Classifications

• • C—CHEMISTRY; METALLURGY
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
  • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
  • C10M133/56—Amides; Imides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
  • C08C19/00—Chemical modification of rubber
  • C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
  • C08C19/34—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with oxygen or oxygen-containing groups
  • C08C19/36—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with oxygen or oxygen-containing groups with carboxy radicals
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  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
  • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
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  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
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  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/26—Overbased carboxylic acid salts
  • C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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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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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
  • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
• • 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
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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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
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/045—Metal containing thio derivatives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
  • C10M2229/04—Siloxanes with specific structure
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
  • C10M2229/04—Siloxanes with specific structure
  • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
  • C10M2229/04—Siloxanes with specific structure
  • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
• • C—CHEMISTRY; METALLURGY
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
  • C10M2229/04—Siloxanes with specific structure
  • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/04—Groups 2 or 12
• • C—CHEMISTRY; METALLURGY
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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/02—Bearings
• • C—CHEMISTRY; METALLURGY
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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• lubricants which meet a F viscosity specification and a 2l0F viscosity specification. such as is shown for motor oils by the following table derived from SAE. 1300a taken from the SAE Handbook for I969:
• an SAE l0W/50 oil must have a viscosity at 0F between 12 and 24 poises and a viscosity at 2 l0F of between 85 and l SUS.
• VI viscosity index
• pour point depressants A common limitation of essentially all of these is shear sensitivity. This is not unexpected. since most of these polymers are relatively high molecular weight materials. and consequently are readily subject to shear degradation. On the other hand. relatively low molecular weight polymeric materials, at least up to the present time. have proven to be relatively ineffective as thickeners or VI improvers in automotive engine lubricants, even though they may have reasonably good shear stability.
• a number of polymeric additives having a certain polarity have been suggested as lubricating oil additives. These include. for example, polymers shown as sludge dispersants in-U.S. Pat. No. 2.838.456. In this patent. reference is made to graft copolymers wherein a polar monomer is grafted onto a polymer of an isoolefin or a diene. Not only is the polymer left in a nonhydrogenated state (and therefore susceptible to oxidation) but also the proportion of the polar monomer em ployed was so high as to seriously reduce oil solubility of the graft copolymer.
• lubrieating compositions comprising a major proportion of a lubricating oil and 0.1-109? by weight of the halogen-free nitrogen-containing amido amine reaction product of a terminally carhoxylated substantially completely hydrogenated polyisoprenc having an average molecular weight between about 20,000 and 250,000 and a nitrogen compound ofthe group consisting of polyalkylene amines (sometimes referred to as polyalkylene imines) and hydroxyl polyalkylene amines.
• amido amine reaction products to be described more fully hereinafter, not only increase the viscosity of hydrocarbon oils but also increase the viscosity index thereof and provide detergency and dispersancy properties. Furthermore, these reaction products are stable with respect to oxidation and shear.
• the percursors of the polymeric additives are preferably formed by polymerization of isoprene using a lithium-base initiator, preferably a lithium alkyl in an inert solvent medium predominating in hydrocarbons under conditions known in the art to produce a polyisoprene referred to as a living polymer wherein the growing end of the polymer chain is associated with a lithium radical.
• This living polymer is then subjected to carboxylation such as by reaction with carbon dioxide to form a polyisoprene bearing a terminal carboxyl group.
• the carboxylated polymer is then subjected to hydrogenation under conditions leading to substantially complete reduction of all aliphatic unsaturation.
• substantially complete means hydrogenation to an extent sufficient to reduce at least about 9871 of the olefinic unsaturation and preferably higher than about 99% thereof.
• Hydrogenation is preferably effected by the use of catalysts which are the reaction products of a nickel or cobalt carboxylate and a halogen-free organo alkenc compound. preferably an aluminum trialkyl.
• the temperature of hydrogenation may vary from about room temperature to about 175C for times from about 1 minutes to 4 hours. Hydrogenation is normally conducted in a saturated hydrocarbon medium and may be carried out in a batch operation in an autoclave or in a continuous process utilizing trickle phase techniques. for example.
• the average molecular weight of the polyisoprene component may vary over a wide range. It is preferred that it lie between about 21,500 and 250.000, still more preferably between about 23,000 and 80.000.
• the nitrogen compounds utilized for the formation of the amido amines of this invention may be polyalkylene amines, and hydroxy alkyl polyalkylene amines as well as mixtures thereof.
• polyalkylene amine is meant to include those polyamines having the formula:
• R is a hydrogen or a lower alkyl hydrocarbon substituent and alkylene" is a lower alkylene, i.e. divalent open chain hydrocarbon group having from 1 to 8 carbon atoms.
