US3034907A - Anti-corrosive compositions - Google Patents

Anti-corrosive compositions Download PDF

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Publication number
US3034907A
US3034907A US746599A US74659958A US3034907A US 3034907 A US3034907 A US 3034907A US 746599 A US746599 A US 746599A US 74659958 A US74659958 A US 74659958A US 3034907 A US3034907 A US 3034907A
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Prior art keywords
parts
oil
sarcoside
corrosive
dihydroxyethyl
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US746599A
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English (en)
Inventor
Alois Kleemann
Rinaldo Roggero
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Novartis AG
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JR Geigy AG
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    • 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
    • C10M141/08—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 sulfur-, selenium- or tellurium-containing compound
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
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    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
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    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
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    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
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    • C10L1/14—Organic compounds
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    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
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    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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    • C10N2040/20—Metal working
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    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • compositions of matter which are effective agents for hindering or retarding rust formation on iron surfaces and ice formation in the exhaust system of internal combustion engines. It also concerns processes for the production of these agents as well as processes for the prevention or retardation of rust formation on iron surfaces and ice formation in the exhaust systems of internal combustion engines, and also the materials protected by the new compositions of matter.
  • compositions of matter made up from N-carboxyalkylamides of higher molecular carboxylic acids and certain hydroxyalkylated amines or nitrogen bases in oily carriers have a strong water-removing action on metal surfaces treated therewith and in particular, have a rust preventing or retarding action on iron surfaces which exceeds the sum of the actions to be expected from the individual components. Because of their strong water-displacing properties on metal surfaces, the compositions of matter are also effective agents against stalling due to carburettor icing in internal combustion engines under extreme climatic conditions.
  • compositions of matter which are characterized by a content of (a) a hydro phobic organic carrier, (b) a carboxylic acid amide monocarboxylic acid of the general Formula I Rr-C OIYT-R3C O OH R2 7 V (I) and (c) an at least equivalent amount of a hydroxyalkylated nitrogen base which contains at least one lipophilic radical.
  • R represents a lipophilic group or an organic radical containing at least one lipophilic group
  • R represents hydrogen or a lower alkyl group
  • R represents a lower alkylene group, in particular a methylene group.
  • the compounds of the general Formula I are functional derivatives of natural or synthetic amino acids and higher molecular carboxylic acids having lipophilic groups.
  • lipophilic groups are meant chiefly saturated and unsaturated, aliphatic or also alicyclic hydrocarbon radicals having straight or branched chains and 4 to 40 carbon atoms.
  • halogenated aliphatic radicals in particular alkyl radicals perfluorated in the end position can be used. If only one lipophilic hydrocarbon radical is present, then it has at least 8 and advantageously 12 to 18 carbon atoms. If more aliphatic and/ or alicyclic radicals are present, then together they have at least carbon atoms.
  • a single lipophilic radical should have at least 4 carbon atoms.
  • alkyl radicals perfluorated in the end position have a low number of carbon atoms, for example if they contain only 5 carbon atoms, they are already lipophilic.
  • Derivatives of aliphatic monocarboxylic acidshaving at least 10 carbon atoms are used advantageously according to the present invention as amide derivatives of the general Formula I. Examples are the derivatives of lauric, myristic, palmitic, stearic or higher fatty acids, then those of unsaturated higher carboxylic acids such as undecylenic acid, oleic acid and elaidic acid, ricinoleic acid, erucic and linoleic acid.
  • acid amide derivatives from mixtures of carboxylic acids such as are found in nature as esters of monovalent alcohols in waxes or as glycerides in fats and oils or which are contained in the so-called Fischer-Tropsch tail fraction acids can be used.
  • amide derivatives of those carboxylic acids can be used in which aliphatic hydrocarbon chains are interrupted by bridge-forming groups such as, for example, oxygen or sulphur ether groups or by aromatic radicals.
  • Examples are the derivatives of decyl-, dodecyl-, hexadecyl-, octadecyloxy acetic acids and thioacetic acids, also derivatives of a-heptyland )3- octyloxy propionic acids, of u-butoxylauric acid, of octyl and nonyl phenoxy acetic acids and phenyl stearic acid.
  • the amide derivatives of compounds of the general Formula I used according to the present invention are derived from aliphatic aminocarboxylic acids.
  • the compounds contain the radicals of low molecular amino acids such as, for example, those of glycin, alanine, valine and leucin and, in particular, those of the N-alkyl derivatives of these amino acids.
