US2579037A - Lubricating composition - Google Patents

Lubricating composition Download PDF

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Publication number
US2579037A
US2579037A US63843A US6384348A US2579037A US 2579037 A US2579037 A US 2579037A US 63843 A US63843 A US 63843A US 6384348 A US6384348 A US 6384348A US 2579037 A US2579037 A US 2579037A
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oil
salt
lubricating composition
metal
test
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Evans Elliott Alfred
Elliott John Scotchford
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CC Wakefield and Co Ltd
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CC Wakefield and Co Ltd
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    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—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
    • 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
    • C10M141/10—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 phosphorus-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
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased 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
    • 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
    • C10M2223/042—Metal salts thereof
    • 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
    • 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
    • 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
    • C10N2010/06—Groups 3 or 13
    • 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
    • C10N2010/08—Groups 4 or 14
    • 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
    • C10N2010/12—Groups 6 or 16
    • 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
    • C10N2010/14—Group 7
    • 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
    • C10N2010/16—Groups 8, 9, or 10

Definitions

  • the present invention comprises improvements in or relating to lubricating compositions and relates more particularly, though not exclusively, to lubricating compositions for use in internal combustion engines which may be either petrolor oil-operated. In the latter case the invention is applied to the so-called heavy duty lubricating oils employed in diesel or other types of oil engines.
  • the present invention contemplates the use in a lubricating composition of a metallic derivative of an organic substituted dithiophosphate.
  • additives are known in general to impart to the oil good resistance to oxidation and to inhibit to a greater or less extent the formation of products corrosive to composite metal bearings.
  • Some of them also possess detergent or sludge dispersive properties, especially effective in this connection being the alkaline earth metal salts of the straight chain dithiophosphoric acids having ten or more carbon atoms.
  • salts of metals of groups 2 and 3 of the periodic table are especially effective, but the salts of other metals are also very satisfactory additives from the point of view of this invention especially as regards the inhibition of oxidation and corrosion of composite metal bearings.
  • a, lubricating composition comprises a lubricating oil base and a minor proportion of a metal salt (which is soluble in the oil base) of an organic (ii-substituted dithiophosphoric acid derived at least in part from a saturated aliphatic hydroxyether.
  • a metal salt which is soluble in the oil base
  • organic (ii-substituted dithiophosphoric acid derived at least in part from a saturated aliphatic hydroxyether ii-substituted dithiophosphoric acid derived at least in part from a saturated aliphatic hydroxyether.
  • n represents the valency of a metal M
  • R1 is a saturated aliphatic radicle containing an ether grouping
  • R2 is any suitable organic radicle.
  • One type of metal salt of the above character incorporated in a lubricating oil base in accordance with the present invention is one derived from tetrahydrofurfuryl alcohol, i. e., a salt in which radicle R1 of the above formula is a tetrahydrofurfuryl radicle represented by the formula CH2--CH1 -H: CH2
  • the radicle R2 is then some other suitable organic radicle since the dietetrahydrofurfuryl dithiophosphates are found to be insoluble in a lubricating oil base.
  • Examples of other aliphatic hydroxy-ethers from which the metal salt may be derived are: Ethylene glycol monobutyl ether (C4H9OCH2CII2OH), diethylene glycol monoethyl ether (C2H5OCH2CH2OCH2CH2OH), 3- methoxy-n-butanol, and triethylene glycol monobutyl ether.
  • Examples of organic hydroxylic compounds from which the radicle R2 of the above formula may be suitably derived are:
  • radicles for R1 and R2 in the general formula quoted above will always be such that the (ii-substituted metal salt is soluble in the lubricating oil base.
  • the radicle Ra should possess at least 5 carbon atoms.
  • disubstituted dithiophosphoric acids a metal salt of which is employed in accordance with the invention are: Tetrahydrofurfuryl octyl-cresyl dithiophosphoric acid and di-(p-butoxyethyl) dithiophosphoric acid.
