US20050267003A1 - Succinic acid semi-amides as anti-corrosives agents - Google Patents

Succinic acid semi-amides as anti-corrosives agents Download PDF

Info

Publication number
US20050267003A1
US20050267003A1 US10/526,694 US52669405A US2005267003A1 US 20050267003 A1 US20050267003 A1 US 20050267003A1 US 52669405 A US52669405 A US 52669405A US 2005267003 A1 US2005267003 A1 US 2005267003A1
Authority
US
United States
Prior art keywords
alkyl
carboxy
hydrogen
interrupted
ammonium
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.)
Abandoned
Application number
US10/526,694
Other languages
English (en)
Inventor
Hugo Camenzind
Peter Hanggi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Corp
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Assigned to CIBA SPECIALTY CHEMICALS CORP. reassignment CIBA SPECIALTY CHEMICALS CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CAMENZIND, HUGO, HANGGI, PETER
Publication of US20050267003A1 publication Critical patent/US20050267003A1/en
Priority to US12/464,188 priority Critical patent/US20090221458A1/en
Abandoned legal-status Critical Current

Links

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
    • 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
    • C10M133/16—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • 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
    • 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
    • C10M133/24—Nitriles
    • 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
    • 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
    • C10M133/38—Heterocyclic nitrogen compounds
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/12—Partial amides of polycarboxylic acids
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/16—Nitriles
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • 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
    • 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
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • 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

