thia-ketones are most conveniently prepared by the sulfurization of a suitable aldehyde or ketone such as one having the structural formula R1R2CHC(O)R wherein R1 is hydrogen, hydrocarbyl groups or C(O)R, R2 is hydrogen or a hydrocarbyl group, and R is hydrogen or a hydrocarbyl group.
  • R3 and R4 in Formula I will be the same as R1 and R2, respectively, and both G1 and G2 are C(O)R groups.
  • R1 is C(O)R
  • the sulfurization product contains four C(O)R groups.
  • the sulfurization can be accomplished by reacting the aldehyde or ketone with a sulfur halide such as sulfur monochloride (i.e., S2Cl2), sulfur dichloride, sulfur monobromide, sulfur dibromide, and mixtures of sulfur halide with sulfur flowers in varying amounts.
  • a sulfur halide such as sulfur monochloride (i.e., S2Cl2), sulfur dichloride, sulfur monobromide, sulfur dibromide, and mixtures of sulfur halide with sulfur flowers in varying amounts.
  • the reaction of an aldehyde or ketone with a sulfur halide may be effected simply by mixing the two reactants at the desired temperature which may range from -30°C to 250°C or higher.
  • the preferred reaction temperature generally is within the range of from 10 to 80°C.
  • the reaction may be carried out in the presence of a diluent or solvent such as benzene, naphtha, hexane, carbon tetrachloride, chloroform, mineral oil, etc.
  • the diluent/solvent facilitates the control of the reaction temperature and a thorough mixing of the the reactants.
  • the relative amounts of the aldehyde or ketone and the sulfur halide may vary over wide ranges. In most instances, the reaction involves two moles of the aldehyde or ketone and one mole of the sulfur halide. In other instances, an excess of either one of the reactants may be used.
  • sulfur compounds which contain more than two sulfur atoms, (e.g., x is an integer from 3-8) these compounds can be obtained by reacting the aldehydes with a mixture of sulfur halide and sulfur. Sulfurization products wherein G1 and G2 are different and may be obtained by sulfurizing mixtures of aldehydes and ketones or mixtures of ketones containing different C(O)R groups.
  • thia-aldehydes and thia-ketones include compounds as represented by Formula I wherein G1 and G2 are C(O)R groups, x is 1 to 4 and R1, R2, R3, R4 and R are as follows: R1 R2 R3 R4 R CH3 H CH3 H H CH3 CH3 CH3 CH3 C25 H C2H5 H H CH3C(O)- H CH3C(O)- H CH3 CH3C(O)- H CH3C(O)- H H C2H5 C4H11 C2H5 C4H11 H
  • thia-aldehydes and thia-ketones which can be prepared as described above can be converted to derivatives containing other functional groups which are normally derivable therefrom.
  • a thia-aldehyde or thia-ketone is converted to a derivative through contemporneous conversion of the aldehyde or ketone groups to other terminal groups by chemical reactants and/or reagents.
  • the thia group (S x ) and the R1- R4 groups are inert and remain unchanged in the compound.
  • the thia-bisaldehydes can be converted to hydroxy-acid derivatives wherein one of the aldehyde groups (G1) is converted to a COOH group, and the other aldehyde group (G2) is converted to a CH2OH group.
  • the hydroxy-acid derivatives are obtainable most conveniently by treating the corresponding thia-bisaldehyde with an alkaline reagent such as an alkali metal hydroxide or alkaline earth metal hydroxide, preferably a dilute aqueous solution thereof containing from 5 to 50% by weight of the hydroxide in water.
  • Such alkaline reagents may be sodium hydroxide, potassium hydroxide, lithium hydroxide, barium hydroxide, calcium hydroxide, strontium hydroxide, etc.
  • the hydroxy-acid is isolated from the reaction mixture by acidification with a mineral acid such as hydrochloric acid.
  • the hydroxy-acid derivatives of thia-bisaldehydes can be represented by Formula I-A below. wherein R1, R2, R3, R4 and x are as previously defined.
  • hydroxy-acid derivatives include 6-hydroxy-2,2,5,5-tetramethyl-3,4-dithiahexanoic acid (i.e., conforming to Formula I-A wherein R1, R2, R3 and R4 are methyl and x is 2); 6-hydroxy-2,2-diethyl-5-propyl-5-butyl-3,4-dithiahexanoic acid; 6-hydroxy-2,2,5,5-tetraethyl-3,4-dithiahexanoic acid; etc.
  • 6-hydroxy-2,2,5,5-tetramethyl-3,4-dithiahexanoic acid i.e., conforming to Formula I-A wherein R1, R2, R3 and R4 are methyl and x is 2
  • 6-hydroxy-2,2-diethyl-5-propyl-5-butyl-3,4-dithiahexanoic acid 6-hydroxy-2,2,5,5-tetraethyl-3,4-dithiahexa
  • various other sulfur-containing compounds useful in the present invention can be obtained by the conversion of such hydroxy group and/or the carboxylic group to other polar groups normally derivable thereform.