  • the soluble metal salts may be employed of any of the following metals: barium, calcium, strontium, magnesium, zinc,-a luminium, nickel, cobalt, tin, cadmium, chromium, manganese and thallium.
  • a proportion of from 0.2% to 2.0% by weight of the metal salt is employed in the lubricating composition; and in one form of the invention the lubricating composition in- *i :cludes' also a small proportion of an oil-soluble metal salt'of a petroleum sulphonic acid.
  • the latter component may conveniently be added in a proportion of from 0.05% to 2.0% by weight of the composition. More particularly in the case where a chromium dithiophosphate is employed the conjoint use of tin petroleum sulphonate is preferred.
  • metal salts contemplated in this invention have only a limited degree of solubility in mineral oil. True solutions of such compounds may, however, be obtained by dissolving them first in concentrated oil solutions of the metal petroleum sulphonates and then eifecting solution in the mineral oil in the desired proportion. 7
  • Examples of compounds with a limited oil-solubility which may be solubilised in this way are Zinc salt of di(2-butoxy2ethoxyethyl)dithiophosphoric acid Calcium salt of di(p-butoxyethyl) Cobalt salt of 2methoxy -2-ethoxyethyl methyl cyclohexyl dithiophosphoric acid It is, however, preferred to employ salts which weight in the region of 400-500. Any polyvalent metal petroleum sulphonate, or mixtures thereof may be employed, special preference being given to the tin salts. Other metal salts may however be used with beneficial results e. g. those of calcium, barium, strontium, magnesium, aluminium, chromium, manganese, cadmium, nickel, cobalt, zinc and thallium.
  • metal petroleum sulphonates and the metal dithiophosphates of this invention provides lubricants possessing excellent detergent properties, such lubricants being especially suitable as heavy duty lubricants for use in high-speed diesel engines where high loads and piston temperatures are encountered.
  • Preparation of the metal salt of the di-substituted dithiophosphoric acid is conveniently effected by first reacting the aliphatic hydroxyether with phosphorus pentasulphide, and Where a mixed organic dithiophosphate is desired an appropriate hydroxylic organic compound may be admixed with the hydroxyether for simultaneous reaction with the phosphorus pentasulphide.
  • the acid may be neutralised by caustic soda and. a desired metal salt produced by the addition of a suitable salt of the said metal.
  • Example I -P1-eparation of chromium tetfahydrofurfur'yl octyl-cresyl dithiophospihate 772 gms. of tetrahydrofurfuryl alcohol were mixed with .1650 gms. of octyl cresol'ina 5-litre flask, heated to 130? C., and treated with 915 gms. of powdered phosphorus pentasulphide added in small quantities with stirring, The
  • the residual free acid may be substantially neutralised by heating the product (preferably in oil solution) with a metal oxide or hydroxide (such as zinc oxide or calcium or barium hydroxide) to produce, for example, a mixture of chromium and zinc salts associated with a minor amount of sodium salt.
  • a metal oxide or hydroxide such as zinc oxide or calcium or barium hydroxide
  • Example II Preparation of zinc di butoxyethyl) dithiophosphate tered, and the solvent removed by distillation.
  • the acidity of the product corresponded to a molecular weight of 370 (calculated 330) i. e. conversion to the dithiophosphate was 88% complete.
  • the zinc salt was clear pale yellow liquid readily soluble in oil.
  • Example 11 The product of Example 11 is represented by the formula clmocmcmo s P ⁇ Zn olmoomomo s
  • Example III A lubricating composition was produced by in corporating in a mineral lubricating oil base 0.8% by weight of the product of Example I and 0.2% of tin petroleum sulphonate.
  • Example IV Preparation of cadmium "dim-butozryethyl) dithiophosphate 33.5 grams of di(,c-butoxyethyl) dithiophosphate prepared as described in Example II were mixed with 636.5 cos. of water and caustic soda added gradually with stirring at room temperature until neutralisation was complete. The solution was filtered from a little insoluble material, heated to 50 C. and treated with a warm 10 per cent solution containing 12.5 grams of cadmium chloride, when the cadmium. salt was precipitated as a yellowish-white crystalline solid.
  • Example V Preparation of zinc salt of 3-methioaty-n-butyl Z-ethyl hexyl dithiophosphoric acid
  • Example II there were obtained from the reaction between a mixture of 32.5 grams of 2-ethyl hexanol and 26 grams of 3-methoxy-n-butanol with 27.8 grams of phosphorus pentasulphide during 15 minutes at -110 C. and finally 5 minutes at C., 75 grams of 2-ethyl hexyl 3-methoxy-n-buty1 dithiophosphoric acid, representing a 91% yield.
  • the molecular weight was 375, as compared with a theoretical value of 328.
  • Example V is generally ap' plicable for the preparation of the zinc and magnesium salts contemplated by this invention, the method of Example IV being more widely applicable to the salts of any of the polyvalent metals.