Definitions

  • the present invention relates to compositions comprising succinic acid semi-amides and to the use of those compositions in improving the use properties of lubricants, such as hydraulic or metal-working fluids, greases, gear oils or engine oils.
  • lubricants such as hydraulic or metal-working fluids, greases, gear oils or engine oils.
  • Additives that have to fulfill demanding tasks are added to lubricants.
  • the properties of lubricants should not be modified disadvantageously in the presence of contaminants.
  • oils are admixed with commercially available additive concentrates or “packages”. Contamination with water, calcium detergents and residues of other lubricants may occur during the mixing process.
  • the action of the additive components with respect to corrosion is reduced, for example owing to formation of hydrolysis products and precipitation of poorly soluble calcium residues, the latter being especially disadvantageous because they block filter systems.
  • the present invention relates to the problem of producing lubricant compositions that provide improved protection against corrosion, combined with good compatibility with calcium ions.
  • U.S. Pat. No. 4,462,918 discloses lubricant compositions providing protection against wear and corrosion, which comprise a component of the N-acyl-N-alkylaminosuccinic acid ester type (aspartic acid esters, aspartates).
  • U.S. Pat. No. 5,275,749 discloses lubricant compositions providing protection against wear and corrosion, which comprise a component of the N-acyl-N-alkoxyalkylaminosuccinic acid ester type.
  • succinic acid semi-amides which are obtainable by reacting succinic acid anhydride with ⁇ -amino acid derivatives, improve the corrosion protection in lubricant compositions whilst at the same time the formation of precipitation products and residues is reduced.
  • compositions comprising
  • the compounds (I) have excellent corrosion-inhibiting action combined with good compatibility with calcium ions, which may be present in lubricants especially as constituents of detergents.
  • R 1 is a substituent selected from the group consisting of C 1 -C 22 alkyl, C 2 -C 22 alkyl substituted by hydroxy, C 2 -C 22 alkyl interrupted by —C( ⁇ O)—, —O—C( ⁇ O)— or by —NR a —C( ⁇ O)—, C 3 -C 22 alkyl interrupted by —O—, —S—, —NR a —, —C( ⁇ O)—O— or by C( ⁇ O)NR a , wherein R a denotes hydrogen or C 1 -C 22 alkyl, phenyl, benzyl, 1- or 2-phenylethyl, 2-phenoxyethyl, furfuryl, 1-naphthyl, 1-naphthylmethyl, cyclohexyl, cyclohexylmethyl and isobornyl;
  • the compounds (I) are prepared in a manner known per se, for example by addition of a primary amine R 1 —NH 2 to an acrylic acid derivative:
  • DE-A-2 054 649 describes the addition of primary amines to acrylic acid esters and the subsequent reaction with succinic anhydride.
  • the compounds described therein can be used, inter alia, as textile adjuvants.
  • R 1 and R a defined as C 1 -C 22 alkyl include saturated, unbranched or, where possible, branched hydrocarbon groups, especially C 1 -C 9 alkyl, e.g. methyl, ethyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, 2-ethylbutyl, 1-methylpentyl, 1,3-dimethylbutyl, n-heptyl, 3-heptyl, 1-methylhexyl, isoheptyl, n-octyl, 2-ethylhexyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, n-nonyl or 1,1,3-trimethylhexyl, and also C 10 -C 22 alkyl, especially straight-chain C 10 -C 22 alkyl
  • R 1 defined as C 2 -C 22 alkyl substituted by hydroxy includes saturated, unbranched hydrocarbon groups having preferably from 2 to 9 carbon atoms, e.g. 2-hydroxyethyl or 2- or 3-hydroxypropyl.
  • R 1 defined as C 2 -C 22 alkyl interrupted by —C( ⁇ O)—, —O—C( ⁇ O)— or by —NR a —C( ⁇ O)— includes unbranched or branched hydrocarbon groups preferably having from 2 to 9 carbon atoms, e.g. acetonyl, acetoxycarbonylmethyl, 2-acetoxycarbonylethyl, 2-tert-butoxycarbonylethyl or N,N-diethylcarbamoyl.
  • R 1 defined as C 3 -C 22 alkyl interrupted by —O—, —S—, —NR a —, —C( ⁇ O)—O— or by —C( ⁇ O)—NR a — includes unbranched or branched hydrocarbon groups preferably having from 3 to 18 carbon atoms, e.g.
  • R 2 and R 3 are hydrogen, or one of R 2 and R 3 is hydrogen and the other is methyl.
  • R 2 and R 3 are hydrogen.
  • Y + is a salt-forming cation suitable for lubricant compositions, e.g. ammonium, tetramethylammonium, tetraethylammonium or 2-hydroxyethyltrimethylammonium.
  • lubricant compositions e.g. ammonium, tetramethylammonium, tetraethylammonium or 2-hydroxyethyltrimethylammonium.
  • ammonium ions e.g. ammonium, tetramethylammonium, tetraethylammonium or 2-hydroxyethyltrimethylammonium.
  • X is derivatised carboxy or unsubstituted or substituted carbamoyl as defined hereinbelow.
  • Y + is then a hydrogen ion or a salt-forming cation suitable for lubricant compositions.
  • X defined as carboxy esterified by C 1 -C 22 alkyl is, for example, a carboxy group which is esterified by the C 1 -C 22 alkyl groups defined hereinabove for R 1 , e.g. saturated, unbranched or, where possible, branched hydrocarbon groups, e.g.