  • examples of such derivatives include esters formed by esterification of either or both of the hydroxy group and the carboxylic group; amides, imides, and acyl halides formed through the carboxylic group; and lactones formed through intramolecular cyclization of the hydroxy-acid accompanied with the elimination of water.
  • the carboxylic group (COOH) in Formula I-A can be converted to ester groups (COOR) and amide groups (CON(R)2) wherein the R groups may be hydrogen or hydrocarbyl groups containing from 1 to 30 carbon atoms and more generally from 1 to about 10 carbon atoms.
  • R groups include ethyl, propyl, butyl, phenyl, etc.
  • the amines may be monoamines or polyamines. When polyamines are reacted with the thia-aldehydes or thia-ketones [-C(O)R5], cyclic di-imines can be formed.
  • the amines which are reacted with the thia-aldehydes and thia-ketones to form the imines may be characterized by the formula R6NH2 wherein R6 is hydrogen, or hydrocarbyl, or an amino hydrocarbyl group.
  • R6 is hydrogen, or hydrocarbyl, or an amino hydrocarbyl group.
  • the hydrocarbyl groups will contain up to 30 carbon atoms and will more often by aliphatic hydrocarbyl groups containing from 1 to 30 carbon atoms.
  • the hydrocarbyl amines which are useful in preparing the imine derivatives of the present invention are primary hydrocarbyl amines containing from 2 to 30 carbon atoms in the hydrocarbyl group, and more preferably from 4 to 20 carbon atoms in the hydrocarbyl group.
  • the hydrocarbyl group may be saturated or unsaturated.
  • primary saturated amines are the lower alkyl amines such as methyl amine, ethyl amine, n-propyl amine, n-butyl amine, n-amyl amine, n-hexyl amine; those known as aliphatic primary fatty amines and commercially known as "Armeen” primary amines (products available from Armak Chemicals, Chicago, Illinois).
  • Typical fatty amines include alkyl amines such as n-hexylamine, n-octylamine, n-decylamine, n-dodecylamine, n-tetradecylamine, n-pentadecylamine, n-hexadecylamine, n-octadecylamine (stearyl amine), etc.
  • These Armeen primary amines are available in both distilled and technical grades. While the distilled grade will provide a purer reaction product, the desirable amides, imines and imides will form in reactions with the amines of technical grade.
  • mixed fatty amines such as Armak's Armeen-C, Armeen- O, Armeen-OL, Armeen-T, Armeen-HT, Armeen S and Armeen SD.
  • the amine derived products of this invention are those derived from tertiaryaliphatic primary amines having at least 4 carbon atoms in the alkyl group. For the most part, they are derived from alkyl amines having a total of less than 30 carbon atoms in the alkyl group.
  • tertiary aliphatic primary amines are monoamines represented by the formula wherein R is a hydrocarbyl group containing from one to 30 carbon atoms.
  • R is a hydrocarbyl group containing from one to 30 carbon atoms.
  • Such amines are illustrated by tertiary-butyl amine, tertiary-hexyl primary amine, 1-methyl-1-amino-cyclohexane, tertiary-octyl primary amine, tertiary-decyl primary amine, tertiary-dodecyl primary amine, tertiary-tetradecyl primary amine, tertiary-hexadecyl primary amine, tertiary-octadecyl primary amine, tertiary-tetracosanyl primary amine, tertiary-octacosanyl primary amine.
  • amines are also useful for the purposes of this invention.
  • Illustrative of amine mixtures of this type are "Primene 81R” which is a mixture of C11-C14 tertiary alkyl primary amines and "Primene JM-T” which is a similar mixture of C18-C22 tertiary alkyl primary amines (both are available from Rohm and Haas Company).
  • the tertiary alkyl primary amines and methods for their preparation are well known to those of ordinary skill in the art and, therefore, further discussion is unnecessary.
  • the tertiary alkyl primary amine useful for the purposes of this invention and methods for their preparation are described in U.S. Patent 2,945,749.
  • the R6 group may contain one or more olefinic unsaturation depending on the length of the chain, usually no more than one double bond per 10 carbon atoms.
  • Representative amines are dodecenylamine, myristoleylamine, palmitoleylamine, oleylamine and linoleylamine. Such unsaturated amines also are available under the Armeen tradename.
  • the thia-aldehydes and thia-ketones also can be reacted with polyamines.
  • useful polyamines include diamines such as mono- or dialkyl, symmetrical or asymmetrical ethylene diamines, propane diamines (1,2, or 1,3), and polyamine analogs of the above.
  • Suitable commercial fatty polyamines are "Duomeen C” (N-coco-1,3-diaminopropane), “Duomeen S” (N-soya-1,3-diaminopropane), “Duomeen T” (N-tallow-1,3-diaminopropane), or “Duomeen O” (N-oleyl-1,3-diaminopropane).
  • Duomeens are commercially available diamines described in Product Data Bulletin No. 7-10R1 of Armak Chemical Co., Chicago, Illinois.
  • thia-aldehydes and ketones
  • primary amines or polyamines can be carried out by techniques well known to those skilled in the art.
  • the thia-bisaldehyde or ketone is reacted with the amine or polyamine the reaction in a hydrocarbon solvent at an elevated temperature, generally in an atmosphere of nitrogen.