• alkyl polyalkylene amines are those in which the terminal hydrogen atom in the above structural formula is replaced by a hydroxy alkyl radical or a polyalkylene oxide, hydroxy terminated radical in which the alkyl group has from 1 to 8 carbon atoms.
• Typical species of reactants falling within the above-described group of compounds are the following:
• the amido amine reaction products are directly prepared by reaction of the earboxylated hydrogenated polyisoprene and one or more of the above-described nitrogen-containing compounds. While little or no reaction occurs at relatively lower temperatures such as 145C. it has been found that satisfactory rates of reaction are experienced at temperatures in the order of lC or higher, preferably 185-250 in the presence of a lubricating oil if desired or in bulk form. By this means when using a lubricating oil medium for the reaction. a concentrate of the amido amine can be conveniently prepared.
• Heating is continued for periods of time which will vary with the reactants and temperature but it normally will be between about 15 minutes and 8 hours. If the product is prepared in the absence of a lubricating oil it may be recovered for example by dissolving in toluene, washing with a lower alcohol such a methanol and precipitating the product between addition of still further alcohol.
• the reaction products prepared as described above comprise a hydrogenated polyisoprene segment connected by a single amido linkage with the polyamine. It is preferred as referred to hereinabove that the hydrogenated polyioprene segment have an average molecular weight between about 23,000 and 80,000 and in conjunction therewith that the nitrogen compound utilized to form the amido amine have an average molecular weight between about 150 and 1800 although polyalkylene amines having average molecular weights up to about 2,500 may in fact be used.
• the oil component of the lubricating compositions according to the present invention is especially designed for the preparation of multi-grade lubricants although single grade lubricants may be compounded as well. Still more specifically, the present combination of block copolymer and pour point depressant is especially beneficial in wax-containing lubricating oil cuts such as found in Mid Continent oils, West Texas Ellenburger crudes, East Texas crudes, Oklahoma crudes, Pennsylvania crudes and California crudes and similar waxy crudes which may be referred to as paraffin base crudes, naphthenic crudes or mixed based crudes as distinguished from asphalt base crudes. While lubricating oils of any viscosity may be used as the base for the present compositions.
• High Viscosity lndex Neutrals such as HVl 100 Neutral, HVI 250 Neutral and HVI Bright Stock as well as combinations of the same.
• the numerals before Neutral are approximate viscosities at 100F in Saybolt Universal Seconds.
• very high viscosity index (VHVI) oils such as those prepared via hydrocracking of poor quality oils, such as low viscosity index (LVI) oils
• LVI low viscosity index
• More volatile oils may be employed for special purposes such as (HVI) N.
• These neutral oils are produced by well-known refining meth ods, such as distillation. dewaxing, deasphalting, dearomatizing as by solvent extraction, etc, as may be needed. dependent largely on the crude oil used. Typical properties of these HVI oils are the following;
• EXAMPLE I EXAMPLE III Polyisoprene was prepared in isopentane solution using secondary butyllithium as the initiator to produce a polymer having an average molecular weight of about 30.000.
• the living polymer was carboxylated at about 40C by the use of carbon dioxide. This was subjected to hydrogenation in the presence of a catalyst comprising the reaction product of nickel octoate and aluminum triethyl to form the hydrogenated carboxylated polymer.
• the product was dissolved in xylene and reaction at 145C was attempted with pentaethylene hexamine (PEHA). Little or no reaction occurred at this temperature. However. when the temperature was increased to 200C reaction occurred to form a homogenous mixture after several hours.
• the cooled polymer was dissolved in an excess of toluene and washed with methanol which caused the product to precipitate free of unreaetcd polyamine.
• the polymer was dissolved in toluene dried with sodium sulfate and the solvent stripped off.
• the product characterized by the infra red spectra and physical properties was shown to be the same as the amido amines obtained by way of the intermediate acid chloride reactant referred to hercinabove.
• EXAMPLE II In order to determine the dispersant properties of the two amido amines prepared as described in Example I. the additives were dispersed in a base blend and subjected to Micro Air Oxidation Tests (MAOT). The
• This lubricating oil had an SAE grade of iOW/40.
• the Dispersant VI lmprover of this Invention present in an amount of 2.0 wt.% was the amido amine of hydrogenated carboxylatcd polyisoprene and polyethylene iminc. the respective average molecular weights of each were 48.000 and 600. The following ratings were obtained and are compared with specification limits.
• a lubricating composition comprising a major proportion of a lubricating oil and 0. l-l by weight. sufficient to raise the viscosity index and impart deter- ,gcncy to the oil of a halogen-free nitrogen-containing amido amine reaction product of a terminally carboxylated substantially completely hydrogenated polyisoprenc containing less than 27: of the original olefinic unsaturation and having an average molecular weight between about 20.000 and 250000 and a nitrogen compound of the group consisting of polyalkylene amines and hydroxy alkyl polyalkylene amines, said reaction product resulting from heating the hydrogenated carboxylated polyisoprenc and nitrogen compound for l480 minutes at l75250C.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Lubricants (AREA)

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Cited By (21)

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Citations (5)

• 1974
  • 1974-03-06 US US448603A patent/US3903003A/en not_active Expired - Lifetime
• 1975
  • 1975-03-04 JP JP50025723A patent/JPS50122505A/ja active Pending
  • 1975-03-04 FR FR7506719A patent/FR2263253B1/fr not_active Expired
  • 1975-03-04 DE DE19752509374 patent/DE2509374A1/de active Pending
  • 1975-03-04 GB GB8896/75A patent/GB1505143A/en not_active Expired
  • 1975-03-04 NL NL7502510A patent/NL7502510A/xx unknown

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