  • X defined as carboxy esterified by hydroxy-C 2 -C 22 alkyl is, for example, a carboxy group that is esterified by hydroxy-C2-C22alkyl defined hereinabove for R 1 , e.g. 2-hydroxyethoxycarbonyl or 2- or 3-hydroxypropoxycarbonyl.
  • X defined as carboxy esterified by C 2 -C 22 alkyl interrupted by —C( ⁇ O)—, —C( ⁇ O)—O— or by —C( ⁇ O)—NR a — is, for example, a carboxy group esterified by C 2 -C 22 alkyl, defined hereinabove for R 1 , interrupted by —C( ⁇ O)—, —C( ⁇ O)—O— or —C( ⁇ O)—NR a —, e.g. acetonyloxycarbonyl, acetoxycarbonylmethoxycarbonyl or 2-acetoxycarbonylethoxycarbonyl.
  • X defined as carboxy esterified by C 3 -C 22 alkyl interrupted by —O—, —S—, —NR a —, —O—C( ⁇ O)— or by —NR a —(C ⁇ O)— is, for example, a carboxy group esterified by C 3 -C 22 alkyl (defined hereinabove for R 1 ) interrupted by —O—, —S—, —NR a —, —O—C( ⁇ O)— or by —NR a —(C ⁇ O)—, e.g.
  • X defined as carbamoyl of the partial formula A is, for example, carbamoyl, dimethyl- or diethyl-carbamoyl.
  • R b and R c may be linked to one another by C 2 -C 8 alkylene, e.g. 1,4-n-butylene or 1,5-n-pentylene, by C 2 -C 8 alkenylene, e.g. 2-butenylene, or by C 2 -C 8 alkadienylene, e.g. 1,3-butadienylene and, together with —N ⁇ , form a heterocycle which may, in turn, contain further hetero atoms, e.g. N or O.
  • the partial formula A corresponds to a heterocyclylcarbonyl substituent, e.g. piperidinocarbonyl, piperazinylcarbonyl or morpholinocarbonyl.
  • the sum of the carbon atoms present in R 1 and X is preferably greater than ten.
  • Y + “a salt-forming cation suitable for lubricant compositions” includes those cations of salt-formers that together with the carboxylate group form metal salts suitable for lubricant compositions, e.g. alkali metal, alkaline earth metal, zinc (Zn 2+ ) or copper (Cu 2+ ) salts, e.g. sodium, potassium, calcium, zinc 2+ or Cu 2+ ions.
  • metal salts suitable for lubricant compositions e.g. alkali metal, alkaline earth metal, zinc (Zn 2+ ) or copper (Cu 2+ ) salts, e.g. sodium, potassium, calcium, zinc 2+ or Cu 2+ ions.
  • Y + “salt-forming cation suitable for lubricant compositions”
  • salt-formers that together with the carboxylate group form suitable, non-metallic salts, e.g. ammonium, (C 1 -C 22 alkyl) 1-4 ammonium or (2-hydroxyethyl) 1-4 ammonium, e.g. tetramethylammonium, tetraethylammonium or 2-hydroxyethyltrimethylammonium.
  • the compounds (I) are readily soluble in oils and can be admixed with a base oil of lubricating viscosity, e.g. a lubricant, in a manner known per se.
  • a base oil of lubricating viscosity e.g. a lubricant
  • base oil of lubricating viscosity includes, for example, lubricants that can be used for hydraulic or metal-working fluids, greases, gear oils or engine oils.
  • Suitable lubricants are based, for example, on mineral or synthetic oils or mixtures thereof.
  • the person skilled in the art will be familiar with the lubricants, which are described in the relevant technical literature, for example in Chemistry and Technology of Lubricants; Mortier, R. M. and Orszulik, S. T (Editors); 1992 Blackie and Son Ltd. for GB, VCH-Publishers N.Y. for U.S., ISBN 0-216-92921-0, see pages 208 ff and 269 ff; in Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition 1969, J. Wiley & Sons, New York, Vol. 13, page 533 ff (Hydraulic Fluids); Performance Testing of Hydraulic Fluids; R.
  • the lubricants are especially oils and greases, for example based on mineral oil or vegetable and animal oils, greases, tallow and wax or mixtures thereof.
  • Vegetable and animal oils, greases, tallow and wax are, for example, palm-kernel oil, palm oil, olive oil, rapeseed oil, rape oil, linseed oil, soybean oil, cottonseed oil, sunflower oil, coconut oil, maize oil, castor oil, tree nut oil and mixtures thereof, fish oils, and their chemically modified forms, for example epoxidised and sulphoxidised forms, or forms produced by genetic engineering, for example soybean oil produced by genetic engineering.
  • Examples of synthetic lubricants include lubricants based on aliphatic or aromatic carboxylic acid esters, polymeric esters, polyalkylene oxides, phosphoric acid esters, poly- ⁇ -olefins or silicones, diesters of a divalent acid with a monohydric alcohol, such as, for example, dioctyl sebacate or dinonyl adipate, triesters of trimethylolpropane with a monovalent acid or with a mixture of such acids, such as, for example, trimethylolpropane tripelargonate, trimethylolpropane tricaprylate or mixtures thereof, tetraesters of pentaerythritol with a monovalent acid or with a mixture of such acids, such as, for example, pentaerythritol tetracaprylate, or complex esters of monovalent and divalent acids with polyhydric alcohols, for example a complex ester of trimethylolpropane with capry
  • An organic or inorganic thickener can also be added to the mentioned lubricants or mixtures thereof (base grease).
  • Metal-working fluids and hydraulic fluids can be prepared on the basis of the same substances as described hereinabove for the lubricants. Such fluids are frequently also emulsions of such substances in water or other liquids.
