US2476972A - Mineral oil composition - Google Patents

Mineral oil composition Download PDF

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US2476972A
US2476972A US709930A US70993046A US2476972A US 2476972 A US2476972 A US 2476972A US 709930 A US709930 A US 709930A US 70993046 A US70993046 A US 70993046A US 2476972 A US2476972 A US 2476972A
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oil
soluble
mineral oil
per cent
phosphorus
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Everett W Fuller
Ellwood M Johnson
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ExxonMobil Oil Corp
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Socony Vacuum Oil Co Inc
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Priority to US709930A priority patent/US2476972A/en
Priority to GB23475/47A priority patent/GB645267A/en
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Priority to DES19742A priority patent/DE898066C/de
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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
    • 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
    • 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
    • C10M2219/04—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
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • 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
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to a novel mineral oil composition and, more particularly, is concerned with a mineral oil composition containing minor proportions of an oil-soluble detergent and of an oil-soluble, phosphorusand sulfur-containing reaction product.
  • mineral oils generally possess one or more undesirable characteristics which limit their use.
  • One such characteristic ls their instability under operating conditions normally encountered in present day engines, such that within a relatively short time, metal engine parts become contaminated with sludge. lacquer and resinous materials. In most instances, these contaminants are deposited on and about piston rings causing them to stick, the phenomenon being referred to in the art as ring-sticking.” As a. consequence of this instability of the mineral oils, engine operating efliciency is seriously reduced.
  • Another undesirable characteristic of mineral oils is their tendency to oxidize producing acidic materials. These acidic materials corrode metal engine parts, particularly alloy bearings such as those of the cadmium-silver, copper-lead, etc., type.
  • oil-soluble metal sulfonates as addition agents for mineral oils has been suggested, and they have been, found to be satisfactory from the standpoint of imparting detergent properties to mineral oils.
  • oil-soluble sulfonates fail to improve, and in some cases even impair, other characteristics of mineral oils.
  • oil-soluble metal sulfonates have increased the formation of acidic materials in mineral oils during use, thus inducing corrosion of metal parts with which the mineral oils come in Contact.
  • oil-soluble magnesium sulfonates when used in combination with an oil-soluble phosphorusand sulfur-containing reaction product of a dicyclic terpene and a phosphorus sulfide, are particularly effective in improving the corrosion and oxidation characteristics of mineral oils.
  • mineral oils containing an oil-soluble magnesium sulfonate and an oil-soluble phosphorusand sulfur-containing reaction product of a dicyclic terpene and a phosphorus sulde are extremely stable and possess outstanding detergent, oxidation and corrosion characteristics, and that oil-soluble magnesium sulfonates are appreciably more eifective in this connection, than other oil-soluble metal sulfonates both from the standpoint of weight per v cent of metal, and from the standpoint of mole per cent of metal which must be present in the mineral oil in order to effect the desired improvements in the characteristics thereof.
  • the use of magnesium salts has the inherent added advantage of introducing relatively small amounts of metal in mineral oils which means low ash contents when the oil is burned.
  • an object of the present invention to provide an improved mineral oil composition.
  • Another object is to provide a mineral oil composition possessing improved detergent, oxidation and corrosion characteristics.
  • An important object is to afford a mineral oil concentrate containing a mineral4 oil in combination with an oil-soluble magnesium sulfonate and an oil-soluble phosphorusand sulfur-containing reaction product of a phosphorus sulde with a dicyclic terpene.
  • a more specific object is to provide a mineral oil composition having improved vcharacteristics which comprises in combination,
  • Figure 1 shows a series of curves representing graphically the relationship between they E. C. (engine cleanliness) rating of various oil blends containing anoil, 0.75% by weight of a pinenephosphorus pentasulde reaction product, and varying amounts of yvarious metal diwax phenyl sulfonates, and the weight per cent of metal in the oil blends; and
  • Figure 2 shows a series of curves representing graphically the relationship between the E. C. rating of various oil blends containing an oil, 0.75% by weight of 'a pinene-phosphorus pentasulde reaction product and varying amounts of various metal diwax phenyl sulfonates, and the mole per cent of metal in the oil blends.
