GB684640A - Reaction products of n-acylated polyalkylenepolyamines with alkenyl succinic acids or anhydrides or derivatives thereof - Google Patents

Reaction products of n-acylated polyalkylenepolyamines with alkenyl succinic acids or anhydrides or derivatives thereof

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Publication number
GB684640A
GB684640A GB20271/50A GB2027150A GB684640A GB 684640 A GB684640 A GB 684640A GB 20271/50 A GB20271/50 A GB 20271/50A GB 2027150 A GB2027150 A GB 2027150A GB 684640 A GB684640 A GB 684640A
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Prior art keywords
anhydrides
acid
acids
anhydride
moles
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GB20271/50A
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ExxonMobil Oil Corp
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Socony Vacuum Oil Co Inc
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Publication of GB684640A publication Critical patent/GB684640A/en
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38Heterocyclic nitrogen compounds
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/16Radicals substituted by nitrogen atoms
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    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16Amides; Imides
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    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23FNON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10Inhibiting 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
    • C23F11/14Nitrogen-containing compounds
    • C23F11/149Heterocyclic compounds containing nitrogen as hetero atom
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • C10M2207/404Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
    • C10M2215/065Phenyl-Naphthyl amines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/223Five-membered rings containing nitrogen and carbon only
    • C10M2215/224Imidazoles
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226Morpholines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26Amines
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    • C10M2215/30Heterocyclic compounds
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/06Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/08Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/135Steam engines or turbines
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/22Metal working with essential removal of material, e.g. cutting, grinding or drilling
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    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Semi-solids; greasy