  • compositions advantageously contain from 0.005 to 10.0% by weight, preferably from 0.01 to 5.0% by weight, especially from 0.01 to 0.9% by weight, of compounds (I).
  • compositions are used, for example, in hydraulic or metal-working fluids, greases, gear oils, or oils for engines of the Ofto, diesel, two-stroke, Wankel or orbital type.
  • the mentioned lubricants may additionally comprise other additives that are added in order to improve their basic properties still further; such additives include: antioxidants, metal deactivators, rust inhibitors, viscosity index improvers, pour-point depressants, dispersants, detergents, extreme-pressure additives, anti-wear additives and friction reducers.
  • additives include: antioxidants, metal deactivators, rust inhibitors, viscosity index improvers, pour-point depressants, dispersants, detergents, extreme-pressure additives, anti-wear additives and friction reducers.
  • additives are added in the customary amounts in each case, in the range of about from 0.01 to 10.0% by weight of each.
  • further additives are examples of further additives:
  • Alkylated monophenols 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-( ⁇ -methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, linear nonylphenols or nonylphenols branched in the side-chain, e.g.
  • Alkylthiomethylphenols 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol.
  • Hydroquinones and alkylated hydroquinones 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.
  • Tocopherols ⁇ -, ⁇ -, ⁇ - or ⁇ -tocopherols and mixtures thereof (vitamin E).
  • Hydroxylated thiodiphenyl ethers 2,2′-thiobis(6-tert-butyl-4-methylphenol), 2,2′-thiobis(4-octylphenol), 4,4′-thiobis(6-tert-butyl-3-methylphenol), 4,4′-thiobis(6-tert-butyl-2-methylphenol), 4,4′-thiobis(3,6-di-sec-amylphenol), 4,4′-bis(2,6-dimethyl-4-hydroxyphenyl) disulphide.
  • Alkenylene bisphenols 2,2′-methylenebis(6-tert-butyl-4-methylphenol), 2,2′-methylene-bis(6-tert-butyl-4-ethylphenol), 2,2′-methylenebis[4-methyl-6-( ⁇ -methylcyclohexyl)phenol], 2,2′-methylenebis(4-methyl-6-cyclohexylphenol), 2,2′-methylenebis(6-nonyl-4-methylphenol), 2,2′-methylenebis(4,6-di-tert-butylphenol), 2,2′-ethylidenebis(4,6-di-tert-butylphenol), 2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2′-methylenebis[6-( ⁇ -methylbenzyl)-4-nonylphenol], 2,2′-methylenebis[6-( ⁇ , ⁇ -dimethylbenzyl)-4-nonylphenol], 4,
  • O-, N- and S-benzyl compounds 3,5,3′,5′-tetra-tert-butyl-4,4′-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl mercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzyl mercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl) sulphide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate.
  • Hydroxybenzylated malonates dioctadecyl 2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, didodecylmercaptoethyl 2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, di-[4-(1,1,3,3-tetramethylbutyl)phenyl]2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.
  • Hydroxybenzyl aromatic compounds 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.
  • Triazine comoounds 2,4-bisoctylmercapto-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-tris(3,3,
  • Acylaminophenols 4-hydroxylauric acid anilide, 4-hydroxystearic acid anilide, N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamic acid octyl ester.
  • esters of beta-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or poly-hydric alcohols for example with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) isocyanurate, N,N′-bis(hydroxyethyl)oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2
  • esters of beta-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with mono- or poly-hydric alcohols: with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) isocyanurate, N,N′-bis(hydroxyethyl)oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]
  • esters of beta-(3.5-dicyclohexyl-4-hydroxyphenyl)progionic acid with mono- or poly-hydric alcohols e.g. with the alcohols mentioned under 13.
  • esters of 3.5-di-tert-butyl-4-hydroxyphenylacetic acid with mono- or poly-hydric alcohols e.g. with the alcohols mentioned under 13.
  • Amides of beta-(3.5-di-tert-butyl-4-hydroxphenyl)propionic acid for example N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine.
  • vitamin C Ascorbic acid (vitamin C), aliphatic or aromatic phosphites, esters of thiodipropionic acid or thiodiacetic acid, or salts of dithiocarbamic or dithiophosphoric acid, 2,2,12,12-tetramethyl-5,9-dihydroxy-3,7,11-trithiatridecane and 2,2,15,15-tetramethyl-5,12-dihydroxy-3,7,10,14-tetrathiahexadecane.
  • Benzotriazoles and derivatives thereof 2-mercaptobenzotriazole, 2,5-dimercaptobenzotriazole, 4- or 5-alkylbenzotriazoles (e.g. tolutriazole) and derivatives thereof, 4,5,6,7-tetrahydrobenzotriazole, 5,5′-methylene-bisbenzotriazole; Mannich bases of benzotriazole or tolutriazole, such as 1-[di(2-ethylhexyl)aminomethyl]tolutriazole and 1-[di(2-ethylhexyl)-aminomethyl]benzotriazole; alkoxyalkylbenzotriazoles, such as 1-(nonyloxymethyl)benzotriazole, 1-(1-butoxyethyl)benzotriazole and 1-(1-cyclohexyloxybutyl)tolutriazole.
