EP0063631B1 - Detergent-Dispersant-Zusammensetzung für Schmier- und Heizöle - Google Patents

Detergent-Dispersant-Zusammensetzung für Schmier- und Heizöle Download PDF

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Publication number
EP0063631B1
EP0063631B1 EP81103229A EP81103229A EP0063631B1 EP 0063631 B1 EP0063631 B1 EP 0063631B1 EP 81103229 A EP81103229 A EP 81103229A EP 81103229 A EP81103229 A EP 81103229A EP 0063631 B1 EP0063631 B1 EP 0063631B1
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EP
European Patent Office
Prior art keywords
hydrotalcite
composition
dispersant
detergent
hydrophobic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP81103229A
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English (en)
French (fr)
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EP0063631A1 (de
Inventor
Shigeo Miyata
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Kyowa Chemical Industry Co Ltd
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Kyowa Chemical Industry Co Ltd
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Publication date
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Priority to EP81103229A priority Critical patent/EP0063631B1/de
Priority to DE8181103229T priority patent/DE3172108D1/de
Publication of EP0063631A1 publication Critical patent/EP0063631A1/de
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Publication of EP0063631B1 publication Critical patent/EP0063631B1/de
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Classifications

    • 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
    • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/10—Metal oxides, hydroxides, carbonates or bicarbonates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/12—Inorganic compounds
    • C10L1/1233—Inorganic compounds oxygen containing compounds, e.g. oxides, hydroxides, acids and 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/063—Peroxides
    • 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
    • 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