  • the water which is formed is removed such as by distillation.
  • Sulfur compounds characterized by structural Formula I wherein G1 and G2 may be COOR, C ⁇ N and NO2 can be prepared by the reaction of compounds characterized by the structural formula wherein R1 and R2 are as defined above, and G is COOR, C ⁇ N or NO2, or mixtures of different compound represented by Formula I-B with a sulfur halide or a mixture of sulfur halides and sulfur. Generally, about one mole of sulfur halide is reacted with about two moles of the compounds represented by Formula I-B. In one embodiment, R1 also may be G. In such instances, the sulfur compounds which are formed as a result of the reaction with the sulfur halide will contain four G groups which may be the same or different depending upon the starting material.
  • the resulting product contains four ketone groups; when the starting material contains a ketone group and an ester group (e.g., ethylacetoacetate), resulting product contains two ketone groups and two ester groups; and when the starting material contains two ester groups (e.g., diethylmalonate), the product contains four ester groups.
  • ester groups e.g., diethylmalonate
  • Other combinations of functional groups can be introduced into the sulfur products utilized in the present invention and represented by Formula I by selecting various starting materials containing the desired functional groups.
  • Sulfur compounds represented by Formula I wherein G1 and/or G2 and C ⁇ N groups can be prepared by the reaction of compound represented by Formula I-B wherein G is C ⁇ N and R1 and R2 are hydrogen or hydrocarbyl groups.
  • R1 is hydrogen and R2 is a hydrocarbyl group.
  • useful starting materials include, for example, propionitrile, butyronitrile, etc.
  • Compounds of Formula I wherein G1 and G2 are NO2 groups can be prepared by (1) reacting a nitro hydrocarbon R1R2C(H)NO2 with an alkali metal or alkaline earth metal alkoxide to form the salt of the nitro hydrocarbon, and (2) reacting said salt with sulfur monochloride in an inert, anhydrous nonhydroxylic medium to form a bis (1-nitrohydrocarbyl) disulfide.
  • the nitro hydrocarbon is a primary nitro hydrocarbon (R1 is hydrogen and R2 is hydrocarbyl).
  • nitroethane 1-nitropropane
  • 1-nitrobutane 1-nitro-4-methylhexane
  • (2-nitroethyl) benzene etc.
  • alkanol used in obtaining the alkali or alkaline earth metal salt of the starting primary nitro compound is not critical. It is only necessary that it be appropriate for reaction with the metal to form the alkoxide. Because they are easily obtainable and inexpensive, the lower alkanols (i.e., alkanols of 1 to 4 carbon atoms) such as methanol, ethanol and butanol will usually be employed in the synthesis.
  • the medium in which the salt is reacted with S2Cl2 must be inert to both the reactants. It is also essential that the medium be anhydrous and nonhydroxylic for the successful formation of the novel bis(1-nitrohydrocarbyl) disulfides.
  • suitable media are ether, hexane, benzene, dioxane, higher alkyl ethers, etc.
  • temperatures from 0 to 25°C may be used in this step of the process.
  • temperatures in the range of -5 to +15°C may be used.
  • temperatures between 0 to 5°C are used in this step of the process.
  • nitro sulfides useful in the present invention are: bis(1-nitro-2-phenylethyl) disulfide, bis(1-nitrodecyl) disulfide, bis(1-nitrododecyl) disulfide, bis(1-nitro-2-phenyldecyl) disulfide, bis(1-nitro-2-cyclohexylethyl) disulfide, bis(1-nitropentadecyl) disulfide, bis(1-nitro-3-cyclobutylpropyl) disulfide bis(1-nitro-2-naphthylethyl) disulfide, bis(1-nitro-3-p-tolylpropyl) disulfide, bis(1-nitro-2-cyclooctylethy
  • the carboxylic ester-containing sulfur compounds i.e., G1 is COOR
  • G1 is COOR
  • the ester (COOR) can be hydrolyzed to the carboxylic acid (COOH) which can be converted to other esters by reaction with various alcohols or to amides by reaction with various amines including ammonia in primary or secondary amines such as those represented by the formula (R)2NH wherein each R is hydrogen or a hydrocarbyl group.
  • These hydrocarbyl groups may contain from 1 to 30 carbon atoms and more generally will contain from 1 to 10 carbon atoms.
  • R1 and R2 and/or R3 and R4 together may be alkylene groups containing from 4 to 7 carbon atoms.
  • Such derivatives of structural Formula I can be prepared by reacting the appropriately substituted saturated cyclic material with sulfur halides as described above.
  • cyclic starting materials include cyclohexane carboxaldehyde (C6H11CHO), cyclohexane carbonitrile (C6H11CN), cyclohexane carboxamide (C6H11CONH2), cyclohexane carboxylic acid (C6H11COOH), cyclobutane carboxylic acid (C4H7COOH), cycloheptane carboxylic acid (C7H13COOH), cycloheptyl cyanide (C7H13CN), etc.
  • Example 1 illustrates the preparation of a sulfur composition represented by Formula I. Unless otherwise indicated in this example as well as throughout the specification and the appended claims, all parts and percentages are by weight, and all temperatures are in degrees centigrade.