  • 2-mercaptobenzotriazole 2,5-dimercaptobenz
  • 1,2,4-Triazoles and derivatives thereof 3-alkyl- (or aryl-)1,2,4-triazoles, Mannich bases of 1,2,4-triazoles, such as 1-[di(2-ethylhexyl)aminomethyl]-1,2,4-triazole; alkoxyalkyl-1,2,4-triazoles, such as 1-(1-butoxyethyl)-1,2,4-triazole; acylated 3-amino-1,2,4-triazoles.
  • Imidazole derivatives 4,4′-methylenebis(2-undecyl-5-methylimidazole); bis[(N-methyl)-imidazol-2-yl]carbinol-octyl ether.
  • Sulphur-containing heterocyclic compounds 2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercaptobenzothiadiazole and derivatives thereof; 3,5-bis[di(2-ethylhexyl)aminomethyl]-1,3,4-thiadiazolin-2-one.
  • Amino compounds salicylidene-propylenediamine, salicylaminoguanidine and salts thereof.
  • Sulphur-containing compounds barium dinonylnaphthalenesulphonates, calcium petroleum sulphonates, alkylthio-substituted aliphatic carboxylic acids, esters of aliphatic 2-sulphocarboxylic acids and salts thereof.
  • Sulphur-containing and halogen-containing compounds for example, chlorinated paraffins, sulphurated olefins or vegetable oils (soybean/rapeseed oil), alkyl- or aryl-di- or -tri-sulphides, benzotriazoles or derivatives thereof such as bis(2-ethylhexyl)aminomethyltolutriazole, dithiocarbamates such as methylene-bis-dibutyidithiocarbamate, derivatives of 2-mercaptobenzothiazole such as 1-[N,N-bis(2-ethylhexyl)aminomethyl]-2-mercapto-1 H-1,3-benzothiazole, derivatives of 2,5-dimercapto-1,3,4thiadiazole such as 2,5-bis(tert-nonyldithio)-1,3,4-thiadiazole.
  • chlorinated paraffins for example, chlorinated paraffins, sulph
  • Viscosity Index improvers polyacrylates, polymethacrylates, vinylpyrrolidone/methacrylate copolymers, polyvinylpyrrolidones, polybutenes, olefin copolymers, styrene/acrylate co-polymers, polyethers.
  • pour-point depressants poly(meth)acrylates, ethylene/vinyl acetate copolymer, alkyl-polystyrenes, fumarate copolymers, alkylated naphthalene derivatives.
  • Dispersants/surfactants polybutenylsuccinic acid amides or imides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulphonates and phenolates.
  • Emulsifiers petroleum sulphonates, amines, such as polyoxyethylated fatty amines, non-ionic surface-active substances;
  • Biocides triazines, thiazolinones, tris-nitromethane, morpholine, sodium pyridenethiol;
  • Processing speed improvers calcium and barium sulphonates.
  • the mentioned ingredients are added to the composition using customary mixing methods in a manner known per se. It is also possible, using the compounds (I) or mixtures thereof and, optionally, further additives, to prepare a concentrate or so-called additive package, which is diluted, as required for use, to a concentration for use in the lubricant in question.
  • the composition of the components in the concentrate is such that the concentrate is liquid at room temperature without further addition of component b) or a solvent.
  • the present invention relates also to a concentrate comprising a) at least one compound (I) wherein R 1 , R 2 , R 3 , X and Y are as defined, optionally further additives, and b) a base oil of lubricating viscosity.
  • the invention relates also to a method of improving the use properties of lubricants, which comprises adding to the lubricants a composition comprising at least one compound (I) wherein R 1 , R 2 , R 3 , X and Y are as defined.
  • 300 ml of formulated oil are mixed with 30 ml of synthetic seawater by stirring for 24 h at 60° whilst simultaneously immersing a steel round-section bar.
  • the steel bar After being in contact for that period, the steel bar is subjected to a visual corrosion test. Each test is carried out in duplicate.
  • the base formulation is based on a mineral oil of specification SN VG46, which has been stabilised using antioxidants and metal deactivators.
  • the active ingredients under test are used in a concentration of 0.1 mmol/kg (corresponding to 0.03-0.06% by weight or 300-600 ppm). See Table 2 for results.
  • 0.3 g of distilled water and 30 ppm of calcium in the form of a calcium detergent (6.9% Ca) are added to 300 g of the test formulation.
  • the mixture is homogenised in a four-blade mixer at the maximum speed of rotation for 5 min.
  • the emulsion is stored for 96 hours at 70° C. (+/ ⁇ 2° C.) and then for a further 48 hours at room temperature in the dark. If precipitation is observed, the test is stopped. Before filtration, the test mixture is homogenised again by shaking vigorously for one minute. It is then filtered through a 0.8 ⁇ Millipore® filter (type MWP 04700) using compressed air at 1 bar (+/ ⁇ 0.05 bar) positive pressure. The times required to filter 50, 100, 200 and 300 ml of test mixture are measured.
  • the filtration index FI is calculated, as the mean of two measurements, in accordance with the following formula (see AFNOR NFE 48-691):