  • Compounds containing the radical of sarcosine such as, for example, oleyl sarcoside, are particularly effective in the compositions of matter according to the present invention'and are, therefore, preferred.
  • the acylamino fatty acids of the general Formula I are obtained from the low molecular amino fatty acids by reacting with fatty acid chlorides containing lipophilic radicals and, possibly, also aromatic radicals.
  • Hydroxyalkylated nitrogen bases which contain at least one lipophilic radical and at least one hydroxyalkyl group are used in the compositions of matter according to the present invention as amine component.
  • the lipophilic radical can be aliphatic, normal or branch chained, saturated or partly unsaturated or it can be alicyclic, sat urated or partly unsaturated.
  • a single lipophilic radical contains at least 10 carbon atoms and several lipophilic radicals together also contain at least 10 carbon atoms, an individual radical containing at least 4 carbon atoms.
  • the lipophilic radicals can be bound to the basic nitrogen atom either direct or by way of bridging members.
  • Divalent hydroxyalkyl, thioalkyl, aminoalkyl and, in particular, also carbonyl hydroxyalkyl groups are used as bridging members.
  • the cyclohexyl radical and homologues thereof, petroleum hydrocarbon radicals containing cyclopentyl radicals, the abietyl and dihydroabietyl radical are examples of alicyclic lipophilic radicals.
  • straight chained alkyl groups with more than 10 carbon atoms form the lipophilic radical of the nitrogen bases used according to the present invention, for example the lauryl, cetyl, oleyl or stearyl radical.
  • the hydroxyalkyl group of the nitrogen base is advantageously low molecular and contains 2 to 6 carbon atoms and 1-3 hydroxyl groups. 7 Examples are the Z-hydroxyethyl, Z-hydroxypropy-l, 2,3-dihydroxypropyl and the trihydroxy-tert. butyl groups. A great num: ber of hydrophilic groups should not be present however. lntrihydroxy-tert. butylamine bases, therefore, advantageously at least one hydroxy group is esterified with a higher fatty acid or an alkoxy fatty acid.
  • reaction products from primary and secondary aliphatic monoand poly-amines containing lipophilic radicals and aliphatic or araliphatic epoxides such as propylene oxide, styrene oxide and, in particular, ethylene oxide, are preferred.
  • Examples are stearyl-diethanolamine, oleyl diethanolamine, N hydroxyethyl N stearyl-ethylene diamine, N'-hydroxyethyl-N-oleyl-ethylene diamine, N"- hydroxyethyl-N-stearyl-diethylene triamine, N"-hydroxyethyl N oleyl-diethylene triamine, N.N.N-trihydroxyethyl-N-stearyl-ethylene diamine.
  • other amines as defined such as, for example, triethanolamine dilauric acid ester, dimethyl-trihydroxy-tert.
  • Carboxylic acid amide-monocarboxylic acids of the general Formula I and hydroxyalkylated amines having a lipophilic radical can be used in various proportions in the compositions of matter according to the present invention. In general, almost equimolecular or stoichiometric amounts are used. Sometimes so much hydroxyalkylated amines are used that complete salt formation with the carboxylic acid amide monocarboxylic acid occurs and an excess serves as solvent.
  • the carboxylic acids are used as such, but they can also be used in the form of their metal salts or salts of organic bases, both of which are soluble in oil.
  • compositions of matter according to the present invention contain hydrophobic organic compounds as carriers for the water displacing and rust preventing active substances, ie those substances which are insoluble in Water.
  • Such hydrophobic carriers are the natural and synthetic, solid and liquid and, of these, chiefly the saturated hydrocarbons, and also waxes, fats and oils as well as resins, lacquers, varnishes.
  • the choice of carrier as well as the content of active ingredient is determined by the intended use.
  • the content of active substances depends also possibly on their solubilities in the carriers chosen.
  • the content of active substances in the compositions of matter can vary within wide margins.
  • sufiicient as anti-corrosive agent for example as low as 0.001, but generally 0.1 to 5% calculated on the weight of the hydrophobic carrier and, to prevent icing in the exhaust system of internal combustion engines for example to 200 parts per million parts of power fuel.
  • F or the protection of iron surfaces against rust for example mineral or synthetic lubricating oils, lubricating greases, hydraulic oils, compressor oils, turbine oils, soluble oils, grinding oils and cutting oils can be used as hydrophobic carriers in the compositions of matter according to the present invention.