  • Other known methods may, however, be adopted, e. g. direct reaction between the'free acid and a metal oxide in alcohol-benzene solution at 40-50" C. (applicable especially to the alkaline earth metal and magnesium salts) or direct reaction between a metal hydroxide, such as barium hydroxide, and free acid by heating together in mineral oil solution in presence of a current of air to remove liberated water.
  • metathesis may be carried out in alcoholic solution between an alkali metal salt of a dithiophosphoric acid and an alcohol-soluble metal salt.
  • Example V The product of Example V is represented by the formula onlomomcmonomo S TEST RESULTS Test 1.O:m'dation resistance I
  • Lubricating compositions were oxidised under the standard conditions of the British Air Ministry oxidation test except that a temperature of 160 C. was employedand that a copper catalyst, consisting of a rolled polished piece of copper foil 2 x 1", waspresent. The catalyst was replaced by a fresh one at the end of the first period of 6 hours oxidation.
  • Copper strips, as catalysts, /2" wide and bent into a semicircle 3%,” in diameter were placed wholly below the surface of the lubricant and attached by means of vertical'copper wires to corks fitted in the beaker covers. Each beaker was also fitted with a thermometer.
  • Additives marked with an asterisk were not soluble in mineral oil in the proportions employed in the absence of the metal petroleum sulphonate.
  • Oil A as employed in these and in ensuing tests consisted of a blend of 94% of a solvent refined parafiinic type mineral oil of viscosity about 150 seconds Redwood at 140 F. and 6% of a blend of viscosity about 330 seconds Redwood at 140 F. containing a brightstock.
  • Test 2 Bearing corrosion The following test was employed for obtaining information as to the tendency for corrosion of composite metal bearings, particularly copperlead bearings, to occur in use of lubricating compositions provided by the invention.
  • This compound contained about 72% of actual chromium salt.
  • Test 3 A simple test was devised to compare the tendencies of oils to deposit gum, lacquer and carbon on hot metal surfaces such as piston walls and heads in internal combustion engines.
  • Rectangular aluminium blocks (12" x 2" x A) were cleaned by rubbing with pumice and water and finally by washing with petroleum ether. They were then clamped in a special holder at an angle of 25 to the horizontal and heated at the upper end by means of a Bunsen burner.
  • the oil under test was now dropped from a burette on to the block at a point, the temperature of which was 350 C., (as measured by a pyrometer). at a rate of approximately 1 cc. per minute for a total of 30 minutes, after which the block was allowed to cool and washed free from L oil with petroleum ether.
  • a heavy black deposit of carbon A dark. brown deposit of lacquer. A light brown deposit of lacquer.
  • (1) and (2) correspond to a rating of on the Lausonpiston rating chart, (3) to a rating of about 4, and (4) to a rating of about 1.
  • Oil B was a solvent refined parafiinic type mineral oil of viscosity about 150 seconds Redwood at 140 F.
  • Test 4 was carried out in standard H-2 type Lauson engines, under the following conditions:
  • Test results were as follows:
  • the C. R. C. visual rating was according to the method laid down by the Co-ordinating Research 7 Council for rating piston cleanliness in the standard Chevrolet 36-hour L-4 test, in which a clean piston would have a rating of 10.0.
  • Test 5.36-.hour Chevrolet test Tests were carried out on a ,G-cylinder Chevrolet engine of standard type and according to the Standard Co-ordinating Research Council procedure L-4.
  • a lubricating composition comprising as a major ingredient a mineral oil base, said base having incorporated therein as an additive a small amount, sufficient to inhibit bearing cor-;
  • R1 is a saturated radical free from aromatic substituents and containing an ether grouping and is selected from the group consisting of aliphatic radicals and heterocyclic radicals containing only carbon and oxygen in the nucleus and R2 is an organic radical having at least 5 carbon atoms and is selected from the group consisting of saturated aliphatic radicals, saturated aliphatic radi-p cals having an ether grouping, saturated alicyclic radicals, saturated heterocyclic radicals having only carbon and oxygen in the nucleus and alkylated benzene radicals in which the alkyl substituent is saturated.
  • composition in accordance with claim 1 in which the composition also contains a small amount, suificient to increase the detergent properties of the composition, of an oilsoluble metal salt of petroleum mahogany sulphonic acid.
  • a lubricating composition in accordance with claim 7 in which the amount of said salt of petroleum sulphonic acid is between 0.05 and 2.0 by weight of the mineral oil base.
  • a lubricating composition in accordance with claim 7 in which the amount of the metal salt of an organic dithiophosphorlc acid is between 02 and 2.0% by weight of the mineral oil base and the amount of the metal salt of petroleum sulphonic acid is between 0.05 and 2.0% by weight of the mineral oil base.