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US10/526,694 2002-09-19 2003-09-11 Succinic acid semi-amides as anti-corrosives agents Abandoned US20050267003A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/464,188 US20090221458A1 (en) 2002-09-19 2009-05-12 Succinic acid semi-amides as anti-corrosive agents

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH20021588/02 2002-09-19
CH15882002 2002-09-19
PCT/EP2003/010115 WO2004026811A2 (en) 2002-09-19 2003-09-11 Succinic acid semi-amides as anti-corrosives agents

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/464,188 Continuation US20090221458A1 (en) 2002-09-19 2009-05-12 Succinic acid semi-amides as anti-corrosive agents

Publications (1)

Publication Number Publication Date
US20050267003A1 true US20050267003A1 (en) 2005-12-01

Family

ID=32000111

Family Applications (2)

Application Number Title Priority Date Filing Date
US10/526,694 Abandoned US20050267003A1 (en) 2002-09-19 2003-09-11 Succinic acid semi-amides as anti-corrosives agents
US12/464,188 Abandoned US20090221458A1 (en) 2002-09-19 2009-05-12 Succinic acid semi-amides as anti-corrosive agents

Family Applications After (1)

Application Number Title Priority Date Filing Date
US12/464,188 Abandoned US20090221458A1 (en) 2002-09-19 2009-05-12 Succinic acid semi-amides as anti-corrosive agents

Country Status (12)

