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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
  • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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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
  • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/287—Partial esters
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/287—Partial esters
  • C10M2207/288—Partial esters containing free carboxyl groups
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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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
  • C10M2207/40—Fatty vegetable or animal oils
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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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/40—Fatty vegetable or animal oils
  • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/064—Di- and triaryl amines
  • C10M2215/065—Phenyl-Naphthyl amines
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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
• • C—CHEMISTRY; METALLURGY
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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
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
• • 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
  • 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
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/30—Heterocyclic compounds
• • 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
  • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
  • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
• • C—CHEMISTRY; METALLURGY
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  • 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
  • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
  • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/135—Steam engines or turbines
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/20—Metal working
  • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
• • 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
  • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
  • C10N2050/10—Semi-solids; greasy

Definitions

• hydroabietyl alcohol is composed of 13-15 per cent of a non-alcohol fraction and the balance is about 15 per cent dehydroabietyl alcohol, 40 per cent dihydroabietyl alcohol and 45 per cent tetrahydroabietyl alcohol. It will be understood that the distribution of the alcohols averages that given hereinbefore but will vary from batch to batch.
• hydroabietyl alcohol is typical of a primary monohydric alcohol plus what might be expected from the residual unsaturation in the ring structure. Nevertheless, it has been found that as an additive to mineral oil to produce a compounded mineral oil for use as a gear lubricant or a cutting oil or a turbine oil, the similarity between esters of hydroabietyl alcohol and esters of a primary monohydric aliphatic alcohol ceases to exist. It is true that hydroabietylalcohol reacts with monoand dicarboxylic acids to produce esters but the similarity between hydroabietyl alcohol and oleyl alcohol, for example, ceases at that point.
• esters of hydroabietyl alcohol may give the 5 improved results to be discussed hereinafter because of the structure of the alcohol, because of the degree of unsaturation of the major portion of the alcohol fraction or for other reasons at present unknown.
• the three alcohols present in hydroabietyl alcohol have the following structures:
• esters prepared from the commercial hydroabietyl alcohol and hydroxy aliphatic polycarboxylic acids are useful as rust inhibitors in turbine oils and as extreme pressure additives in lubricants such as gear oils.
• Typical esters are di-hydroabietyl malate, dihydroabietyl tartrate, tri-hydroabietyl citrate, hydroabietyl-2-ethylhexyl malate, hydroabietyl- 2-ethylhexyl tartrate, di-hydroabietyl-2-ethylhexyl citrate, hydroabietyl-di-2-ethylhexyl citrate, hydroabietyl-oleyl malate, hydroabietyloleyl tartrate, di-hydroabietyl-oleyl citrate, hydroabietyl dioleyl citrate, and similar esters of hydroxy aliphatic polycarboxylic acids in which all of the carboxyl groups are esterified with hydroab
• the solvent was then removed by gradually reducing the pressure in the reactor.
• the solvent-free product was warmed to 130 C., and filtered to remove abietyl alcohol and the other carboxyl group is 5 solids.
• the filtered product had a neutralization esterified with a monohydric aliphatic saturated number of 13.3 indicative of neutral ester content or unsaturated straight chain or branched chain of about 89 per cent.
• Hydroabietyl-Z-ethylhexy1 malate was precarboxyl groups of a tricarboxylic acid are esteripared in a manner similar to that employed in fied with hydroabietyl alcohol and the others 10 preparing di-hydroabietyl malate by reacting 0.5 esterifled by a monohydric saturated or unsatumole of hydroabietyl alcohol, 0.5 mole Z-ethylrated straight or branched chain monohydric hexanol and 0.5 mole dl-inalic acid.