  • the oily carriers mentioned above can be combined with more easily volatile diluents and with propellants.
  • the anti-corrosive agents according to the present invention can be used for the protection of clean iron parts of storage vessels, pipes, turbines, motors, firearms and other machines or parts thereof.
  • the anti-corrosive agents according to the present invention are also very well suited for the temporary protection of iron stored in a half finished state.
  • the new anti-corrosive agents can be mixed, for example with linseed oil colours, synthetic resin emulsions, lacquers, silicone oils and under coatings.
  • the temporary protection of the surfaces of iron materials they are used for example in petroleum or fats and, in particular, in mineral oils.
  • the active substances used in the compositions of matter according to the present invention generally have no injurious eifect on the hydrophobic carriers. In the same way, when used in lubricating oils, paints, combustion oils etc., they have practically no injurious eifect on the properties of these agents. They are also compatible with the usual oil additives such as antioxidants, metal deactivators, anti-frothing agents, surface active agents, dispersion promoters, viscosity improvers or dyestufis and can be used therefore with such additives. Some of the new compositions of matter according to the present invention are valuable anti-corrosive agents on metals other than lI'OIl.
  • compositions of matter according to the present invention are suitable for the rust protective treatment of the under side of motor vehicles or for the drying and temporary storage of iron tools which, when being worked upon, have been cooled with water.
  • the compositions of matter according to the present invention are suitable for the rust protective treatment of the under side of motor vehicles or for the drying and temporary storage of iron tools which, when being worked upon, have been cooled with water.
  • To this same property is due their activity against icing of carburettors in internal combustion engines which often occurs under damp or cold atmospheric conditions when using volatile fuel following a period of light load operation. The icing causes blocking of the throttle valve and the engine stalls. Very slight additions of for example 20 to 200 parts per million of the components (b) and (c) to volatile fuels (50% ASTM [American Society for Testing Materials] distillation point for example less than C.) hinders the icing.
  • ASTM American Society for Testing Materials
  • Anti-corrosive agents according to the present invention therefore consist of an oily carrier, for example a synthetic and, advantageously, a mineral lubricating oil or a lubricating grease, and 0.1 to 5% calculated on the weight of the oily carrier of a composition of matter consisting of an acylamino fatty acid of the general Formula I
  • R is a lipophilic radical from the classes of aliphatic hydrocarbon radicals with 12 to 30 carbon atoms, of alkoxy methylene radicals and alkyl thiomethylene radicals with 12 to 30 carbon atoms, and of alkyl phenoxy methylene radicals with alkyl substituents totalling at least 8 carbon atoms, the first class being preferred because of easier technical accessibility and good influence on the activity of the composition of matter; wherein R is hydrogen, or a low molecular alkyl group and R is a lower alkylene group, preferably the methylene group; and of at least the equivalent amount of a hydroxyalkylated nitrogen base which contains one or
  • X represents a bridging member which is bound to the nitrogen atom by means of an aliphatic carbon atom and which is selected from the group of lower-0- alkylene, -S-alkylene-, -O-hydroxyalkylene, -S-hydroxyalkylene,
  • n. represents the integer or 1
  • R represents hydrogen, a lower alkyl or lower hydroxyalkyl or lower aminoalkyl radical
  • R is the same as (LX and R the condition being that of the radicals X, R and R at least one is a low molecular, hydroxyalkylated aliphatic radical.
  • L represents an aliphatic hydrocarbon radical with 12 to 18 carbon atoms
  • n is 0 and at least one of R and R is a low molecular hydroxyalkyl or hydroxyalkylarninoethyl radical.
  • the fuel mixtures according to the present invention contain as predoninant part a hydrocarbon mixture of benzene of 50% ASTM distillation point under 115 and 10 to 200 parts per million, advantageously 20 to 100 parts per million of an antistalling adjuvant consisting of an acylamino fatty acid of the general Formula I with the same definition of the substituents as is given in the preceding paragraph for the anti-corrosive agent and of at least an equivalent amount of a hydroxyalkylated nitrogen base with a lipohilic radical as defined in the preceding paragraph.