Country Link
US (2) US20050267003A1 (ja)
EP (1) EP1539677A2 (ja)
JP (1) JP4538795B2 (ja)
KR (1) KR20050046781A (ja)
CN (1) CN1308292C (ja)
AU (1) AU2003273857B2 (ja)
BR (1) BR0314307A (ja)
CA (1) CA2496696C (ja)
MX (1) MXPA05002726A (ja)
MY (1) MY146609A (ja)
TW (1) TWI330627B (ja)
WO (1) WO2004026811A2 (ja)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070244233A1 (en) * 2004-09-13 2007-10-18 David Hild Polyolefin Articles
EP1925655A1 (en) 2006-11-22 2008-05-28 Infineum International Limited Lubricating oil compositions
US20090258560A1 (en) * 2005-09-30 2009-10-15 Per Magnus Kristiansen Microporous Films
US20090318593A1 (en) * 2005-09-28 2009-12-24 Klaus Stoll Process for Improving the Flow Properties of Polymer Melts
US20100236139A1 (en) * 2009-03-18 2010-09-23 Graham Jackson Additives for Fuel Oils
US20120021956A1 (en) * 2009-02-18 2012-01-26 The Lubrizol Corporation Composition Containing Ester Compounds and a Method of Lubricating an Internal Combustion Engine

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5224571B2 (ja) * 2006-10-26 2013-07-03 協同油脂株式会社 グリース組成物及び軸受
CA2612055C (en) * 2006-11-22 2015-05-26 Infineum International Limited Lubricating oil compositions comprising 4-oxobutanoic acid derivatives
CN108358812B (zh) 2010-11-15 2021-05-11 生命技术公司 含胺的转染试剂及其制备和使用方法
AU2012362446A1 (en) * 2011-12-29 2014-07-17 The Lubrizol Corporation Limited slip friction modifiers for differentials
DE212015000271U1 (de) 2014-11-25 2017-09-06 Basf Se Korrosionsinhibitoren für Kraft- und Schmierstoffe
WO2017016909A1 (de) * 2015-07-24 2017-02-02 Basf Se Korrosionsinhibitoren für kraft- und schmierstoffe
GB201703615D0 (en) * 2017-03-07 2017-04-19 Univ I Stavanger Method of inhibiting the agglomeration of gas hydrates

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4462918A (en) * 1982-02-17 1984-07-31 Shell Oil Company Lubricating oil composition
US4882077A (en) * 1988-03-09 1989-11-21 W. R. Grace & Co.-Conn. Metalworking fluid
US5275749A (en) * 1992-11-06 1994-01-04 King Industries, Inc. N-acyl-N-hydrocarbonoxyalkyl aspartic acid esters as corrosion inhibitors
US5362375A (en) * 1989-10-05 1994-11-08 Nippon Oil Co., Ltd. Oil compositions

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2054649A1 (de) * 1970-11-06 1972-05-10 Chemische Werke Hüls AG, 4370 Mari Verfahren zur Herstellung von Salzen von N-Acyl-N alkylaminopropionsäuren
JPS62290799A (ja) * 1986-06-09 1987-12-17 Idemitsu Kosan Co Ltd 摺動面兼金属加工油剤および該摺動面兼金属加工油剤を用いた工作機械の潤滑方法
US5091099A (en) * 1988-06-09 1992-02-25 Ciba-Geigy Corporation Lubricating oil composition
US5073278A (en) * 1988-07-18 1991-12-17 Ciba-Geigy Corporation Lubricant composition
GB8929096D0 (en) * 1989-12-22 1990-02-28 Ethyl Petroleum Additives Ltd Metal free lubricants
DE59306149D1 (de) 1992-04-08 1997-05-22 Ciba Geigy Flüssige Antioxidantien als Stabilisatoren
JPH11504315A (ja) * 1995-02-21 1999-04-20 ヘ，ジジャン・アレックス 腐食抑制剤としてのイミダゾリジノン誘導体