  • Sulfur monochloride (1620 parts, 12 moles) is charged to a 5-liter flask and warmed under nitrogen to a temperature of about 53°C whereupon 1766 parts (24.5 moles) of isobutyraldehyde are added dropwise under nitrogen at a temperature of 53-60°C over a period of about 6.5 hours.
  • the mixture is heated slowly over a period of 6 hours to a temperature of about 100°C while blowing with nitrogen.
  • the mixture is maintained at 100°C with nitrogen blowing for a period of about 6 hours and volatile materials are removed from the reaction vessel.
  • reaction product then is filtered through a filter aid, and the filtrate is the desired product containing 31.4% sulfur (theory, 31.08%).
  • desired reaction product predominantly 2,2′-dithiodiisobutyraldehyde, is recovered in about 95% yield.
  • compositions of the inventive compositions can be mixed in any order using techniques known to those of ordinary skill in the art.
  • the relative weight ratios of components (A):(B):(C) in the compositions of the invention are generally about (1-500):(0.1-10): (1-500).
  • compositions of this invention are useful as additives for lubricants and functional fluids.
  • These compositions can be employed in a wide variety of lubricants and functional fluids based on a wide variety of oils of lubricating viscosity, including natural and synthetic lubricating oils and mixtures thereof.
  • These lubricants and functional fluids include crankcase lubricating oils for spark-ignited and compression-ignited internal combustion engines, including automobile and truck engines, two-cycle engines, aviation piston engines, marine and railroad diesel engines, and the like. They can also be used in gas engines, stationary power engines and turbines and the like.
  • Transmission fluids including both automatic transmission fluids and manual transmission fluids
  • transaxle lubricants including both automatic transmission fluids and manual transmission fluids
  • gear lubricants including both automatic transmission fluids and manual transmission fluids
  • metal-working lubricants including both automatic transmission fluids and manual transmission fluids
  • hydraulic fluids and other lubricating oil and grease compositions can also benefit from the incorporation therein of the compositions of the present invention.
  • Natural oils include animal oils and vegetable oils (e.g., castor oil, lard oil) as well as solvent-refined or acid-refined mineral lubricating oils of the paraffinic, naphthenic, or mixed paraffin-naphthenic types. Oils of lubricating viscosity derived from coal or shale are also useful base oils. Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, etc.
  • polymerized and interpolymerized olefins e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, etc.
  • alkyl benzenes e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di-(2-ethylhexyl) benzenes, etc.
  • polyphenyls e.g., biphenyls, terphenyls, alkylated polyphenyls, etc.
  • Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of known synthetic lubricating oils that can be used. These are exemplified by the oils prepared through polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methyl-polyisopropylene glycol ether having an average molecular weight of about 1000, diphenyl ether of polyethylene glycol having an average molecular weight of 500-1000, diethyl ether of polypropylene glycol having an average molecular weight of 1000-1500, etc.) or mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C3-C8 fatty acid esters, or the C13 oxo acid diester of tetraethylene glycol.
  • the oils prepared through polymerization of ethylene oxide or propylene oxide the
  • Another suitable class of synthetic lubricating oils that can be used comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acids, alkenyl malonic acids, etc.) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, pentaerythritol, etc.).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, lin
  • esters include dibutyl adipate, di(2-ethylhexyl)-sebacate, di-n-hexyl fumerate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethyl-hexanoic acid, and the like.
  • Esters useful as synthetic oils also include those made from C5 to C12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylol propane, pentaerythritol, dipentaerythritol, tripentaerythritol, etc.
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils comprise another class of useful oils. These include tetraethyl-silicate, tetraisopropyl-silicate, tetra-(2-ethylhexyl)-silicate, tetra-(4-methylhexyl)-silicate, tetra(p-tert-butylphenyl)-silicate, hexyl-(4-methyl-2-pentoxy)-di-siloxane, poly(methyl)-siloxanes, poly-(methylphenyl)-siloxanes, etc.
  • liquid esters of phosphorus-containing acid e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decane phosphonic acid, etc.
  • polymeric tetrahydrofurans and the like.
  • Unrefined, refined and rerefined oils (and mixtures of each with each other) of the type disclosed hereinabove can be used in the lubricant and functional fluid compositions of the present invention.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from a retorting operation a petroleum oil obtained directly from distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
  • Refined oils are similar to the unrefined oils except that they have been further treated in one or more purification steps to improve one or more properties.
  • Rerefined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in service. Such rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques directed toward removal of spent additives and oil breakdown products.
  • the lubricants and functional fluids of the present invention contain an effective amount of the composition of this invention sufficient to provide said lubricants and functional fluids with improved anti-wear, load-carrying, extreme pressure (E.P.), and/or corrosion-inhibiting properties.
  • the compositions of the present invention will be employed in such lubricants and functional fluids at a level in the range of 0.02% to 20% by weight, preferably 0.05% to 5% by weight of the total weight of the lubricant or functional fluid.
  • component (A) is employed at a concentration in the range of 0.01% to 5%, more preferably 0.01% to 2%, more preferably 0.01% to 1% by weight based on the total weight of the lubricant or functional fluid.