  • the lipophilic radical is an alkyl or alkenyl radical containing 12 to 18 carbon atoms
  • the hydroxyalkyl group is advantageously a 2-hydroxyethyl group
  • the nitrogen base is advantageously an aliphatic monoor poly-amine, in the latter case, advantageously an ethylene -arnine where n is l to 3 and advantageously 1.
  • the fuel mixtures according to the present invention can contain other usual additives.
  • Example 1 20 parts of oleoyl sarcoside and of N-(hydroxyethylamiuoethyl)-stearylamine of the formula are dissolved in 750 parts of spindle oil of 1-2 Engler degrees (50 measured). parts of fenchyl alcohol, to improve the smell, 20 parts of micro'ceresin, to modify the oil film, as well as 20 parts of morpholine and 165 parts of distilled petroleum, as solvent, are added to the mixture. A thinly liquid anti-corrosive oil which can be painted well is obtained.
  • Example 2 25 parts of stearoyl sarcoside and 25 parts of N-bis- (hydroxyethyl)-stearylamine are rubbed with 5 parts of terpin into a homogeneous mass. The thickly. liquid mixture is then dissolved at room temperature in 945 parts of mineral oil SAE 40 (-12 Engler degrees at 50).
  • composition of matter is suitable for example for the treatment of weapons, tools, machines or power-propelled vehicles to prevent the iron parts thereof from the formation of rust or at least to strongly hinder such formation.
  • Example 3 A mixture of 25 parts of oleoyl sarcoside and 25 parts of N-bis-(hydroxyethyl)-stearylamine is dissolved at room temperature in 760 parts of spindle oil of a viscosity of 1-2' Engler degrees (measured at 50"). 5. partsof fenchyl alcohol, 20 parts of ceresin, (20 parts of dioxan and '145 parts ofdistilled petroleum are added to the solution. An excellent anti-corrosive oil is obtained which can be sprayed Well both from an ordinary spray and from an atomiser. When used as a grease, the film adheres well to the metal surface. Lacquers, synthetic materials and rubber are not noticeably; affectedby the oil.
  • Series B are coated with a mixture which contains 5% by weight of N-(dihydroxyethyl)-stearylamine instead of oleoyl .sarcoside, and series A is coated with'an oil mixture not containing an anti-corrosive agent.
  • the results are as follows: 1
  • Series A shows clear rust formation after 10 hours exposure to fog spray
  • Series B shows clear rust posure to fog spray
  • Series C shows clear rust formation after 11-0 hours exposure to fog spray
  • Series D showed no rust formation after more than 500 hours exposure.
  • N.N.N'-tris-( hydroxyethyl)-aminoethyl- 'stearylamine of the formula:
  • Example 6 2 parts of oleyl sarcoside, 2.4 parts of dimethylarninotrimethylolmethane oleic acid monoester and 3 parts of microcrystalline wax are dissolved while warming in a mixture of 4 parts of dioxane and 90 parts of diesel fuel oil. A relatively thinly liquid anti-corrosive oil which can be sprayed and painted is obtained.
  • iron plates which have been brushed completely clean (steel with 0.08% C) are dipped in this oil and are hung up for one day to allow excess oil to run off.
  • Example 7 2 parts of dimethylaminotrimethylolmethane oleic acid diester, 1 part of stearoyl sarcoside, 2 parts of microceresin, 2 parts of dioxan and 0.5 part of fenchyl alcohol are dissolved while warming to about 50 in 92 parts of mineral oil of 10-12 Engler degrees (measured at 50). An opalescent anti-corrosive oil is obtained.
  • Iron sheets brushed clean are painted with this anticorrosive oil and their stability to corrosion is tested by storing them in a corrosion chamber.
  • the mist in the Example 8 3 parts of triethanolamine dilauric acid ester, 2 parts of oleyl sarcoside, 5 parts of fenchyl alcohol, 20 parts of ceresin, 50 parts of palm nut oil and 20 parts of mineral oil are melted into a homogenous mass while stirring at about After cooling, a soft anti-corrosive grease which can be smeared on is obtained. It can be used, for example for instruments or firearms.
  • Example 9 2 parts of dihydroxyethyl oleylamine decylthioacetic acid monoester, 1 part of oleyl sarcoside and 2 parts of dioxan are dissolved in parts of a mineral oil of a viscosity of Saybolt Universal seconds (38) refined by extraction. An anti-corrosive oil which can easily be sprayed or smeared is obtained. If steel sheets (0.08% C) are brushed clean and sprayed with this anti-corrosive oil and then kept in an atmosphere saturated with steam, after 30 days they are completely shining and free from all traces of rust whilst control sheets which have only been sprayed with the mineral oil mentioned without additives, are covered with a layer of rust after this time under the same conditions.