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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)
US63843A 1947-12-09 1948-12-06 Lubricating composition Expired - Lifetime US2579037A (en)

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GB277989X 1947-12-09
GB41148X 1948-11-04

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2838555A (en) * 1951-10-12 1958-06-10 Lubrizol Corp Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids
US2905683A (en) * 1952-12-17 1959-09-22 Lubrizol Corp Ether containing esters of dithiophosphoric acid and salts thereof
US3243482A (en) * 1962-01-10 1966-03-29 Gen Aniline & Film Corp Surface-active thiophosphoric acid esters of polyglycol ethers
US5919740A (en) * 1998-05-29 1999-07-06 Exxon Chemical Patents Inc Alkylthiophosphate salts for lubricating oils

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BE503233A (enrdf_load_html_response) * 1950-05-12
NL85589C (enrdf_load_html_response) * 1951-03-29
DE961484C (de) * 1952-12-18 1957-04-04 Exxon Research Engineering Co Verfahren zur Erhoehung des Viskositaetsindex von Schmieroelen
GB801151A (en) * 1955-01-27 1958-09-10 Lubrizol Corp Gear lubricant improving agents
US2824063A (en) * 1956-05-11 1958-02-18 Sinclair Refining Co Lubricating oils containing a zinc dithiophosphate and nickel mahogany sulfonate
US3000822A (en) * 1957-01-22 1961-09-19 Lubrizol Corp Phosphorodithioate inhibitors
US2916448A (en) * 1957-05-31 1959-12-08 Sinclair Refining Co Oxidation inhibitor-detergent material
US3070546A (en) * 1959-01-16 1962-12-25 Lubrizol Corp Nitrogen-, phosphorus- and sulfurcontaining lubricants
DE1245013B (de) * 1960-05-12 1967-07-20 Sineclair Refining Company Mineralschmieroel
US4042323A (en) * 1972-07-17 1977-08-16 Petrolite Corporation Process of inhibiting corrosion of metal in an aqueous environment with mixtures of thio-, oxygen and thio- oxygen phosphates and pyrophosphates
US3909447A (en) * 1972-07-17 1975-09-30 Petrolite Corp Mixtures of thiophosphates, oxygen phosphates and pyrophosphates
CN113680535B (zh) * 2021-08-24 2023-03-21 中南大学 一种烷基醚基二硫代磷酸盐捕收剂及其制备方法与应用

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US2125936A (en) * 1936-03-03 1938-08-09 Sonneborn Sons Inc L Lubricating oil
US2241243A (en) * 1939-03-25 1941-05-06 Texas Co Lubricating oil
US2252984A (en) * 1939-05-06 1941-08-19 Standard Oil Co Compounded hydrocarbon oil
US2344395A (en) * 1942-06-16 1944-03-14 American Cyanamid Co Lubricating oil
US2369632A (en) * 1941-11-13 1945-02-13 American Cyanamid Co Lubricating oils
US2372244A (en) * 1941-09-24 1945-03-27 Standard Oil Co Esters of acids of phosphorus
US2382775A (en) * 1942-06-16 1945-08-14 American Cyanamid Co Dithiophosphoric acids and salts thereof
US2417876A (en) * 1944-08-16 1947-03-25 Tide Water Associated Oil Comp Inhibited oil
US2418422A (en) * 1944-12-11 1947-04-01 Sinclair Refining Co Lubricant

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US2905683A (en) * 1952-12-17 1959-09-22 Lubrizol Corp Ether containing esters of dithiophosphoric acid and salts thereof
US3243482A (en) * 1962-01-10 1966-03-29 Gen Aniline & Film Corp Surface-active thiophosphoric acid esters of polyglycol ethers
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FR976342A (fr) 1951-03-16
NL70344C (enrdf_load_html_response)
DE832030C (de) 1952-02-21
GB658183A (en) 1951-10-03
CH277989A (de) 1951-09-30
FR976343A (fr) 1951-03-16
US2579038A (en) 1951-12-18
NL69724C (enrdf_load_html_response)
GB658182A (en) 1951-10-03

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