  • the present invention provides a mineral oil composition
  • a mineral oil composition comprising a. viscous mineral oil fraction having in admixture therewith: an'oil-soluble magnesium sulfonate, and an oil-soluble, phosphorusand sulfur-containing reaction product obtained by reaction between I a phosphorus sulfide and a dicyclic terpene.
  • oil-soluble magnesium sulfonates are contemplated herein.
  • Typical of oil-soluble magnesium sulfonates are those obtained from aromatic hydrocarbons or substituted aromatic hydrocarbons, and a sulfonating agent such as strong sulfuric' acid, oleum, chlorsulfonic acid and the like.
  • Other typical sulfonates are those obtained by treatment of parains, naphthenes and various petroleum fractions-paranic, naphthenic or aromatic-with the same reagents. Preferred, however.
  • magnesium salts of sulfonic acids of wax-substituted benzene and y naphthalene wherein the wax substitutent is a long-chain aliphatic hydrocarbon group containing at least about eighteen carbon atoms and is obtained from paraflin wax.
  • the basic magnesium salts of diwax-benzene sulfonate are especially preferred.
  • EXAMPLE 1 Preparation of the basic magnesium salt of diwax-phenyl sulfonic acid A paraiiin wax having an average of 24 carbon atoms per molecule and a. melting point of 126 F. was chlorinated ata temperature of about 100 C. with chlorine gas until the Weight of the wax had increased about 12%. The chlorowax thus obtained was then blown with nitrogen to remove any occluded chlorine and hydrogen chloride.
  • the oil-soluble, phosphorusand sulfur-containing reaction products contemplated herein are those obtained by reacting a dicyclic terpene and a phosphorus sulde at a temperature above about C.
  • any one of the several phosphorus sulfides such as PaSe (or PS2), P4Sn (0r P2S3) P483, P2Ss (0r P4810), P4S'l, etc., may be used in the preparation of the said reaction products, particularly preferred are those reaction products obtained using PaSs.
  • Dicyclic terpenes are defined herein as those terpenes which are characterized by the presence of one double bond in the molecule and which are comprised of two ring systems. Typical of such terpenes are pinene, camphene and fenchene.
  • contemplated as coming within this particular designation are those materials which are predominantly comprised of one or more dicyclic terpenes; representative of such materials are the essential or volatile oils which are predominantly comprised of such a terpene, or terpenes, and are typified by turpentine oil, the predominant constituent of which is pinene.
  • Preferred of the dicyclic terpene reactants are pinene and turpentine oil. Accordingly, the preferred reaction products are those obtained from Piss and pinene, and P255 and turpentine oil.
  • the reaction between phosphorus pentasulde and pinene commences at about 100 C. and is exothermic in nature. During the reaction, the reaction mixture increases appreciably in viscosity and little, if any, hydrogen sulde is evolved therefrom.
  • the reaction product obtained in this reaction contains phosphorus and sulfur in substantially the same amounts as are added through the particular phosphorus suliide used. It would appear, then, that the reaction is one of addition, that is, addition of the prosphorus suliide to the oneV unsaturated bond present in pinene.
  • reaction temperature for the reaction described above should be one of at least about 100 C.
  • preferred temperatures fall within the range of about 100 C. to about 160 C.
  • the proportions of reactants used herein may be varied in order to prepare reaction products having different degrees of oil solubility and different degrees of oil-improving power. It is preferred, however, to use about 1 mol of a phosphorus sulfide With 4 mols of a dicyclic terpene for the preparation of a reaction product readily soluble in petroleum oils.
  • a viscous gel-like reaction product is obtained which is difliculty soluble in petroleum oils.
  • less than 1 mol of Pass is used with 4 mols of pinene, a viscous oil somewhat insoluble in mineral oils is obtained after the unreacted pinene has been recovered by distillation.
  • agents of the type contemplated herein can be obtained by using different ratios of reactants, particularly preferred improving agents are those obtained by using approximately 1 mol of a phosphorus sulde for every 4 mols of a dicyclic terpene.
  • the oil compositions contemplated herein may also contain, in addition to an oil detergent and a dicyclic terpene-phosphorus sulfide reaction product, a small amount of one or more other oil-soluble, phosphorusand sulfur-containing reaction products.
