Classifications

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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
  • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
  • C10M135/10—Sulfonic acids or derivatives thereof
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  • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
  • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
  • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
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  • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
  • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
  • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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  • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
  • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
  • C10M133/38—Heterocyclic nitrogen compounds
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  • 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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  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
  • C10M2209/062—Vinyl esters of saturated carboxylic or carbonic acids, e.g. vinyl acetate
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
  • C10M2215/226—Morpholines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
  • C10M2215/26—Amines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
  • C10M2215/30—Heterocyclic compounds
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/044—Polyamides
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/045—Polyureas; Polyurethanes
• • C—CHEMISTRY; METALLURGY
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/046—Overbased sulfonic acid salts
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
  • C10N2060/04—Oxidation, e.g. ozonisation

Definitions

• the present invention relates to ashless corrosion inhibiting compositions with excellent demulsibililty characteristics which include amine salts of dinonylnaphthalene sulfonates, alone or in combination with synergists.
• Lubricating oils and the like are commonly modified through the use of various additives or improvement agents for use in internal combustion engines, such as automotive, light aircraft and diesel engines.
• these lubricating oils require the use of additive agents to render them serviceable under the adverse environmental conditions frequently encountered in the operation of these engines.
• oil-soluble metal sulfonates give enhanced corrosion protection, particularly in salt-containing environments, when combined with weak acids, such as carboxylic acids, and their ester and soap derivatives. Although not well understood, it is generally believed that this synergism involves mixed surface monolayers, analogous to mixed micelles. These oil-soluble metal sulfonates are useful as additives in fuels and in lubricating oil additives for engines.
• the metal sulfonates retard the accumulation of sludge and thereby prevent engine fouling by virtue of their dispersant activity. They also function as corrosion inhibitors. However, since they contain metals, these conventional additives form ash deposits (i.e., solid residues) after combustion in the engine when added to the lubricating oil. Therefore, it is desirable to provide other additives which have similar desirable qualities without the presence of the ash-forming metal.
• Dinonylnaphthalene sulfonic acid (HDNNS®, available commercially from King Industries, Inc. Norwalk, CT, U.S.A.) is well-known in the art as a replacement for petroleum sulfonic acids which are used in rubber plasticizers and processing aids, and the metal salts of this acid also have proven to be excellent for use in oil-soluble corrosion inhibitors.
• dinonylnaphthalene sulfonic acid and its salts form inverted micelles in non-polar media with the polar ends of the molecules turning inward.
• the extreme tendency of dinonyl­naphthalene sulfonic acid salts to form miceller aggregates is consistent with a strong tendency to form monolayers at oil/air and oil/metal interfaces.
• the formation of very stable monolayers at oil/metal interfaces helps to explain why metal salts of dinonyl­naphthalene sulfonic acid, particularly the barium, calcium and zinc salts, are effective oil-soluble corrosion inhibitors.
• amine sulfonates have been used as promoters in overbasing calcium or magnesium sulfonates.
• over-based means that the sulfonates contain an amount of magnesium substantially in excess of that required to form a neutral sulfonate.
• Sabol et al. in U.S. 4,201,682 over-based oil-soluble magnesium sulfonate compositions by one-step carbonation of a reaction mixture containing magnesium hydroxide.
• the sulfonate anion-affording materials used for the formation of the neutral magnesium sulfonate in the over-based product are oil-soluble sulfonic acids such as alkyl-substituted benzene or alkyl-naphthalene sulfonic acids.
• oil-soluble sulfonic acids such as alkyl-substituted benzene or alkyl-naphthalene sulfonic acids.
• Arnold et al. in U.S. 4,225,446 disclose an improved process for the preparation of fluid, highly basic magnesium sulfonates useful as lubricants for engines and as diesel fuel additives. the Arnold et al. process uses oil-soluble sulfonic acids prepared from alkyl or alkaryl hydrocarbons.
• Vaughan in U.S. 4,248,718 discloses overbased dispersants for lubricating oils having a very low ash content in comparison to the conventional overbased additives. These are prepared by reacting an ashless nitrogen-containing compound such as ammonia with a basically reacting metal compound, a suspending agent, a chalcogen compound such as carbon dioxide, and preferably a promoter such as ethanol.