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

Abstract

Corrosion inhibiting compounds are manufactured by reacting one mole. of a polyalkylenepolyamine, containing x nitrogen atoms and x-1 alkylene groups per molecule, with from one to x-1 moles of a monocarboxylic acid or its anhydride or halide or a mixture of said compounds, and reacting the intermediate product with from one to x-1 moles of an alkenyl succinic acid anhydride or the corresponding acid or a compound obtained from either by saturation of the double bond by an addition reaction (e.g. with hydrogen, sulphur, bromine, chlorine or iodine), the sum of the number of moles. of the monocarboxylic acid or equivalent and of the alkenyl succinic acid anhydride or equivalent being not greater than x. When the terminal nitrogen atom of the polyalkylenepolyamine is separated from the next nitrogen atom by two or three carbon atoms, the first molecule of monocarboxylic acid appears to react at both these points to form an imidazoline or D 2-tetrahydropyrimidine ring (e.g. one mole of caprylic acid with one mole of diethylene- or dipropylene-triamine yields respectively 1-b -aminoethyl - 2 - n - heptylimidazoline and 1 - g - aminopropyl - 2 - n - heptyl - D 2 - tetrahydropyrimidine), and in these cases some or all of the alkenyl succinic acid anhydride will be present merely in physical admixture unless the number of moles of monocarboxylic acid is not more than x-2 and the sum of the number of moles of monocarboxylic acid and of alkenyl succinic acid anhydride is not more than x-1. The first stage of the reaction is preferably effected at 130-160 DEG C., advantageously with removal of water liberated by azeotropic distillation with a hydrocarbon solvent (preferably aromatic), and the second stage preferably below 110 DEG C., advantageously in the presence of a solvent, especially one which forms an azeotropic mixture with water, or a mineral oil. Preferably the polyalkylenepolyamine is a polyethylenepolyamine containing 2-6 ethylene groups per molecule, the monocarboxylic acid is aliphatic (especially with a chain length of 10-30 carbon atoms), and the alkenyl succinic acid anhydride contains 8-18 carbon atoms in the alkenyl radical. Specified reactants, some of which are employed in examples, are: polyalkylene polyamines (obtainable by the action of ammonia on alkylene or substituted alkylene dihalides, especially ethylene bromide): diethylene-, di-(methylethylene)-, di-(1-methylbutylene)-, di-(1 - methylamylene) -, di - (1 - methyl - 4 - ethylbutylene)-, didodecylene-, dieicosylene-, di-(1 : 2 - dimethyl - 14 - nonyltetradecylene)- and di - (1 : 18 - dioctyloctadecylene) - triamine, triethylene-, tri-(ethylethylene)-, tri-(1 : 2 : 2-trimethylethylene)-, tri-(1 : 4-diethylbutylene)-, tridecylene-, tri-(1 : 15-dimethylpentadecylene)-, trioctadecylene- and tri-(1-methyl-1-phenyl-3-propylpropylene) - tetramine, tetraethylene-, tetrabutylene-, tetra-(1 : 3-dimethylpropylene)-, tetraoctylene-, tetra-(1 : 4-dipropylbutylene)-, tetratetradecylene-, tetra-(1 - methyl - 3 - benzylpropylene) - and tetra - (1 - ethyl - 2 - benzylethylene) - pentamine, penta - (1 - methylpropylene) -, penta-amylene -, penta - (1 : 5 - dimethylamylene)-, penta - (1 : 2 - dimethyl - 1 - isopropylethylene) -, penta - (1 - methyl - 4 - nonylbutylene)- and penta-(1-methyl-2-benzylethylene)-hexamine, hexapropylene- and hexa(1 : 1-dimethylethylene)-heptamine; monocarboxylic acids and equivalents; formic, acetic, fluoroacetic, bromacetic, propionic, b -chloropropionic, propiolic, isobutyric, a -bromobutyric, isocrotonic, b -ethylacrylic, valeric, a -bromoiso-valeric, allylacetic, hexanoic, sorbic and b , chloroacrylic acid, acetic, propionic, butyric, crotonic, acrylic and caproic anhydride, acetyl chloride and fluoride, propionyl bromide, crotonic acid chloride, hexanoyl chloride, nitrosobutyric acids, aminovaleric acids, aminohexanoic acids, heptanoic, octanoic, 2-ethylhexanoic, a -bromo-octanoic, decanoic, dodecanoic, undecylenic and tetradecanoic acid, heptanoic anhydride, myristoyl bromide, hexadecanoic, palmitic, oleic, heptadecanoic, stearic, linoleic and linolenic acid, phenylstearic acids, xylylstearic acids, a -dodecyltetradecanoic, arachidic, behenic, behenolic, erucic, cerutic, selacholeic, montanic, melissic and ketotriacontic acid, erucic and heptacosanoic anhydride, hexahydrobenzoic acid, hexahydrobenzoyl bromide, furoic acid, chlorofuroic acids, thiophenecarboxylic acids, picolinic, nicotinic and benzoic acid, benzoic anhydride, benzoyl chloride and iodide, toluic acids and anhydrides, xylic acids, chloranthranilic acids, chlorodinitrobenzoic acids, cinnamic acid and anhydride, aminocinnamic acids, salicylic acid, hydroxytoluic acids, iodosalicylic acids, naphthoyl chlorides and naphthoic acids, and mixtures of oleic acid with decanoic or dodecanoic acid; alkenylsuccinic acid anhydrides and equivalents: ethenylsuccinic acid and anhydride, ethylsuccinic anhydride, propenylsuccinic anhydrides and their sulphurized derivatives, butenylsuccinic acids, 2-methylbutenylsuccinic anhydrides, 1 : 2-dichloropentylsuccinic anhydride, hexenylsuccinic anhydrides, hexylsuccinic acid, sulphurized 3 - methylpentenylsuccinic anhydrides, 2 : 3- and 3 : 3-dimethylbutenylsuccinic anhydrides, 1 : 2 - dibromo - 2 - ethylbutylsuccinic acid, heptenylsuccinic anhydrides, 1 : 2 - di-iodo-octylsuccinic acid, octenylsuccinic anhydrides, 2 - methylheptenylsuccinic anhydrides, 4 - ethylhexenylsuccinic acids, 2 - isopropylpentenylsuccinic anhydrides, nonenylsuccinic anhydrides, 2-propylhexenylsuccinic anhydrides, decenylsuccinic acids, and anhydrides, 5 - methyl - 2 - isopropylhexenylsuccinic anhydrides, 1 : 2 - dibromo - 2 - ethyloctenylsuccinic anhydrides, decylsuccinic anhydride, undecenylsuccinic anhydrides, 1 : 2-dichloroundecylsuccinic acid, 3 - ethyl - 2 - tert. - butylpentenylsuccinic anhydrides, dodecenylsuccinic acids and anhydrides, 2-propylnonenylsuccinic anhydrides, 3-butyloctenyl - succinic anhydrides, tridecenylsuccinic anhydrides, tetradecenylsuccinic anhydrides, hexadecenylsuccinic anhydrides, sulphurized octadecenylsuccinic acids, octadecylsuccinic anhydride, 1 : 2 - dibromo - 2 - methylpentadecylsuccinic anhydrides, 8-propylpentadecylsuccinic anhydride, eicosenylsuccinic anhydrides, 1 : 2-dichloro - 2 - methylnonodecenylsuccinic anhydrides, 2-octyldodecenylsuccinic acids, 1 : 2-diiodotetracosenylsuccinic anhydrides, hexacosenylsuccinic acids and anhydrides, hentriacontenylsuccinic anhydrides, triisobutenylsuccinic anhydride, and commercial mixtures of alkenylsuccinic anhydrides containing 6-8, 8-10 or 10-12 carbon atoms in the alkenyl groups.ALSO:Oils, fats and waxes.-Corrosion inhibitors, suitable for addition to mineral lubricating oils, light petroleum products such as fuel oils, petroleum waxes such as slack wax and paraffin wax, natural waxes such as carnauba wax, Japan wax and beeswax, natural fats and oils such as sperm oil, tallow, cottonseed oil, castor oil, linseed oil, tung oil, soya bean oil, oiticica oil and oleo oil, and greases, consist of reaction products of one mole of a polyalkylene-polyamine, containing x nitrogen atoms and x-1 alkylene groups per molecule, with from one to x-1 moles of a monocarboxylic acid or its anhydride or halide or a mixture of said compounds, and with from one to x-1 moles of an alkenyl succinic acid anhydride or the corresponding acid or a compound obtained from either by saturation of the double bond by an addition reaction, the sum of the number of moles of the monocarboxylic acid or equivalent and of the alkenyl succinic acid anhydric or equivalent being not greater than x. In some cases the preparation of the corrosion inhibitors, or especially the second stage thereof, is advantageously carried out in solution or dispersion in a mineral oil. In an example, the reaction product of 1.5 moles of triethylenetetramine with 2 moles of oleic acid is heated with 3.4 moles of triisobutenyl succinic acid anhydride in a furfural-refined Midcontinent (Rodessa) distillate mineral lubricating oil; the product may be added to a leaded, catalytically cracked gasoline. Tables show the rust inhibiting properties of this and other products in the said oil and in a blend of solvent refined Midcontinent residual stock and solvent refined Midcontinent (Rodessa) distillate stock, both oils in most cases containing as antioxidants 2 : 6-di-tert.-butyl-4-methylphenol and phenyl-a-naphthylamine. Other additives specified are pour point depressants, V.I. improvers, antidetonants, cetane number improvers, emulsifiers and thinners. Coating compositions.-The same corrosion inhibitors may be incorporated in paints, varnishes and lacquers, suitable vehicles including water, drying oils and asphalt roofing compositions.
GB20271/50A 1949-11-14 1950-08-15 Reaction products of n-acylated polyalkylenepolyamines with alkenyl succinic acids or anhydrides or derivatives thereof Expired GB684640A (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
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EP0377358A2 (en) * 1988-12-05 1990-07-11 Elf Antar France Nitrogen-bearing additives having antioxidant properties, and lubricant compositions comprising same
EP0388991A1 (en) * 1985-11-08 1990-09-26 The Lubrizol Corporation Fuel compositions
EP0721979A2 (en) * 1995-01-13 1996-07-17 Ciba-Geigy Ag Stabilized lubricant compositions
FR2753455A1 (en) * 1996-09-18 1998-03-20 Elf Antar France ADDITIVE DETERGENT AND ANTI-CORROSION FOR FUELS AND FUEL COMPOSITION
EP1645616A1 (en) * 2004-10-08 2006-04-12 Afton Chemical Corporation Power transmission fluids with enhanced antishudder durability
CN113698350A (en) * 2021-07-01 2021-11-26 新乡市瑞丰新材料股份有限公司 Preparation method and combined application of efficient imidazoline type antirust agent
CN114164430A (en) * 2021-11-30 2022-03-11 哈尔滨工业大学(深圳) Metal corrosion inhibitor and preparation method thereof