• hydroabietyl alcohol dicative of a neutral ester content of about 88.6 is used herein to designate the mixture of alcoper cent. hols, esters and hydrocarbons discussed herein- Hydroabietyl oleyl malate was prepared from before. 0.375 mole of hydroabietyl alcohol, 0.375 mole of In determining the amount of hydroabietyl aloleyl alcohol and 0.375 mole of dl-malic acid.
• the cohol to be reacted with a predetermined amount filtered product had a neutralization number of of polycarboxylic acid, it is necessary to bear in 16.0 indicative of a neutral ester content of about mind that the presently available commercial hy- 88 per cent. droabietyl alcohol is, as pointed out hereinbefore, Each of the foregoing products was subjected a mixture of alcohols, esters and hydrocarbons. to the A. S. T. M. Test D665-44T.
• the amount of the mixture ema cylindrical polished steel specimen is suspended ployed will be dependent upon the hydroxyl numand soaked in 300 milliliters of the test oil at her of the available commercial hydroabietyl al- 140 F., for minutes. Thirty milliliters of discohol. One gram molecular weight of hydrotilled water are added then and the mixture is abietyl alcohol contains 17 grams of the hydroxyl stirred at 1000 R. P. M. After 48 hours the steel group. A determination of the hydroxyl number specimen is removed and examined for evidence of the commercial hydroabietyl alcohol used in 30 of rust.
• the base oil of a cutting oil may be a sulfurized mineral oil, a sulfurized and a chlorinated oil combined with mineral oil of suitable viscosity and additives included for various purposes.
• a cutting oil may have the following compositions.
• Sulfurized-chlorinated fatty oil contg about 5% sulfur and about 5%chlorine; per cent... 0. 25-15 0. 5-4. 0 Mineral oil. 50-500 100 F., SUV; per cent. 78-99 95-99. 0 Stain Inhibitor; per cent 0-2 0.1-0. 5 Hydroabietyl ester of alpha-hydroxy aliphatic polycarboxylic acid; per cent 0.1-5 0. 25-0. 6
• Blends within the ranges set forth hereinbefore were made and subjected to several tests to determine the effectiveness of the novel hydroabietyl esters in comparison with prior art additives which have proved efiective.
• the blends were subjected toa tapping test, the Oster threading test and a drill life test.
• Tapping test In the measurement of tapping emciency of an oil, a series of holes are very accurately drilled in a test metal, namely SAE-1020 steel. These holes are subsequently tapped with a series of taps, in a drill press equipped with a table, which is free to rotate about the center, being mounted on ball bearings. A torque arm is attached to this "floating table and this arm in turn actuates a spring scale so that the actual torque during tapping with the oil being evaluated is measured directly.
• the same taps used in evaluating the test oil are employed in tapping with a standard reference oil, which has arbitrarily been assigned an efiiciency of 100 per cent. The average torque for the test oil is compared to that of the standard and a relative efficiency is calculated on a percentage basis. For example:
• the drill life test is determined by using ten' drills ground to specified angles, three of which are placed in the chucks of a triple spindle head of the drill press. Holes are then drilled through flats of SAE 3140 steel until drill failure occurs. This is evidenced by excessive noise, tool burning and deterioration at the cutting edges. The failed drill is replaced with .a newly ground one and the test is continued until all ten drills fail.
• the drill life is the average of the number of holes obtained per drill before failure.
• Additive HO comprised the hydroabietyl oleyl malate prepared as described hereinbefore.
• Additive HOC comprised the hydroabietyl octyl (2-ethylhexyl) malate prepared as described hereinbefore.
• Additive DIH comprised the di-hydroabietyl malate prepared as described hereinbefore.
• Additive DAM comprised the neutral malate ester of an uiisaltulrated high molecular weight aliphatic monohydric a co 0
• Additive MAM comprised a compound ester in which both carboxyl groups of malic acid are esterified by a monoglycol ester of a high molecular weight aliphatic monocarboxylic acid.
• Ester H0 has the following structure:
• R is a high molecular weight olefinic radical and R" is the radical from the hydroabietyl alcohol mixture.
• the novel ester is about twice as efilcient as the prior art ester-type additive.
• esters having both carboxyl groups of an hydroxy aliphatic polycarboxylic acid esterified with radicals from hydroabietyl alcohol mixture are all more effective than. similar esters of aliphatic alcohols, there is an advantage to the use of either mixed esters or mixtures of esters. This advantage results from the viscosity of the various esters. As is manifest after a consideration of the following tabulation of viscosities of. various esters, di-hydroabietyl malate, for example, is far more viscous than the mixed esters.
• the high viscosity of the di-hydroabietyl esters makes it desirable to reduce the viscosity without sacrificing a disproportionate amount of the effectiveness of the hydroabietyl esters. As will be appreciated by study of the following tabulation this can be done by using mixed esters.