• amine sulfonates as promoters in overbasing metal sulfonates, they have also been used as dispersants.
• U.S. 3,960,937 discloses ashless additives for lubricating oils obtained by first reacting a petroleum sulfonic acid and a polyamine and then combining the product with a cyclic anhydride of a dicarboxylic acid.
• compositions avoid the presence of an ash forming metal, they do not form deposits when used as detergent additives for lubricating oils such as engine oil or when added to oil which is mixed with gasoline in 2-stroke engines.
• U.S. 3,979, 478 discloses that when amino resins such as urea formaldehyde and melamine formaldehyde thermosetting resins are cured with high molecular weight polyalkylaromatic sulfonic acids, curing occurs much more rapidly at conventional temperatures than achieved previously.
• amine dinonylnaphthalene sulfonates are very effective ashless corrosion inhibitors by themselves and show strong synergism when combined with carboxylic acid derivatives. Moreover, when careful attention is paid to the type of amine used surprising and unexpected enhancement of demulsibility is obtained.
• the particular amine dinonylnaphthalene sulfonates of this invention may be used in many corrosion inhibiting applications where metal sulfonates cannot be used and where ashless additives are nearly essential, such as in gasoline, fuel oil, and 2-cycle engine oil, while limiting any tendency to form stable emulsions which is bad.
• the present invention further contemplates such corrosion inhibiting compositions which further comprise a synergist such as a petroleum oxidate, an oil-soluble carboxylic acid, a metal or amine soap thereof, an ester thereof, an amide thereof, or a mixture of any of the foregoing.
• a synergist such as a petroleum oxidate, an oil-soluble carboxylic acid, a metal or amine soap thereof, an ester thereof, an amide thereof, or a mixture of any of the foregoing.
• the alkylaromatic sulfonic acid is dinonylnaphthalene sulfonic acid, the nonyl radicals of which are highly branched.
• the amine component (ii) comprise an aliphatic monoamine, an aliphatic polyamine, or a substituted or unsubstituted aliphatic heterocyclic amine.
• articles comprising a metallic substrate normally susceptible to corrosion and, on at least a portion of the substrate, a protective layer of an ashless corrosion inhibiting composition defined above.
• the alkylaromatic sulfonic acid comprising component (i) can vary widely in chemical nature, so long as it has a minimum molecular weight of about 350. If a phenyl nucleus is present, these requirements can be met with a benzenesulfonic acid containing at least about one or two alkyl groups having a total of at least about 14 carbon atoms, e.g., didocecylbenzenesulfonic acid.
• the aromatic nucleus can be polycyclic, e.g., naphthyl, anthracyl, phenanthryl, etc. Many variations in the position of substitution are possible and contemplated and mixed positional isomers are included.
• the alkyl substituents can be straight or branched chain. Best results are obtained with maximum variations in substituent locations and with maximum branching.
• alkylaromatic sulfonic acids are branched alkyl-substituted naphthalenesulfonic acids. These are available, for example, by sulfonating polyalkylnaphthalenes.
• the polyalkylnaphthalenes can be made by alkylating naphthalene with olefins, for example, propylene trimer or tetramer, or alkyl halides, with a suitable catalyst, e.g., hydrogen fluoride or anhydrous aluminum chloride in a suitable solvent such as naphtha, sulfur dioxide, nitrobenzene or a mixture of benzene and nitrobenzene. See Robert G. King and George W.
• dinonyl­naphthalene is dissolved in an inert solvent, such as petroleum naphtha, hexane, heptane, octane, chlorinated solvents, and the like, and sulfuric acid, preferably oleum, is introduced into the solution at the desired temperature and with agitation.
• sulfuric acid preferably oleum
• the sulfonic acid is recovered by separating and drawing off a heavy spent sulfonic acid layer and then extracting the sulfonic acid water to remove poly­sulfonic acids and residual sulfonic acid.
• the nitrogen-containing compound corresponding to component (ii) serves as a source of supply of basic material in the additives of this invention.
• ashless is meant a substance which after combustion has no non-volatile residue.