Definitions

  • This invention relates to a detergent-dispersent composition which is important as an additive to a lubricating or fuel oils. Specifically, it relates to a detergent-dispersant composition for lubricating or fuel oils which exhibits an outstanding overbasing ability, an excellent ability to maintain an ultrafinely dispersed state, has excellent affinity for, and dispersibility in, lubricating or fuel oils, can be blended by a very easy operation in use, and can exhibits an excellent detergent-dispersant effect.
  • FR-A-1 571 821 an additive for fuel oils is known, consisting essentially of a mixture of finely divided particles of partially dehydrated hydroxides of magnesium and aluminium and of a surfactant. It is also known from FR-A-2 371 408 that hydrotalcite is generally used as neutralising agent.
  • the object of the present invention is to provide a detergent-dispersant composition having superior properties as an additive to lubricating or fuel oils.
  • composition consisting essentially of
  • Detergent-dispersant compositions have been widely used as additives to lubricating or fuel oils in order to neutralize undesirable corrosive acidic pollutant substances resulting from oxidation or incomplete combustion of these oils and finely disperse the resulting insoluble substances in the oils thereby preventing these substances from being flocculated into a deposit which may cause various troubles, and also to maintain an engine clean and prevent rust formation at metallic parts which have low corrosion resistance.
  • Such a detergent-dispersant composition is used in combination with a hydrophobic (oil-soluble or oil-miscible) dispersant, a hydrophobic diluent, an overbasing agent and other additives.
  • a hydrophobic dispersant oil-soluble or oil-miscible dispersant
  • a hydrophobic diluent hydrophobic diluent
  • an overbasing agent and other additives.
  • it is frequently in the form of a fine colloidal dispersion composed of the hydrophobic dispersant and the overbasing agent dissolved in, or mixed with, the hydrophobic diluent.
  • the aforesaid overbasing agent is required to have an alkali value (AV) [the amount of milligrams of KOH per gram equivalent] of at least 250 per gram equivalent in the form of overbased sulfonate added to a hydrophobic dispersant, a hydrophobic diluent, etc.
  • AV alkali value
  • the detergent-dispersant composition while containing a basic compound having such an alkali value, should not cause flocculation, precipitation, separation, etc. of the basic compound and should be maintained in such an ultrafinely dispersed condition as not to be removed from lubricating or fuel oils in an in-line filtering device such as an automotive oil filter.
  • Such a conventional means requires a complex process which comprises mixing, for example, an oxide or hydroxide of magnesium, water and/or an alcohol, a dispersant such as an alkylbenzene sulfonate salt in a diluent oil, and a petroleum solvent, introducing carbon dioxide into the mixture until the oxide or hydroxide of magnesium is converted to a carbonate, and then removing water, the alcohol, the petroleum solvent and non-dispersed particles.
  • a complex process which comprises mixing, for example, an oxide or hydroxide of magnesium, water and/or an alcohol, a dispersant such as an alkylbenzene sulfonate salt in a diluent oil, and a petroleum solvent, introducing carbon dioxide into the mixture until the oxide or hydroxide of magnesium is converted to a carbonate, and then removing water, the alcohol, the petroleum solvent and non-dispersed particles.
  • the present inventors made investigations in order to remove the aforesaid defect and disadvantage in detergent-dispersant compositions for lubricating or fuel oils. These investigations have led to the discovery that a hydrotalcite untreated or surface-treated with an anionic surface-active agent, particularly a hydrotalcite of formula (1) with or without surface-treatment with, an anionic surface-active agent, which has not been suggested at all in conventional magnesium containing overbasing agents such as magnesium carbonate (Japanese Laid-Open Patent Publication No. 144404/1979), a basic complex of magnesium (Japanese Laid-Open Patent Publication No. 154705/1979), magnesium peroxyhydrate (Japanese Laid-Open Patent Publication No.
  • a detergent-dispersant composition for fuel or lubricating oils having the aforesaid excellent properties can be easily formed by a simplified operation of adding hydrotalcite to a hydrophobic dispersant such as an oil-soluble sulfonate dissolved in or mixed with a hydrophobic diluent such as a diluent oil and simply stirring the mixture, or if desired, performing the stirring after removing water from the mixture.
  • a hydrophobic dispersant such as an oil-soluble sulfonate dissolved in or mixed with a hydrophobic diluent such as a diluent oil
  • the active component of the composition of this invention advantageously reacts with undesirable acidic pollutant substances in lubricating or fuel oils much more rapidly than conventional overbasing agent such as magnesium carbonate, calcium carbonate, barium carbonate, magnesium hydroxide, a carbonic acid complex of magnesium or a magnesium peroxide, and exhibits a high level of affinity for these oils and the hydrophobic dispersant. Furthermore, it exhibits a good ability to disperse in these oils on its own without the aid of such a dispersant, and does not undergo flocculation, precipitation and separation.