  • One such reaction product is that which is obtained by reaction of approximately one mol of phosphorus pentasulde with four mols of oleyl alcohol, or ocenol, at a temperature falling Within the range varying between about 125 C. and about 150 C., for a relatively short time.
  • These reaction lproducts are described in further detail in copending application Serial Number 524,490, iled February 29, 1944, now U. S. Patent No. 2,411,153, issued November 19, 1946, of Everett W. Fuller et al.
  • Another such reaction product is that which'is obtained by reacting a cycle stock with about 5-15% by weight of phosphorus pentasuliide.v
  • the following test results are provided to demonstrate the properties of mineral oils containing small amounts of metal sulfonates, other .than magnesium sulfonates, oil detergents and of the aforementioned dicyclic terpene-phosphorus sulde reaction products, and "the outstandingly superior properties of mineral oils containing small amounts of the magnesium sulfonate oil detergents and of the aforementioned dicyclic terpene-phosphorus suliide reactionV products.
  • the metal sulfonates, other than magnesium sulfonates were prepared by reacting the diwaxphenyl sulfonic acid obtained in accordance with the procedure set forth in Example 1, with the proper metal hydroxide or chloride in accordance with the procedures outlined in Examples 1 and 2.
  • the mineral oil compositions of this invention may also contain one or more other oil-soluble, phosphorusand sulfur-containing reaction products, such as those obtained from cycle stocks and Pass, and' oleyl alcohol and Pass, all as dened above. Oils of excellent quality are obtained with from labout l 0.10% to about 3.0% of such s. reaction product,
  • Mineral oil concentrates are also contemplated herein, such concentrates containing substantially larger concentrations of amagnesium sulfonate oil detergent and of a dicyclic lterpenephosphorus sulfide reaction product, than those piston and lower ratings indicating increasing enumerated abQVe- That iS, TelatiVely large amounts of deposits.
  • Table II The pertinent data of each run are tabulated in Table II.
  • these mineral oil concentrates may also contain one or more of the aforesaid other oil-soluble, phosphorusand sulfur-containing reaction products, such as those obtained that on a per cent by weight basis of comparison, from oleyl alcohol or a cycle stock, in .amounts the magnesium-containing detergents are superior to the other metal suli'onates. This superiority is particularly marked in the case of the basic magnesium sulfonates. When the comparisubstantially in excess of those described above.
  • an oil-soluble magnesium sulfonate and a dicyclic terpeneson is made on the basis 0f per cent of metal in 55 phosphorus sulde reaction product, as defined hereinbefore, may be incorporated in a mineral oil in any one of several ways.
  • the oil-soluble magnesium sulfonate and a dicyclic terpeneson is made on the basis 0f per cent of metal in 55 phosphorus sulde reaction product, as defined hereinbefore, may be incorporated in a mineral oil in any one of several ways.
  • dicyclic terpene reaction product may be added to an oil fraction containing .an oil-soluble magnesium sulfonate; also .an oil-soluble magnesium sulfonate may be added to the reactants (dicyclic terpene and phosphorus sulde) used in the preparation of the said reaction product and, in such case, will be present during the reaction.
  • concentrations of from about 0.5 per cent to about 10 per cent of a magnesium-containing oil defonate may react with the dicyclic terpene and phosphorus sulde to form a complex reaction product under the reaction conditions enumerated herein; the product obtained in this manner tergent are used in an oil fraction, but coi'icen- ⁇ 70 may then be added to an oil fraction.
  • Accordtrations of the order of about 2% have been found to,be satisfactory for most purposes.
  • an oil-soluble magnesium sulfonate and a reaction product of the aforesaid type may enter into chemical reaction when the oil composition is used as a lubricant under certain conditions, such forexample, as a lubricant in an engine operating at relatively high temperatures.
  • mineral oil composition as used herein, and as recited in all of the appended claims, isinclusive of all mineral oil fractions containing an oil-soluble magnesium sulfonate and' a dicycllc terpenephosphorus sulfide reaction product of the type deilned hereinbefore, in the concentrations previously enumerated, and is inclusive of oil compositions obtained or prepared by any of the aforesaid several procedures.