• This ashless nitrogen-­containing compound can vary broadly. It will be an amine containing at least 3 carbon atoms and no oxygen atoms. Mixtures of different amines may also be used. In general, the amines will be selected from readily available aliphatic amines, polyamines, substituted and unsubstituted aliphatic heterocyclic amines, and the like.
• Amines preferred for use in this reaction are aliphatic monoamines and polyamines having from at least 3 up to 50 carbon atoms in the aliphatic portion of the molecule, and aliphatic polyamines such as propanedi­amine and the like.
• Aliphatic monoamines include propylamine, octylamine, dicosoamine, decylamine, di(octyl)amine, tallowamine, eicosylamine, and the like.
• the amine may be derived from natural or synthetic sources using methods well known in the art.
• Preferred monoamines are C3 ⁇ 20 alkylamines and particularly preferred are the C3 ⁇ C8 alkylmonoamines.
• the polyalkylenepolyamines are prepared for example from ammonia and ethylenechloride or ethylene oxide and have a general repeating structure H2N(CH2CH2) x H where x is 2-20. Especially preferred compounds are those where x is 2-6.
• the aliphatic heterocyclic amines are those well known amines including substituted and unsubstituted piperidines, pyrrolidines and the like.
• the ethyleneamines are those well known amines such as diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine and the like.
• Propyleneamines are a class of polyamines prepared by the reaction of acrylonitrile with an ethyleneamine, such as those described above and having the formula H2N(CH2CH2) x H where x is 1 to 5, followed by hydrogenation of the resultant intermediate.
• the products prepared from ethylenediamine and acrylonitrile would be H2N(CH2)3NH(CH2)2NH(CH2)3NH2.
• the most preferred amines are diethylene triamine, triethylenetetramine, 2-methylpentanediamine, and 3-methylpiperidine.
• diluents both volatile and non-volatile, are suitable for use in the compositions of the present invention.
• the principle requisites desired in a diluent are that it acts as a solvent for the various components. If an oil, it should have a flash point of 385°-400°F. or above.
• oils both natural and synthetic such as naphthenic bases, paraffin bases diesters and mixed-base oils may be used.
• the diluent oil is a naphthenic lubricating oil.
• this naphthenic lubricating oil has a viscosity range of 50-200 SUS at 100°F.
• Natural and synthetic solvents well known in this art such as poly-alpha-olefins, mineral spirits, kerosene, polyglycols, and the like, can also be used as the diluents.
• synergists can comprise any of the carboxylic acids or derivatives and/or petroleum oxidates conventionally used as synergists with prior art metal sulfonates.
• the synergist comprises oxidized petrolatum.
• compositions according to the present invention are to be used as corrosion-­inhibiting coatings for metals, it is possible to add suitable thickeners in effective amounts.
• the thickeners which can be used may be any of the well known thickeners of the prior art.
• the thickener if used, will comprise an oxidized polyethylene wax, a polyamide thixotrope, an overbased calcium sulfonate, an ethylene-vinyl acetate copolymer, and the like in an amount of, for example 0.01 to 5 percent by weight of the total composition.
• the amine salts of the polyalkylaromatic polysulfonates may be prepared by any of the methods well known in the art. One such method of their preparation is set forth in previously-mentioned U.S. Patent No. 2,764,548.
• the corrosion-inhibiting compositions in accordance with the present invention may be prepared by providing an effective amount of the dinonylnaphthalene amine sulfonate in the diluent.
• a concentrate can first be prepared and this may be further diluted with the same or another diluent or mixutre of such diluents.
• the relative amounts of the amine sulfonates may be varied widely. Generally, they are provided in similar proportions to the proportions of metal sulfonates used in the prior art. It is preferred, however, that a 50 percent active salt (in diluent oil) be diluted to from about 20 to 70 percent by weight with the diluent for use.
• the synergist may be added to the composition in proportions well known in the art as applied to the metal sulfonates. It is preferred, however, that the synergist and sulfonate be present in the composition at a combined amount from about 10 to about 99 percent by weight of the total composition.
• Amine dinonylnaphthalene sulfonates in accordance with the present invention and of the prior art were prepared by direct neutralization of 38 percent active dinonylnaphthalene sulfonic acid in heptane with the appropriate amine, oil addition, and stripping with final adjustment to 50 percent active sulfonate content.