• Fluidity of the product can be obtained by employing mixed esters of alpha-hydroxy polycarboxylic aliphatic acids in which from 50 mole per cent to 100 mole per cent hydroabietyl radical and from 1 to 50 mole per cent of an alkyl radical are present in the carbalkoxy groups (carbalkoxy being inclusive of carbcycloalkoxy).
• the alkyl groups are those derived from monohydric aliphatic saturated or unsaturated alcohols having'from one through 18 carbon atoms and includes oleyl alcohol.
• a mechanical mixture is made of anhydroabietyl ester of an alpha-hydroxy aliphatic polycarboxylic acid and an ester of an alphahydroxy aliphatic polycarboxylic acid and a. monohydric aliphatic alcohol having 8 to 20 carbon atoms in the proportion to produce the desired viscosity and the mixture added to the oil to be fortified.
• the amount of hydroabietyl alcohol employed is based upon the hydroxyl number of the available mixture containing the hydroabietyl alcohol. That is to say, one mole of alcohol is equivalent to 17 grams of hydroxyl radical.
• esters are satisfactory for use in cutting oils it is preferred to use esters which are a mixture of neutral and partial esters for anti-rust agents. Therefore, it is preferred to use esters having a neutralization number of zero to 30 in cutting oils but esters having a minimum neutralization number of 10 in anti-rust oils, such as turbine oils.
• the present invention contemplates the addition of the novel esters to simple or compound mineral oils of lubricating grade in the proportion of about to about 99 per cent by weight of base oil to about 10 to l per cent, preferably 0.1 to 2 per cent by weight of the novel ester.
• the present invention provides a novel composition of matter comprising a major proportion of a base oil and a minor proportion of the novel esters effective to inhibit rusting and to enhance the extreme pressure properties of the base oil.
• the base oil is a lubricating fraction of mineral oil, a conventional gear lubricant base, a cutting oil or a grease.
• a novel composition of matter comprising moderately sulphurized mineral oil containing about 0.9% ctive sulphur, 0-99 weight percent; chlorinated base containing about 42% chlorine, 0-15 weight percent; mineral oil 50-500" 100 F. SUV, 0-99 weight percent, and about 0.1 to 10 weight percent of an ester product of malic acid in which about 50-100 mole percent of the radicals attached to the carbonyl carbon atoms through oxygen is radicals of hydroabietyl alcoho-l and the balance is a radical of a monohydric' aliphatic alcohol having 8-20 carbon atoms.
• a novel composition of matter comprising sulphurized and chlorinated fatty oil containing about 5% sulphur and about 5% chlorine, 0.25 to about 15 weight percent; mineral oil, 50-500" 100 F. SUV, about '78 to about 99 weight percent; stain inhibitor, 0.1 to 10 weight percent of an ester product of malic acid in which about 50-100 mole percent of the radicals attached to the carbonyl carbon atoms through oxygen is radicals of hydroabietyl alcohol and the balance is a radical of a monohydric aliphatic alcohol having 8-20 carbon atoms.
• a novel composition of matter consisting essentially of a major proportion of a base oil of petroleum origin and. a minor proportion about 0.1 to about 10 percent by weight of an ester product of malic acid in which about 50-100 mole percent of the radicals attached to the carbonyl carbon atoms through oxygen are radicals of hydroabietyl alcohol and the balance is a radical of a monohydric aliphatic alcohol having 8-20 carbon atoms.
• a novel composition of matter consisting essentially of a major proportion of a base oil of petroleum origin and a minor proportion efiective to increase the oiliness of said base oil of a mixture of hydrogenated rosin hydrocarbons and an ester product of malic acid in which about 50-100 mole percent of the radicals attached to the carbonyl carbon atoms through oxygen is radicals of hydroabietyl alcohol and the balance is a radical of a monohydric aliphatic alcohol having 8-20 carbon atoms.
• a novel composition of matter comprising:
• a novel composition of matter comprising:
• a novel composition of matter consisting essentially of a base oil of petroleum origin and a minor proportion about 0.1 to about 10 weight per cent of a mixture of 1) a half ester of malic acid and hydroabietyl alcohol and (2) a half ester of malic acid and an aliphatic monohydric alcohol having 8-20 carbon atoms in the molecule.
• a novel composition of matter consisting essentially of a base oil of petroleum origin and a minor proportion about 0.1 to about 10 weight per cent of a mixture of (1) a half ester of malic acid and hydroabietyl alcohol and (2) a half ester of malic acid and an aliphatic monohydric alcohol having 8-20 carbon atoms in the molecule, said mixture of said half esters having been heated until ester exchange occurs.
• Viscosity SUV (see) At 130' F. At 210 F.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Lubricants (AREA)

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Citations (5)

• 0
  • NL NL68899D patent/NL68899C/xx active
• 1949
  • 1949-04-08 US US86382A patent/US2564634A/en not_active Expired - Lifetime
• 1950
  • 1950-01-17 GB GB1243/50A patent/GB689242A/en not_active Expired

Patent Citations (5)

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