  • mineral oil concentrate is inclusive o! all mineral oil fractions containing relatively large amounts of the said oil-soluble magnesium sulfonates and said reaction product.
  • magnesium diwax phenyl sulfonates are preferred, al1 other oil-soluble magnesium sulfonates coming within the deiinition herein of a magnesium-containing oil-detergent may be used.
  • the mineral oil fraction disclosed herein is but typical of the mineral oil fractions which may be used.
  • An improved mineral oil composition comprising a viscous mineral oil fraction having in admixture therewith a minor proportion, from about 0.5 per cent to about 5.0 per cent, of an oil-soluble magnesium sulfonate; and a minor proportion, from about 0.10 per cent 'to about 3.0 per cent, of an oil-soluble. phosphorusand sulfur-containing reaction product obtained by reaction of substantially one mol of a phosphorus sulfide with four mols of a material selected from the group consisting of a dicyclic terpene and an essential oil predominantly consisting of a dicycllc terpene, at a temperature varying between about 100" C. and about 160 C.
  • An improved mineral oil composition comprising a. viscous mineral oil fraction having in admixture therewith a minor proportion, from about 0.5 per cent to about 5.0 per cent, of an oilsoluble magnesium sulfonate; ⁇ and a minor proportion, from about 0.10 per cent to about 3.0 per cent, of an oil-soluble, phosphorusand sulfurcontaining reaction product obtained by reaction of substantially one mol of phosphorus pentasulde and four mols of a material selected from the group consisting of a dicyclic terpene and an essential oil predominantly consisting of a dicycllc terpene, at a temperature varying between about 100 C. and about 160 C.
  • An improved mineral oil composition comprising a viscous mineral oil fraction having in admixture therewith a minor proportion, from about 0.5 per cent toabout 5.0 per cent, of an oilsoluble magnesium salt of a wax-substituted aromatic sulfonic acid; and a minor proportion, from about 0.10 per cent to about 3.0 per cent, of an oil-soluble, phosphorusand sulfur-containing reaction product obtained ⁇ by reaction of substantially one mol of a phosphorus sulfide with four mols of a material V ⁇ selected from the group consisting of a dicycllc terpene and an essential oil predominantly consisting of a dicycllc terpene, at a temperature varying between about 100 C. and about 160 C.
  • An improved mineral oil composition comprising a viscous mineral oil fraction having in admixture therewith a minor proportion, from about 0.5 per cent to about 5.0 per cent, of an oilsoluble magnesium salt of a wax-substituted aromatic sulfonic acid; and a minor proportion, from about 0.10 per cent to about 3.0 per cent, of an oil-soluble, phosphorusand sulfur-containing reaction product obtained by reaction of substan- 1 tially one mol of phosphorus pentasulde and Cil four mols of a material selected from the group consisting of a dicycllc terpene and an essential oil predominantly consisting of a dicyclic ter-4 soluble magnesium salt of a wax-substituted benzene sulfonic acid; and a minor proportion, from about 0.10 per cent to about 3.0 per cent, of an oilsoluble, phosphorusand sulfur-containing reaction product obtained by reaction o1' substantially one mol of a phosphorus sulilde with four mols of
  • An improved mineral oil composition comprising a viscous mineral ,oil fraction having in admixture ⁇ therewith a minor proportion, from about 0.5 per cent to about 5.0 per cent, of an oilsoluble magnesium salt of a. wax-substituted benzene sulfonic acid; and a minor proportion, from about 0.10 per cent to about 3.0 per cent, of an oilsoluble, phosphorusand sulfur-containing reaction product obtained by reaction of substantially one mol of phosphorus pentasulfide and four mols of a material selected from the group consisting of a dicycllc terpene and an essential oil predominantly consisting of a dicycllc terpene. at a temperature varying between about 100 C. and about C.
  • An improved mineral oil composition comprising a viscous mineral oil fraction having in admixture therewith a minor proportion, from about ,0.5 per v'cient-.15b about 5.0 per cent, of an oil-soluble magnesium salt of a diwax-substituted benzene sulforiic acid; and a minor proportion, from about 0.10 per cent to about 3.0 percent, of an oil-soluble, phosphorusand sulfur-containing reaction product obtained by reaction of substantially one mol of a phosphorus sulfide with four mols of a material selected from the group consisting of a dicyclic terpene and an essential oil predominantly consisting of a dicycllc terpene, at a temperature varying between about 100 C. and about 160 C.