  • Component (B) is preferably employed at a concentration in the range of 0.001% to 0.1% by weight based on the total weight of the lubricant or functional fluid.
  • Component (C) is preferably employed at a concentration in the range of 0.01% to 5% by weight based on the total weight of the lubricant or functional fluid.
  • the invention also contemplates the use of lubricants and functional fluids containing other additives in addition to the compositions of this invention.
  • additives include, for example, ashless detergents and dispersants, corrosion-inhibiting agents, antioxidants, viscosity improving agents, E.P. agents, pour point depressants, color stabilizers, anti-foam agents, etc.
  • Ashless detergents and dispersants are so called despite the fact that, depending on its constitution, the dispersant may upon combustion yield a non-volatile material such as boric oxide or phosphorus pentoxide; however, it does not ordinarily contain metal and therefore does not yield a metal-containing ash on combustion.
  • a non-volatile material such as boric oxide or phosphorus pentoxide
  • Many types are known in the art, and any of them are suitable for use in the lubricants of this invention.
  • the following are illustrative: (1) Reaction products of carboxylic acids (or derivatives thereof) containing at least 34 and preferably at least 54 carbon atoms with nitrogen containing compounds such as amine, organic hydroxy compounds such as phenols and alcohols, and/or basic inorganic materials.
  • amine dispersants examples thereof are described for example, in the following U.S. Patents: 3,275,554 3,454,555 3,438,757 3,565,804 (3) Reaction products of alkyl phenols in which the alkyl group contains at least about 30 carbon atoms with aldehydes (especially formaldehyde) and amines (especially polyalkylene polyamines), which may be characterized as "Mannich dispersants".
  • aldehydes especially formaldehyde
  • amines especially polyalkylene polyamines
  • Patents are illustrative: 2,459,112 3,442,808 3,591,598 2,962,442 3,448,047 3,600,372 2,984,550 3,454,497 3,634,515 3,036,003 3,459,661 3,649,229 3,166,516 3,461,172 3,697,574 3,236,770 3,493,520 3,725,277 3,355,270 3,539,633 3,725,480 3,368,972 3,558,743 3,726,882 3,413,347 3,586,629 3,980,569 (4) Products obtained by post-treating the carboxylic, amine or Mannich dispersants with such reagents as urea, thiourea, carbon disulfide, aldehydes, ketones, carboxylic acids, hydrocarbon-substituted succinic anhydrides, nitriles, epoxides, boron compounds, phosphorus compounds or the like.
  • reagents as urea,
  • Extreme pressure (E.P.) agents, corrosion-inhibiting agents and antioxidants which may be included in the lubricants and functional fluids of the invention are exemplified by chlorinated aliphatic hydrocarbons such as chlorinated wax; organic sulfides and polysulfides such as benzyl disulfide, bis(chlorobenzyl)disulfide, dibutyl tetrasulfide, sulfurized methyl ester of oleic acid, sulfurized alkylphenol, sulfurized dipentene, and sulfurized terpene; phosphosulfurized hydrocarbons such as the reaction product of a phosphorus sulfide with turpentine or methyl oleate, phosphorus esters including principally dihydrocarbon and trihydrocarbon phosphites such as dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphite, pentylphenyl
  • Zinc dialkylphosphorodithioates are a well known example.
  • pour point depressants are a particularly useful type of additive often included in the lubricants and functional fluids described herein.
  • the use of such pour point depressants in oil-based compositions to improve low temperature properties of oil-based compositions is well known in the art. See, for example, page 8 of "Lubricant Additives" by C.V. Smalheer and R. Kennedy Smith (Lezius-Hiles Co. publishers, Cleveland, Ohio, 1967).
  • pour point depressants examples include polymethacrylates; polyacrylates; polyacrylamides; condensation products of haloparaffin waxes and aromatic compounds; vinyl carboxylate polymers; and terpolymers of dialkylfumarates, vinyl esters of fatty acids and alkyl vinyl ethers.
  • Pour point depressants useful for the purposes of this invention techniques for their preparation and their uses are described in U.S. Patents 2,387,501; 2,015,748; 2,655,479; 1,815,022; 2,191,498; 2,666,746; 2,721,877; 2,721,878; and 3,250,715.
  • Anti-foam agents are used to reduce or prevent the formation of stable foam.
  • Typical anti-foam agents include silicones or organic polymers. Additional anti-foam compositions are described in "Foam Control Agents", by Henry T. Kerner (Noyes Data Corporation, 1976), pages 125-162.
  • Components (A), (B) and (C) of the compositions of this invention can be added directly to the lubricant or functional fluid.
  • they are diluted with a substantially inert, normally liquid organic diluent such as mineral oil, naphtha, benzene, toluene or xylene, to form an additive concentrate.
  • a substantially inert, normally liquid organic diluent such as mineral oil, naphtha, benzene, toluene or xylene.
  • These concentrates usually contain from 10% to 90% by weight of the inventive compositions and may contain, in addition, one or more other additives known in the art or described hereinabove.
  • the remainder of the concentrate is the substantially inert normally liquid diluent.