  • Example 10 2 parts of dihydroxyethylstearylamine lauroyl sarcosine monoester, 1 part of oleyl sarcoside, 2 parts of dioxan and 0.5 part of fenchyl alcohol and 2 parts of microceresin are dissolved in 92.5 parts of a petroleum distillate (boiling range 150-210, flash point over 35). If pieces of iron which, while being worked upon are cooled by spraying with water, are dipped into the composition of matter described above immediately afterwards then the water is removed from the surface of the metal within a few seconds. On being stored in a damp, corrosive atmosphere, pieces of iron dried in the manner described are remarkably stable to rust.
  • a petroleum distillate boiling range 150-210, flash point over 35
  • the dihydroxyethylstearylamine lauroyl sarcosine monoester is replaced by the same amount of dihydroxyethyl oleylamine oleyl sarcosine monoester then a water removing anti-corrosive preparation having similar activity is obtained.
  • Example 11 Six fuel mixtures are prepared as follows: equal parts of first oleoyl sarcoside and then octadecyl diethanolamine are dissolved in a fuel for internal combustion engines containing petroleum distillates and reformed hydrocarbons, the 50% ASTM distillation point of which fuel is 90. The six fuels are made up in the ratio of 0, 10, 20, 30, 40 and 50 parts of additives to one million parts of fuel. The anti-icing action was tested as follows:
  • a 1 cylinder motor with a Solex carburettor was run with the fuels prepared in laboratory tests under the following test conditions and the time was measured in minutes until the motor stalled due to blocking of the carburettor.
  • An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties, said composition consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of an acylamino fatty acid selected from the group consisting of oleoyl sarcoside and stearoyl sarcoside, and of a hydroxy alkylated nitrogen base selected from the group consisting of stearyl diethanolamine, dihydroxyethyl oleylamine decylthioacetic acid monoester, dihydroxyethyl stearylamine lauroyl sarcosine monoester, dimethylaminotrihydroxy methyl methane oleic acid monoester, N.N'.N-trihydroxyethyl-N-stearyl-ethylene diamine and dihydroxyethyl oleylamine oleyl sat-cosine monester
  • An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties, said composition consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of oleoyl sarcoside and of stearyl diethanolamine, the ratio of parts by weight of said oleoyl sarcosi-de to stearyl diethanolamine in said mixture being substantially between 0.5:1 to 15:1.
  • An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties, said composition consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of stearoyl sarcoside and of stearyl diethanolamine, the ratio of parts by weight of said stearoyl sarcoside to stearyl diethanolamine in said mixture being substantially between 0.5:1 to 1.5 :1.
  • An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of oleoyl sarcoside and o f dihydroxyethyl oleylamine decylthioacetic acid monoester, the rationof parts by weight of said oleoyl sarcoside to dihydroxyethyl oleylamine decylthioacetic acid monoester in said mixture being substantially between 0.5 :1 to 1.5 :1.
  • An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties, said composition consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of oleoyl sarcoside and of dihydroxyethyl stearylamine lauroyl sarcosine monoester, the ratio of parts by weight of said oleoyl sarcoside to dihydroxyethyl stearylamine lauroyl sarcosine monoester in said mixture being substantially between 0.5:1 to 1.5 :1.