  • the hydrotalcite component in accordance with this invention further shows an alkali value (AV) of at least 250 in these oils and can maintain a high-concentration stable ultrafine colloidal dispersion in these oils.
  • AV alkali value
  • hydrotalcite of formula (1) as an active component of a detergent-dispersant composition for lubricating or fuel oils are exhibited especially outstandingly in these oils when the hydrotalcite of formula (1) has a specific surface area, determined by the BET method, of not more than about 60 m 2 /g, preferably not more than about 40 m 2 /g, particularly not more than about 30 m 2 /g and an average secondary particle size of not more than about 5 micrometer particularly not more than about 1 micrometer.
  • the active ingredient of the composition of this invention is a hydrotalcite of the following formula wherein
  • m is not particularly limited, but for example, up to 7, preferably about 2 to 6.
  • x in the formula is preferably 4ZxZ8.
  • the crystal grains are fine particles having a size of less than about 0.1 micron, but on the other hand, its flocculating action becomes excessive, and even in an oil, forms secondary particles having an average size, of, for example, more than about 10 micrometers. This is likely to lead to precipitation even with the aid of a hydrophobic dispersant. Hence, such a specific surface area is not suitable in the present invention.
  • a hydrotalcite of formula (1) with or without surface-treatment with an anionic surface-active agent, which has a BET specific surface area of not more than about 60 m 2 /g, for example about 60 to about 10 m 2 /g, preferably not more than about 40 m 2 /g, especially not more than about 30 m 2 /g, and an average secondary particle size of not more than about 5 micrometers, for example about 5 to about 0.01 micrometer, preferably not more than about 1 micrometer.
  • the average secondary particle diameter in the present invention is a value measured by the following method.
  • a sample hydrotalcite is put on a glass plate, and the same amount of a dispersing medium ("Dislite", a trademark for a Vaseline-type dispersant made by Oken Shoji Sha) is added, followed by kneading.
  • the mixture is then diluted uniformly with a small amount of cyclohexanol.
  • One drop of the diluted mixture is put on a glass slide.
  • a cover glass is put on it and lightly pressed.
  • an image of the diluted mixture on a scale of 400 x is analyzed by using a Ruzex 401 particle counter.
  • the average secondary particle diameter of the sample is defined as that particle size which corresponds to a cumulative percentage of 50 in the normal distribution of the sample determined by using the analyzed value.
  • the hydrotalcite in accordance with this invention is coated at its surface with an anionic surface-active agent.
  • This surface-treatment serves to further increase the compatibility or dispersibility of the hydrotalcite with or in a dispersant and/or a lubricating or fuel oil and to form a more stable fine colloidal suspension in good yields.
  • it prevents the hydrotalcite from tending to form secondary particles, and in the event secondary particles are formed, the undesirable increase in the size of the secondary size is prevented.
  • anionic surfactant examples include alkali metal salts of higher fatty acids and alkali metal salts of hydrocarbon sulfonic acids.
  • specific examples of the surfactants include alkali metal salts of fatty acids having 10 to 30 carbon atoms such as sodium or potassium stearate, sodium or potassium oleate, sodium or potassium pal- mitate, sodium or potassium linolate and sodium or potassium linolenate; and alkali metal salts of hydrocarbon sulfonic acids having 10 to 30 carbon atoms such as sodium or potassium laurylbenzenesulfonate, sodium or potassium butylnaphthalenesulfonate and sodium or potassium dipropylnaphthalenesulfonate. These surfactants may be used singly or in combination with each other.
  • the surface treatment of the hydrotalcite with such an anionic surfactant can be effected, for example, by suspending a powder of the hydrotalcite of formula (1) in water, fully stirring the suspension, adding an aqueous solution of the anionic surfactant to the stirred suspension, and stirring the mixture fully for about 30 minutes to several hours, for example.
  • the temperature of the aqueous solution of the surfactant used is above a point at which the surfactant dissolves fully.
  • the surface treatment can be performed by adding a powder of the hydrotalcite to an aqueous solution of the anionic surfactant.
  • the treated product may, as required, be subjected to such an operation as dehydration, washing with water, dehydration, and drying.
  • the suitable amount of the anionic surfactant used in surface-treating the hydrotalcite is about 1 to about 10% by weight, preferably about 2 to about 6% by weight, based on the weight of the hydrotalcite.
  • the active ingredient of this invention can be used as a detergent-dispersant composition for lubricating or fuel oils in combination with a hydrophobic dispersant, a hydrophobic diluent and other additives which are well known in the art.