  • the lubricant compositions of the present invention may be in the form of greases in which any of the above-described oils of lubricating viscosity can be employed as a vehicle.
  • the lubricating oil generally is employed in an amount sufficient to balance the total grease composition and generally, the grease compositions will contain various quantities of thickening agents and other additive components to provide desirable properties.
  • thickening agents can be used in the preparation of the greases of this invention. Included among the thickening agents are alkali and alkaline earth metal soaps of fatty acids and fatty materials having from 12 to 30 carbon atoms. The metals are typified by sodium, lithium, calcium and barium. Examples of fatty materials include stearic acid, hydroxy stearic acid, stearin, oleic acid, palmetic acid, myristic acid, cottonseed oil acids, and hydrogenated fish oils.
  • thickening agents include salt and salt-soap complexes as calcium stearate-acetate (U.S. Patent 2,197,263), barium stearate acetate (U.S. Patent 2,564,561), calcium stearate-caprylate-acetate complexes (U.S. Patent 2,999,065), calcium caprylate-acetate (U.S. Patent 2,999,066), and calcium salts and soaps of low-, intermediate- and high-molecular weight acids and of nut oil acids.
  • salt and salt-soap complexes as calcium stearate-acetate (U.S. Patent 2,197,263), barium stearate acetate (U.S. Patent 2,564,561), calcium stearate-caprylate-acetate complexes (U.S. Patent 2,999,065), calcium caprylate-acetate (U.S. Patent 2,999,066), and calcium salts and soaps of low-, intermediate- and high-molecular weight acids and of
  • Particularly useful thickening agents employed in the grease compositions are essentially hydrophilic in character, but which have been converted into a hydrophobic condition by the introduction of long chain hydrocarbon radicals onto the surface of the clay particles prior to their use as a component of a grease composition, as, for example, by being subjected to a preliminary treatment with an organic cationic surface-active agent, such as an onium compound.
  • organic cationic surface-active agent such as an onium compound.
  • Typical onium compounds are tetraalkylammonium chlorides, such as dimethyl dioctadecyl ammonium chloride, dimethyl dibenzyl ammonium chloride and mixtures thereof. This method of conversion, being well known to those skilled in the art, and is believed to require no further discussion.
  • the clays which are useful as starting materials in forming the thickening agents to be employed in the grease compositions can comprise the naturally occurring chemically unmodified clays.
  • These clays are crystalline complex silicates, the exact composition of which is not subject to precise description, since they vary widely from one natural source to another.
  • These clays can be described as complex inorganic silicates such as aluminum silicates, magnesium silicates, barium silicates, and the like, containing, in addition to the silicate lattice, varying amounts of cation-exchangeable groups such as sodium.
  • Hydrophilic clays which are particularly useful for conversion to desired thickening agents include montmorillonite clays, such as bentonite, attapulgite, hectorite, illite, saponite, sepiolite, biotite, vermiculite, zeolite clays, and the like.
  • the thickening agent is employed in an amount from 0.5 to 30, and preferably from 3% to 15% by weight of the total grease composition.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (15)

  1. Une composition comportant :
    (A) au moins un sel métallique neutre ou basique, ou bien un sel métallique, neutre ou basique, renfermant du bore, d'au moins un composé acide organique choisi parmi un ou plus d'un acide carboxylique, d'acides renfermant du soufre, de phénols ou d'un mélange de deux ou de plus de deux de ceux-ci, le métal dans ledit sel étant choisi parmi un métal alcalin, un métal alcalino-terreux, le zinc, le cuivre, l'aluminium ou un mélange de deux ou de plus de deux de ces métaux ;
    (B) au moins un désactivateur métallique choisi parmi le benzotriazole, un benzotriazole à substitution alkyle, aryle, alkaryle ou arylalkyle, un benzotriazole à substitution hydroxy, alcoxy, halo, nitro, carboxy ou carbalcoxy, le produit de réaction d'au moins un desdits benzotriazoles et d'au moins une amine, le produit de réaction d'au moins un desdits benzotriazoles et d'au moins un agent dispersant sans cendre renfermant de l'azote, un mélange de deux ou de plus de deux de ceux-ci, et
    (C) au moins un composé choisi parmi :
    (C-1) un amide renfermant du phosphore représenté par la formule :
    Figure imgb0087
     formule XIII dans laquelle :