  • An improved mineral oil composition comprising a viscous mineral oil fraction having in admixture therewith a minor proportion, from about 0.5 per cent to about 5.0 per cent, of an oil- 11 soluble magnesium salt of a diwax-substituted benzene sulfonic acid; and a minor proportion, from about 0.10 per cent to about 3.0 per cent, of an oil-soluble, phosphorusand sulfur-containing reaction product obtained by reaction of substantially one mol of phosphorus pentasulde and four mols of a material selected from the group consisting of a dicyclic terpene and an essential oil predominantly consisting of a dfcylic terpene.:
  • V A At a temperature varying between about 100 C. and about 160 C.
  • An improved.- mineral oil composition comprising a. viscous mineral oll fraction having in admixture therewith a minor proportion, from ⁇ 10.
  • An improved mineral oil composition comprising a viscous mineral oil traction having in admixture therewith va minor proportion, from about 0.5 per cent to about 5.0 per cent, of an oil-soluble basic magnesium salt of a diwaxsubstituted benzene sulfonlc acid; and a minor proportion, from about 0.10 per cent to about 3.0 per cent, of an oil-soluble, phosphorusand sulfur-containing reaction product obtained lby reaction of substantially one mol of phosphorus pentasultlde and four mols of a material selected from the group consisting of a dicylic terpene and an essential oil predominantly consisting of a dicyclic terpene, at a temperature varying between about 100 C. and about 160 C.

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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)
US709930A 1946-11-15 1946-11-15 Mineral oil composition Expired - Lifetime US2476972A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL71357D NL71357C (enrdf_load_stackoverflow) 1946-11-15
FR955566D FR955566A (enrdf_load_stackoverflow) 1946-11-15
US709930A US2476972A (en) 1946-11-15 1946-11-15 Mineral oil composition
GB23475/47A GB645267A (en) 1946-11-15 1947-08-25 Mineral oil composition
DES19742A DE898066C (de) 1946-11-15 1950-09-28 Schmiermittel und Verfahren zu ihrer Herstellung

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GB (1) GB645267A (enrdf_load_stackoverflow)
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE947416C (de) * 1951-01-29 1956-08-16 Bataafsche Petroleum Schmieroelmischungen, insbesondere auf Mineraloelbasis
US2969324A (en) * 1958-02-20 1961-01-24 Exxon Research Engineering Co Phosphosulfurized detergent-inhibitor additive
US3132101A (en) * 1956-05-21 1964-05-05 Sinclair Research Inc Detergent and anti-oxidant lubricant

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2379453A (en) * 1944-06-01 1945-07-03 Socony Vacuum Oil Co Inc Mineral oil composition
US2402325A (en) * 1943-08-19 1946-06-18 Atlantic Refining Co Oil solutions of basic alkaline earth metal sulphonates and method of making same
US2416281A (en) * 1944-06-09 1947-02-25 Socony Vacuum Oil Co Inc Mineral oil composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2402325A (en) * 1943-08-19 1946-06-18 Atlantic Refining Co Oil solutions of basic alkaline earth metal sulphonates and method of making same
US2379453A (en) * 1944-06-01 1945-07-03 Socony Vacuum Oil Co Inc Mineral oil composition
US2416281A (en) * 1944-06-09 1947-02-25 Socony Vacuum Oil Co Inc Mineral oil composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE947416C (de) * 1951-01-29 1956-08-16 Bataafsche Petroleum Schmieroelmischungen, insbesondere auf Mineraloelbasis
US3132101A (en) * 1956-05-21 1964-05-05 Sinclair Research Inc Detergent and anti-oxidant lubricant
US2969324A (en) * 1958-02-20 1961-01-24 Exxon Research Engineering Co Phosphosulfurized detergent-inhibitor additive

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DE898066C (de) 1953-11-26
FR955566A (enrdf_load_stackoverflow) 1950-01-17
GB645267A (en) 1950-10-25
NL71357C (enrdf_load_stackoverflow)

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