• the diluent oil used was a 75 second solvent-extracted naphthenic oil (Telura® 415, commercially available from Exxon Corp.).
• the particular amine dinonylnaphthalene sulfonates prepared are shown in Table 1.
• the first four amine dinonylnaphthalene sulfonates listed in Table 1 are based on the series H2N-(CH2CH2NH) n -H, where "n" varies from 0 to 3. Barium dinonylnaphthalene sulfonate was also prepared as a control sample corresponding to the prior art.
• AMINE SULFONATE SUMMARY All sulfonates are 50% active in naphthenic oil Designation Description
• AMM-S 50% Ammonium dinonylnaphthalene sulfonate (DNNS)
• DNNS Ammonium dinonylnaphthalene sulfonate
• EDA-S 50% Ethylene diamine DNNS
• DETA-S 50% Diethylene triamine DNNS
• TETA-S 50%
• Triethylene tetramine DNNS 2-MPD-S 50% 2-Methylpentane diamine DNNS 3-MP-S 50% 3-Methylpiperidine DNNS Comparison: BA-S 50% Barium DNNS
• the six amine sulfonate preparations were each diluted to 10% and 15% by weight in 75 second viscosity naphthenic oil.
• a third mixture was also made up consisting of 7.5% of the particular amine sulfonate preparation and 7.5% oxidized petrolatum with an acid value of 55 (ALOX® 600, ALOX Corporation), to evaluate possible synergistic behavior.
• equivalent mixtures were made using a 50% active barium dinonylnaphthalene sulfonate in oil (NA-SUL®BSN King Industries).
• the film thickness (in mils), was determined by weighing before and after film removal after 24 hours vertical draining, not including the lower edge where an extra "bead" is normally left.
• Examples 26-29 are directed to the effects of film thickness in oil-based systems.
• a 2-MPD-S/oxidate system (7.5% of each) is provided as the constant active component.
• Four thickeners were used: an oxidized polyethylene wax (Polymekon 300, Bareco); a polyamide thixotrope used in conventional hard coatings (DISLON® 6500, King Industries, Inc.); an overbased calcium sulfonate (SACI 200A, Witco); and an ethylene-vinyl acetate copolymer (AC-400, Allied).
• Examples 38-43 show the demulsibility of amine sulfonates in oil, as compared to reference Example 44-46.
• a demulsifier is a surface-active material which de-stabilizes emulsions.
• water-in-oil emulsions can form readily as a result of water contamination, and "demulsibility", the tendency for such emulsions to break in the absence of shear, is an important characteristic.
• One of the more widely used demulsibility tests is ASTM D-1401 (American Society of Testing Materials), in which 40 ml each of water and oil are mixed in a grauated cylinder and then allowed to separate. The cylinders are observed at 5 minute intervals, and the time required to reach 3 ml or less of emulsion layer is taken as a measure of the demulsibility.
• Demulsibility results obtained with three 50% active barium and calcium sulfonates are shown for comparison.
• an ammonium or EDA sulfonate both of which are outside the present invention exhibit slow separation at very low concentrations, rapid separation at intermediate concentrations and very slow separation at high concentrations (Comparative Example 38 and 39).
• a normal divalent metal dinonylnaphthalene sulfonate shows moderate separation time at low levels, which improves and levels off with increasing concentrations.
• Monovalent metal dinonylnaphthalene sulfonates generally separate more slowly with increasing concentration, and alkyl benzene sulfonates behave similarly.
• didodecylnaph­thalene disulfonic acid and the like may be used as the polyalkylaromatic polysulfonic acid instead of dinonyl­naphthalene disulfonic acid. All such obvious variations are within the full intended scope of the appended claims.

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• 1989
  • 1989-02-22 DE DE8989200438T patent/DE68901672T2/de not_active Expired - Lifetime
  • 1989-02-22 EP EP89200438A patent/EP0335429B1/de not_active Expired - Lifetime
  • 1989-02-22 AT AT89200438T patent/ATE76894T1/de active
  • 1989-03-21 CA CA000594341A patent/CA1338549C/en not_active Expired - Fee Related
  • 1989-03-22 JP JP1070286A patent/JP2729396B2/ja not_active Expired - Fee Related

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