  • Such a hydrophobic (oil-soluble or oil-miscible) dispersant is, for example, a salt of a hydrophobic sulfonic acid.
  • Specific examples of such salts are those obtained by sulfonating alkylbenzenes having a molecular weight of about 300 to about 700. Both naturally occurring and synthetic alkylbenzenes are suitable for this purpose.
  • Many petroleum fractions within the range of lubricating oils contain alkylbenzene components which can be coverted to oil-soluble sulfonic acids by treatment with fuming sulfuric acid.
  • the terms "petroleum sulfonates” and “mahogany sulfonates” denote oil-soluble sulfonates of such natural derivatives.
  • Alkylbenzenes having a preferred molecular weight range can be synthesized by reacting benzene with chloro- paraffins or olefins using Friedel-Crafts catalysts such as aluminum chloride. Preferred alkylbenzenes may also be obtained as by-products of other chemical processes. For example, in the manufacture of household detergents, benzene is alkylated with a mixture of Clo-Clr, chloro- paraffins. The monoalkylbenzene (linear alkylate) as a main product is sulfonated and neutralized with sodium hydroxide to form a water-soluble detergent.
  • Distillation bottoms as by-products containing dialkylbenzenes, dialkyltetralins and diphenylalkanes are sulfonated and neutralized with, for example, magnesium oxide to form oil-soluble sulfonate dispersants.
  • sulfonic acid may occasionally be used instead of the sulfonate.
  • a hydrotalcite is added in an excessive amount sufficient to neutralize the sulfonate.
  • other sulfonate salts such as calcium sulfonate or barium sulfonate.
  • Other oil-soluble sulfonates such as dinonyl naphthalenesulfonates are also useful.
  • many other oil-soluble dispersants such as alkyl phenates and high-molecular-weight carboxylic acid salts, alkyl phosphonates and alkenyl succinimides are available. They may replace a part or the whole of the sulfonate in the present invention.
  • oil-soluble sulfonate salt in a pure condition, is normally a vitreous semi-solid, it is usually supplied and handled as a solution in a hydrophobic (oil-soluble or oil-miscible) diluent.
  • hydrophobic diluents which can be used in this invention include aliphatic or alicyclic hydrocarbons having 5 to 20 carbon atoms, including halogenated hydrocarbons, such as heptane, hexane, petroleum naphtha, isohexane, 2-methylhexane, n-octane, cyclohexane, 1,1-dimethylcyclohexane, and mineral spirits and chlorinated hydrocarbons (e.g., trichloroethane and tetrachloromethane); and aromatic hydrocarbons such having 6 to 20 carbon atoms such as benzene, toluene, o-xylene, m-xylene, p-xylene, mixed xylene, ethylbenzene and n-propylbenzene. If desired, these diluents may be used as a mixture of two or more.
  • the suitable amount of the hydrotalcite of formula (1) or its surface-treated product is such as to bring the alkali value of the resulting composition to at least 250. Since one gram of the hydrotalcite has an alkali value of as high as about 1500 to 1700, the hydrotalcite or its surface-treated product can be used in an amount of, for example, at least about 15%, preferably 17 to 50%, based on the weight of the detergent-dispersant composition.
  • Addition of the hydrotalcite or its surface treated product to the oil-soluble sulfonate can be effected by adding a suspension, a cake or a dry powder of the hydrotalcite to the oil-soluble sulfonate, and uniformly dispersing it by a homogenizer, a jet agitator, etc., if required, volatilizing water or another solvent, and further if required, removing the precipitate by filtration.
  • Example 2 The suspension of the hydrotalcite coated with sodium laurylbenzenesulfonate obtained in Example 1 was centrifuged, and the resulting cake was taken in an amount of 70g calculated as a dry product, and added to a diluted solution of oil-soluble magnesium alkylbenzenesulfonate having the same composition as in Example 1. The mixture was stirred for about 5 minutes by a jet agitator. The product was further distilled at about 150°C to remove water. The resulting product was used directly as a detergent-dispersant additive because it yielded no precipitate. This additive had an alkali value of 425.
  • a powder of a hydrotalcite of the formula Mg 4 Al 2 (OH) 13.2 (CO 3 ) 0.4 3H 2 0 having a BET specific surface area of 18 m 2 /g and an average secondary particle size of 0.16 pm was added to 20 liters of warm water kept at about 80°C, and the mixture was strongly stirred by a stirrer to disperse the hydrotalcite well. Then, 51 g of sodium oleate having a purity of 97% was added to about 1 liter of warm water kept at about 80°C to dissolve it completely. The solution was then added to the dispersion of the hydrotalcite, and the mixture was stirred fully for about 30 minutes. The product was centrifuged.
  • the resulting cake was added in an amount of 180g calculated as a dry product to a mixed solution consisting of 100g of oil-soluble magnesium sulfonate, 300g of hexane and 200g of toluene.
  • the mixture was stirred for about 5 minutes by a jet agitator.
  • the mixture was then filtered under reduced pressure, and the filtrate was distilled at about 150°C to remove toluene and water to obtain a detergent-dispersant additive.
  • the additive obtained had an alkali value of 465.
  • the ratio of recovery of the hydrotalcite in the product was about 67%.