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Cited By (22)

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US3259577A (en) * 1963-02-19 1966-07-05 Socony Mobil Oil Co Inc Lubricant and additives therefor
US3305406A (en) * 1964-04-06 1967-02-21 Western Electric Co Method of fluxing an article to be soldered with noncorrosive fluxing compositions
US3337472A (en) * 1966-04-08 1967-08-22 Union Oil Co Composition for inhibiting corrosion
US3469955A (en) * 1965-06-08 1969-09-30 Shell Oil Co Corrosion-inhibited hydrocarbon compositions
JPS5091546A (de) * 1973-12-17 1975-07-22
US3977994A (en) * 1974-06-24 1976-08-31 Universal Oil Products Company Rust inhibiting composition
EP0351964A1 (de) 1988-06-24 1990-01-24 Exxon Chemical Patents Inc. Synergische Additivzusammensetzung, verwendbar in Kraftübertragungszusammensetzungen
US5089226A (en) * 1986-01-20 1992-02-18 Nippon Mining Co., Ltd. Method for protecting austenitic stainless steel-made equipment from occurrence of stress-corrosion cracking
US5178786A (en) * 1989-08-04 1993-01-12 The Lubrizol Corporation Corrosion-inhibiting compositions and functional fluids containing same
US5185090A (en) * 1988-06-24 1993-02-09 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing same
US5242612A (en) * 1988-06-24 1993-09-07 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions
US5314633A (en) * 1988-06-24 1994-05-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions and process for preparing same
US5320768A (en) * 1988-06-24 1994-06-14 Exxon Chemical Patents Inc. Hydroxy ether amine friction modifier for use in power transmission fluids and anti-wear additives for use in combination therewith
US5326487A (en) * 1988-06-24 1994-07-05 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions
US5534170A (en) * 1988-06-24 1996-07-09 Exxon Chemical Patents Inc. Mixed phosphorus- and sulfur-containing reaction products useful in power transmitting compositions
US5948237A (en) * 1996-10-15 1999-09-07 Clariant Gmbh Use of sarcosinates as asphaltene-dispersing agents
EP1092788A3 (de) * 1999-10-14 2001-10-04 Brad-Chem Technology Ltd. Korrosionsinhibitierende Zusammensetzungen
EP1359206A1 (de) * 2002-04-23 2003-11-05 Rohm And Haas Company Addukte aus Aminen und ungesättigten Säuren als Asphalten-Dispergiermittel in Rohöl
US20040232043A1 (en) * 2003-05-23 2004-11-25 Ravindranath Mukkamala Amine-unsaturated acid adducts as asphaltene dispersants in crude oil
US20080139420A1 (en) * 2005-01-21 2008-06-12 Hiroshi Takiuchi Rust Preventive Package Containing Bearing for Machine Tool and Rust Preventive Packaging Method
US10550304B2 (en) 2013-08-01 2020-02-04 M-I Drilling Fluids Uk Limited Quaternary ammonium compounds and gas hydrate inhibitor compositions
CN110914389A (zh) * 2018-01-31 2020-03-24 出光兴产株式会社 润滑脂组合物

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DE3035326A1 (de) * 1980-09-19 1982-05-06 Hoechst Ag, 6000 Frankfurt Korrosions- und kavitationshemmende kuehlfluessigkeit
DE3047304A1 (de) * 1980-12-16 1982-07-29 Basf Ag, 6700 Ludwigshafen Verwendung von polyhydroxy-polyalkylen-polyamin-salzen von maleinamidsaeuren als korrosionsschutzmittel in wasser-in-oel-emulsionen

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US2790779A (en) * 1953-07-27 1957-04-30 Geigy Chem Corp Rust preventive compositions containing monoamidocarboxylic acids
US2843464A (en) * 1956-04-06 1958-07-15 Gulf Research Development Co Non-stalling gasoline fuel compositions
US2856363A (en) * 1955-12-01 1958-10-14 Pure Oil Co Stable anti-rust lubricating oil
US2872303A (en) * 1955-05-18 1959-02-03 Exxon Research Engineering Co Anti-stalling gasoline agent
US2902354A (en) * 1956-06-29 1959-09-01 Socony Mobil Oil Co Inc Anti-stall gasoline
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US2403067A (en) * 1943-09-08 1946-07-02 Union Oil Co Anticorrosion composition
US2706677A (en) * 1950-06-28 1955-04-19 Exxon Research Engineering Co Amines and amides as anti-stalling additives
US2790779A (en) * 1953-07-27 1957-04-30 Geigy Chem Corp Rust preventive compositions containing monoamidocarboxylic acids
US2872303A (en) * 1955-05-18 1959-02-03 Exxon Research Engineering Co Anti-stalling gasoline agent