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0388991A1 (en) * 1985-11-08 1990-09-26 The Lubrizol Corporation Fuel compositions
EP0377358A2 (en) * 1988-12-05 1990-07-11 Elf Antar France Nitrogen-bearing additives having antioxidant properties, and lubricant compositions comprising same
EP0377358A3 (en) * 1988-12-05 1990-09-19 Elf France Nitrogen-bearing additives having antioxidant properties, and lubricant compositions comprising same
EP0721979A2 (en) * 1995-01-13 1996-07-17 Ciba-Geigy Ag Stabilized lubricant compositions
EP0721979A3 (en) * 1995-01-13 1997-04-16 Ciba Geigy Ag Stabilized lubricant compositions
WO1998012283A1 (en) * 1996-09-18 1998-03-26 Elf Antar France Detergent and anti-corrosive additive for fuels and fuel composition
FR2753455A1 (en) * 1996-09-18 1998-03-20 Elf Antar France ADDITIVE DETERGENT AND ANTI-CORROSION FOR FUELS AND FUEL COMPOSITION
US6083287A (en) * 1996-09-18 2000-07-04 Elf Antar France Detergent and anti-corrosive additive for fuels and fuel composition
EP1645616A1 (en) * 2004-10-08 2006-04-12 Afton Chemical Corporation Power transmission fluids with enhanced antishudder durability
KR100744983B1 (en) 2004-10-08 2007-08-02 에프톤 케미칼 코포레이션 Power transmission fluids with enhanced antishudder durability and handling characteristics
CN113698350A (en) * 2021-07-01 2021-11-26 新乡市瑞丰新材料股份有限公司 Preparation method and combined application of efficient imidazoline type antirust agent
CN114164430A (en) * 2021-11-30 2022-03-11 哈尔滨工业大学(深圳) Metal corrosion inhibitor and preparation method thereof
CN114164430B (en) * 2021-11-30 2023-06-20 哈尔滨工业大学(深圳) Metal corrosion inhibitor and preparation method thereof

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