    X¹, X², X³, X⁴ et X⁵ représentent chacun de façon indépendante de l'oxygène ou du soufre ;
    R¹ et R² représentent chacun de façon indépendante des groupes hydrocarbyle ;
    R³, R⁴, R⁵, R⁶ et R⁷ représentent chacun de façon indépendante de l'hydrogène, de l'halogène ou des groupes hydrocarbyle ;
    a et b représentent chacun de façon indépendante 0 ou 1 n est zéro ou 1 ;
    n' est 1, 2 ou 3 ;
    sous la condition que :
    (1) lorsque n' est 1, R⁸ est de l'hydrogène, -R, -ROH, -ROR, -RSR ou
    Figure imgb0088
    (2) lorsque n' est 2, R⁸ est un groupe de couplage choisi parmi -R-, -R*-, -R-O-R-, -R-S-R-,
    Figure imgb0089
     et
    (3) lorsque n' est 3, R⁸ est le groupe de couplage
    Figure imgb0090
     où chaque R représente de façon indépendante un groupe hydrocarbyle de 1 à 12 atomes de carbone ; et R* est un groupe hydrocarbyle ou carboxyhydrocarbyle de 1 à 60 atomes de carbone ;
    (C-2) un ester renfermant du phosphore, nonmétallique, représenté par la formule :
    Figure imgb0091
     formule XVI dans laquelle, X¹, X², X³ et X⁴ représentent chacun de façon indépendante de l'oxygène et du soufre ;
       R¹ et R² sont chacun indépendamment des groupes hydrocarbyle ;
       R³, R⁴, et R⁵ sont chacun, de façon indépendante, de l'hydrogène ou des groupes hydrocarbyle ;
       R⁶ est un groupe hydrocarbyle et
       a et b représentent chacun, de façon indépendante, 0 ou 1 ;
    (C-3) un dithiocarbamate couplé à du soufre, représenté par la formule
    Figure imgb0092
     formule XVII dans laquelle, R¹, R² et R³ sont chacun, de façon indépendante, H ou un groupe hydrocarbyle ; R⁴ est H, OH ou un groupe hydrocarbyle ; R⁵ et R⁶ représentent chacun de façon indépendante H, un hydrocarbyle ou un hydroxyhydrocarbyle ; ou R³ et R⁴ ensemble et/ou R⁵ et R⁶ ensemble et/ou R¹ et R³ ensemble et/ou R² et R⁴ ensemble peuvent former des groupes cycliques ; et x est un nombre de 1 à 8 ;
    (C-4) un composé renfermant du soufre représenté par la formule
    Figure imgb0093
     Formule I dans laquelle :
       R¹, R², R³ et R⁴ représentent chacun, de façon indépendante H ou des groupes hydrocarbyle ;
       R¹ et/ou R³ peuvent être G1 ou G2 ;
       R¹ et R² et/ou R³ et R⁴ peuvent être conjointement des groupes alcylène renfermant de 4 à 7 atomes de carbone ;
       G¹ et G² représentent chacun de façon indépendante C(X)R, COOR, C≡N, R⁵-C=NR⁶, CON(R)₂ ou NO₂, et G¹ peut être également CH₂OH, où X est O ou S, chacun des R et R⁵ représente, de façon indépendante, H ou un groupe hydrocarbyle, R⁶ est H ou un groupe hydrocarbyle ;
       lorsqu'à la fois G¹ et G² sont R⁵C=NR⁶, les deux groupes R⁶ peuvent représenter ensemble un groupe hydrocarbylène reliant les deux atomes d'azote ;
       lorsque G¹ est CH₂OH et G² est COOR, une lactone peut être formée par condensation intramoléculaire de G¹ et G² ; et
       x est un nombre entier de 1 à 8 ; et
    (C-5) un mélange de deux ou de plus de deux de l'un quelconque de (C-1) à (C-4).
  2. Une composition de la revendication 1, dans laquelle ledit composé acide organique comporte au moins un acide carboxylique aliphatique, cycloaliphatique ou aromatique.
  3. Une composition de la revendication 1, dans laquelle ledit composé acide organique comporte au moins un composé représenté par les formules :
    Figure imgb0094
     formules II et III dans lesquelles R est un groupe hydrocarbyle.
  4. Une composition de la revendication 1, dans laquelle ledit composé acide organique est représenté par la formule
    Figure imgb0095
     formule V dans laquelle, R⁷ et R⁸ sont des groupes hydrocarbyle aliphatiques, a et b sont des nombres dans la gamme de 0 à 5 sous la condition que la somme de a et b ne dépasse pas 5, et c est un nombre dans la gamme de 0 à 4.
  5. Une composition de la revendication 1, dans laquelle ledit composé acide organique comporte au moins un composé représenté par la formule



            Ra-Ar-(OH)b   (XII)



    formule XII dans laquelle, R est un groupe hydrocarbyle de 4 à 400 atomes de carbone, Ar et un groupe aromatique, a et b sont des nombres représentant chacun au moins 1, la somme de a et b se situant dans la gamme de 2 jusqu'au nombre d'hydrogènes déplaçables sur le noyau aromatique ou les noyaux aromatiques de Ar.
  6. Une composition selon l'une quelconque des revendications précédentes, dans laquelle le métal dans ledit sel (A) est choisi parmi le lithium, le sodium, le magnésium, le calcium, le potassium, le baryum, l'aluminium, le zinc, le cuivre ou un mélange de deux ou de plus de deux de ceux-ci.
  7. Une composition selon l'une quelconque des revendications précédentes, dans laquelle le composant (B) est choisi parmi le benzotriazole, le tolyltriazole ou un mélange de ceux-ci.