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

Claims (7)

1. Detergens-Dispergierungs-Mischung für Schmier- oder Brennstofföle, dadurch gekennzeichnet, daß sie im wesentlichen aus
(a) einer als Detergens-Dispergierungsmittel wirksamen Menge eines Hydrotalcits mit einer spezifischen Oberfläche, bestimmt nach der BET-Methode, von bis zu etwa 60 m2/g und einer durchschnittlichen sekundären Teilchengröße von bis zu etwa 5 Ilm, wobei die Hydrotalcit-Teilchen unbehandelt oder mit einem anionischen oberflächenaktiven Mittel oberflächenbehandelt sind und wobei der Hydrotalcit durch die folgende Formel:
Figure imgb0004
angegeben wird, worin x eine ganze Zahl von 3<x<20 ist, y eine ganze Zahl von 0<y<2 ist und m eine ganze Zahl von bis zu 7 ist, und
(b) einem hydrophoben Dispergierungsmittel oder Verdünnungsmittel besteht.
2. Mischung nach Anspruch 1, dadurch gekennzeichnet, daß die durchschnittliche sekundäre Teilchengröße des Hydrotalcits bis zu etwa 1 pm beträgt.
3. Mischung nach Anspruch 1, dadurch gekennzeichnet, daß das anionische oberflächenaktive Mittel aus der Gruppe, bestehend aus Alkalimetallsalzen von höheren Fettsäuren und Alkalimetallsalzen von Kohlenwasserstoffsulfonsäuren, ausgewählt ist.
4. Mischung nach Anspruch 1, dadurch gekennzeichnet, daß das hydrophobe Dispergierungsmittel aus der Gruppe, bestehend aus Salzen von hydrophoben Sulfonsäuren, Alkylphenaten und hochmolekularen Carbonsäuresalzen, ausgewählt ist.
5. Mischung nach Anspruch 1, dadurch gekennzeichnet, daß die Menge des Hydrotalcits nicht weniger als 15 Gew.-%, bezogen auf das Gewicht der Mischung, beträgt.
6. Mischung nach Anspruch 1, dadurch gekennzeichnet, daß das hydrophobe Verdünnungsmittel aus der Gruppe, bestehend aus gegebenenfalls halogenierten aliphatischen oder alicyclischen Kohlenwasserstoffen und aromatischen Kohlenwasserstoffen, ausgewählt ist.
7. Mischung nach Anspruch 1, dadurch gekennzeichnet, daß die spezifische Oberfläche des Hydrotalcits bis zu etwa 40 m2g ist.
EP81103229A 1981-04-29 1981-04-29 Detergent-Dispersant-Zusammensetzung für Schmier- und Heizöle Expired EP0063631B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP81103229A EP0063631B1 (de) 1981-04-29 1981-04-29 Detergent-Dispersant-Zusammensetzung für Schmier- und Heizöle
DE8181103229T DE3172108D1 (en) 1981-04-29 1981-04-29 Detergent-dispersant composition for lubricating or fuel oils

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP81103229A EP0063631B1 (de) 1981-04-29 1981-04-29 Detergent-Dispersant-Zusammensetzung für Schmier- und Heizöle

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EP0063631A1 EP0063631A1 (de) 1982-11-03
EP0063631B1 true EP0063631B1 (de) 1985-09-04

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DE3819191A1 (de) * 1988-06-06 1989-12-07 Henkel Kgaa Verwendung von kationischen nichtsilikatischen schichtverbindungen in waschmitteln
DE3914916A1 (de) * 1989-05-06 1990-11-08 Henkel Kgaa Mittel zum viskositaetsaufbau in nichtwaessrigen fluessigphasen, verfahren zu ihrer herstellung und ihre verwendung
GB8927363D0 (en) * 1989-12-04 1990-01-31 Unilever Plc Detergent compositions
GB9026230D0 (en) * 1990-12-03 1991-01-16 Unilever Plc Detergent composition
WO1994003574A1 (en) * 1992-08-07 1994-02-17 Unilever N.V. Machine dishwashing and rinse aid compositions
DE4325237A1 (de) * 1993-07-28 1995-02-02 Basf Ag Verfahren zur Herstellung von Alkoxylierungsprodukten in Gegenwart von mit Additiven modifizierten Mischhydroxiden
BRPI1106099A2 (pt) 2011-03-18 2016-05-10 Toyota Motor Co Ltd agente aditivo, filtro de óleo e dispositivo lubrificante para máquina.
JP5542289B2 (ja) 2012-01-23 2014-07-09 トヨタ自動車株式会社 オイル添加物およびオイルフィルター
DE102012014473A1 (de) 2012-07-20 2014-01-23 Clariant International Ltd. Verfahren zur Absenkung des Schwefelwasserstoffgehalts von Mineralölen und Rückständen der Mineralöldestillation

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NL134312C (de) * 1967-06-23
US3713792A (en) * 1970-12-23 1973-01-30 Betz Laboratories Stabilization of fuel additives
GB1587866A (en) * 1976-11-22 1981-04-08 Nippon Oil Co Ltd Methyl tert-butyl ether
US4123231A (en) * 1977-02-04 1978-10-31 Petrolite Corporation Clear, bright oil-soluble aluminum-containing compositions
US4229309A (en) * 1977-07-18 1980-10-21 Petrolite Corporation Magnesium-containing dispersions

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EP0063631A1 (de) 1982-11-03

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