US2856363A (en) * 1955-12-01 1958-10-14 Pure Oil Co Stable anti-rust lubricating oil
US2843464A (en) * 1956-04-06 1958-07-15 Gulf Research Development Co Non-stalling gasoline fuel compositions
US2902354A (en) * 1956-06-29 1959-09-01 Socony Mobil Oil Co Inc Anti-stall gasoline
US2919979A (en) * 1957-06-11 1960-01-05 American Oil Co Rust inhibitor for gasoline

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3259577A (en) * 1963-02-19 1966-07-05 Socony Mobil Oil Co Inc Lubricant and additives therefor
US3305406A (en) * 1964-04-06 1967-02-21 Western Electric Co Method of fluxing an article to be soldered with noncorrosive fluxing compositions
US3469955A (en) * 1965-06-08 1969-09-30 Shell Oil Co Corrosion-inhibited hydrocarbon compositions
US3337472A (en) * 1966-04-08 1967-08-22 Union Oil Co Composition for inhibiting corrosion
JPS5091546A (de) * 1973-12-17 1975-07-22
US3977994A (en) * 1974-06-24 1976-08-31 Universal Oil Products Company Rust inhibiting composition
US5089226A (en) * 1986-01-20 1992-02-18 Nippon Mining Co., Ltd. Method for protecting austenitic stainless steel-made equipment from occurrence of stress-corrosion cracking
US5326487A (en) * 1988-06-24 1994-07-05 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions
US5078893A (en) * 1988-06-24 1992-01-07 Exxon Chemical Patents Inc. Synergistic combination of additives useful in power transmitting compositions
US5185090A (en) * 1988-06-24 1993-02-09 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing same
US5242612A (en) * 1988-06-24 1993-09-07 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions
US5314633A (en) * 1988-06-24 1994-05-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions and process for preparing same
US5320768A (en) * 1988-06-24 1994-06-14 Exxon Chemical Patents Inc. Hydroxy ether amine friction modifier for use in power transmission fluids and anti-wear additives for use in combination therewith
EP0351964A1 (de) 1988-06-24 1990-01-24 Exxon Chemical Patents Inc. Synergische Additivzusammensetzung, verwendbar in Kraftübertragungszusammensetzungen
US5534170A (en) * 1988-06-24 1996-07-09 Exxon Chemical Patents Inc. Mixed phosphorus- and sulfur-containing reaction products useful in power transmitting compositions
US5178786A (en) * 1989-08-04 1993-01-12 The Lubrizol Corporation Corrosion-inhibiting compositions and functional fluids containing same
EP0611818A1 (de) 1990-07-31 1994-08-24 Exxon Chemical Patents Inc. Gemischte, Phosphor und Schwefel enthaltende Reaktionsprodukte hergestellt unter niedrigen Druck, verwendbar in Kraftübertragungszusammensetzungen und Verfahren zu deren Herstellung
US5948237A (en) * 1996-10-15 1999-09-07 Clariant Gmbh Use of sarcosinates as asphaltene-dispersing agents
EP1092788A3 (de) * 1999-10-14 2001-10-04 Brad-Chem Technology Ltd. Korrosionsinhibitierende Zusammensetzungen
US6984340B1 (en) 1999-10-14 2006-01-10 Brad-Chem Technology Limtied Corrosion inhibiting formulations
EP1359206A1 (de) * 2002-04-23 2003-11-05 Rohm And Haas Company Addukte aus Aminen und ungesättigten Säuren als Asphalten-Dispergiermittel in Rohöl
US20040232043A1 (en) * 2003-05-23 2004-11-25 Ravindranath Mukkamala Amine-unsaturated acid adducts as asphaltene dispersants in crude oil
US20080139420A1 (en) * 2005-01-21 2008-06-12 Hiroshi Takiuchi Rust Preventive Package Containing Bearing for Machine Tool and Rust Preventive Packaging Method
US7819246B2 (en) * 2005-01-21 2010-10-26 Ntn Corporation Rust preventive package containing bearing for machine tool and and rust preventive packaging method
US10550304B2 (en) 2013-08-01 2020-02-04 M-I Drilling Fluids Uk Limited Quaternary ammonium compounds and gas hydrate inhibitor compositions
CN110914389A (zh) * 2018-01-31 2020-03-24 出光兴产株式会社 润滑脂组合物
US20200148970A1 (en) * 2018-01-31 2020-05-14 Idemitsu Kosan Co., Ltd. Grease composition
US11254892B2 (en) * 2018-01-31 2022-02-22 Idemitsu Kosan Co., Ltd. Grease composition

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GB868990A (en) 1961-05-25
DE1271287B (de) 1968-06-27
NL109353C (nl) 1964-09-15
CH357130A (de) 1961-09-30
BE569325A (fr) 1961-04-21
FR1214872A (fr) 1960-04-12

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