  8. Une composition selon la revendication 1, dans laquelle le composant (A) est au moins un composant choisi parmi le sulfonate de magnésium, le sulfonate de sodium, le salicylate de magnésium ou un mélange de deux ou de plus de deux de ceux-ci ;
       le composant (B) est au moins un composé choisi parmi le benzotriale, le tolyltriazole ou un mélange de ceux-ci ;
       le composant (C) est un mélange de
    (C-1) au moins un amide de l'acide phosphorodithioïque, et
    (C-2) au moins un ester de l'acide phosphorodithioique.
  9. Une composition selon la revendication 1, dans laquelle
       le composant (A) est au moins un sel métallique choisi parmi le phénate de calcium, le sulfonate de calcium, le sulfonate de magnésium, le sulfonate de sodium, le salicylate de magnésium, ou un mélange de deux ou de plus de deux de ceux-ci ;
       le composant (B) est au moins un composé choisi parmi le tolyltriazole, le benzotriazole ou un mélange de ceux-ci, et
       le composant (C) est au moins un composé choisi parmi
    (C-1) au moins un amide renfermant du phosphore dérivé de l'acide di(alkyl)phosphorodithioïque, de l'acrylamide ou du paraformaldéhyde ;
    (C-2) au moins un ester renfermant du phosphore dérivé de l'acide di(alkyl)phosphorodithioïque et de méthacrylate, post-traité avec de l'oxyde de propylène ;
    (C-3) au moins un parmi (i) un dithiocarbamate dérivé de la butylamine, du disulfure de carbone et de méthacrylate, (ii) au moins un dithiocarbamate couplé à du méthylène, dérivé de la diamylamine, du disulfure de carbone, de l'hydroxyde de sodium et du chlorure de méthylène, ou (iii) un mélange de (i) et (ii) ;
    (C-4) le 2,2'-dithiodiisobutyraldéhyde ; et
    (C-5) un mélange de deux ou de plus de deux de l'un quelconque de (C-1) à (C-4).
  10. Une composition selon la revendication 1 dans laquelle
       le composant (A) est du salicylate de magnésium ;
       le composant (B) est du tolyltriazole ; et
       le composant (C) est au moins un ester renfermant du phosphore dérivé de l'acide di(alkyl)phosphorodithioïque et de méthacrylate, post-traité avec de l'oxyde de propylène.
  11. Une composition selon la revendication 1, dans laquelle
       le composant (A) est du salicylate de magnésium ;
       le composant (B) est du tolyltriazole ; et
       le composant (C) est au moins un amide renfermant du phosphore dérivé de l'acide di(alkyl)phosphorodithioïque, de l'acrylamide et du paraformaldéhyde.
  12. Une composition selon l'une quelconque des revendications 1 à 11, comportant en outre au moins un composé choisi parmi un phosphite de dihydrocarbone, un phosphite de trihydrocarbone ou un mélange de deux ou de plus de deux de ceux-ci.
  13. Une composition selon la revendication 12, dans laquelle le diphosphite de dihydrocarbone est de l'hydrogéno-phosphite de dibutyle.
  14. Un concentré comportant de 10% à 90% en poids d'une composition selon l'une des revendications précédentes et un diluant.
  15. Un lubrifiant ou un fluide fonctionnel comportant une quantité prépondérante d'une huile et une quantité plus faible d'une composition selon l'une quelconque des revendications 1 à 13.
EP88910283A 1987-11-05 1988-10-21 Compositions et lubrifiants et fluides fonctionnels les contenant Expired - Lifetime EP0351428B1 (fr)

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AU657561B2 (en) * 1991-05-01 1995-03-16 Lubrizol Corporation, The Thermally stable compositions and lubricants and functional fluids containing the same
JP3086727B2 (ja) 1991-08-09 2000-09-11 オロナイトジャパン株式会社 低リンエンジン油製造用の添加剤組成物
US5356546A (en) * 1992-04-16 1994-10-18 The Lubrizol Corporation Metal salts useful as additives for fuels and lubricants
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CA2130139C (fr) * 1993-08-20 2004-06-29 Sean S. Bigelow Compositions lubrifiantes a stabilite thermique et a proprietes d'adherence ameliorees
DE69931758T2 (de) 1998-07-06 2007-06-06 The Lubrizol Corp., Wickliffe Gemischte phosphorverbindungen und diese enthaltende schmiermittel
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JP2003138285A (ja) * 2001-11-02 2003-05-14 Nippon Oil Corp 自動車用変速機油組成物
SG188788A1 (en) 2004-12-09 2013-04-30 Lubrizol Corp Process of preparation of an additive and its use
US8754017B2 (en) 2008-07-16 2014-06-17 The Lubrizol Corporation Lubricant for natural gas engines
US20150240181A1 (en) * 2014-02-26 2015-08-27 Infineum International Limited Lubricating oil composition
CN114437696B (zh) * 2021-12-31 2023-05-30 华东理工大学 一种粘弹性表面活性剂组合物及其制备方法与应用

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US4466894A (en) * 1983-04-20 1984-08-21 The Lubrizol Corporation Phosphorus-containing metal salts/sulfurized phenate compositions/aromatic substituted triazoles, concentrates, and functional fluids containing same
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EP0351428A1 (fr) 1990-01-24
WO1989004358A3 (fr) 1989-08-24
CA1337413C (fr) 1995-10-24

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