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4462918A (en) * 1982-02-17 1984-07-31 Shell Oil Company Lubricating oil composition
US4882077A (en) * 1988-03-09 1989-11-21 W. R. Grace & Co.-Conn. Metalworking fluid
US5362375A (en) * 1989-10-05 1994-11-08 Nippon Oil Co., Ltd. Oil compositions
US5275749A (en) * 1992-11-06 1994-01-04 King Industries, Inc. N-acyl-N-hydrocarbonoxyalkyl aspartic acid esters as corrosion inhibitors

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070244233A1 (en) * 2004-09-13 2007-10-18 David Hild Polyolefin Articles
US7476713B2 (en) 2004-09-13 2009-01-13 Ciba Specialty Chemicals Corp. Polyolefin articles
US20090318593A1 (en) * 2005-09-28 2009-12-24 Klaus Stoll Process for Improving the Flow Properties of Polymer Melts
US20090258560A1 (en) * 2005-09-30 2009-10-15 Per Magnus Kristiansen Microporous Films
EP1925655A1 (en) 2006-11-22 2008-05-28 Infineum International Limited Lubricating oil compositions
US20120021956A1 (en) * 2009-02-18 2012-01-26 The Lubrizol Corporation Composition Containing Ester Compounds and a Method of Lubricating an Internal Combustion Engine
US8921288B2 (en) * 2009-02-18 2014-12-30 The Lubrizol Corporation Composition containing ester compounds and a method of lubricating an internal combustion engine
US9765275B2 (en) * 2009-02-18 2017-09-19 The Lubrizol Corporation Composition containing ester compounds and a method of lubricating an internal combustion engine
US20100236139A1 (en) * 2009-03-18 2010-09-23 Graham Jackson Additives for Fuel Oils
US10308593B2 (en) * 2009-03-18 2019-06-04 Infineum International Limited Additives for fuel oils

Also Published As

Publication number Publication date
US20090221458A1 (en) 2009-09-03
TWI330627B (en) 2010-09-21
CA2496696A1 (en) 2004-04-01
KR20050046781A (ko) 2005-05-18
JP4538795B2 (ja) 2010-09-08
CN1308292C (zh) 2007-04-04
TW200413285A (en) 2004-08-01
EP1539677A2 (en) 2005-06-15
AU2003273857B2 (en) 2009-12-17
JP2005539120A (ja) 2005-12-22
WO2004026811A2 (en) 2004-04-01
AU2003273857A1 (en) 2004-04-08
MY146609A (en) 2012-09-14
WO2004026811A3 (en) 2004-06-17
BR0314307A (pt) 2005-07-05
CA2496696C (en) 2013-01-22
MXPA05002726A (es) 2005-05-23
CN1681772A (zh) 2005-10-12

Similar Documents

Publication Publication Date Title
US20090221458A1 (en) Succinic acid semi-amides as anti-corrosive agents
RU2483099C2 (ru) Замедляющая коррозию композиция для цветных металлов
JP4114180B2 (ja) チオリン酸エステルとジチオリン酸エステルを含有する改善潤滑剤組成物
EP1861485B1 (en) Antiwear lubricant compositions for use in combustion engines
JP4838133B2 (ja) ボレートエステル潤滑添加剤
US8329625B2 (en) Aqueous functional fluids with antioxidants
JPH0641161A (ja) 潤滑添加剤としてのジチオリン酸誘導体
US20020065201A1 (en) Lubricants with 5-tert.-butyl-4-hydroxy-3-methylphenyl substituted fatty acid esters
US20120051965A1 (en) N-acylsarcosine compositions
JP4602768B2 (ja) 液体フェノール系硫黄含有抗酸化剤
JP2008520784A (ja) ベンゾトリアゾール組成物
US20040242437A1 (en) Antiwear performance of engine oils with $g(b)-dithiophosphorylated propionic acids
KR100274362B1 (ko) 윤활 첨가제로서 유용한 비스디티오인산 유도체
US6255259B1 (en) Phosphorus-free multifunctional additives for lubricants

Legal Events

Date Code Title Description
AS Assignment

Owner name: CIBA SPECIALTY CHEMICALS CORP., NEW YORK

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CAMENZIND, HUGO;HANGGI, PETER;REEL/FRAME:016944/0774

Effective date: 20050127

STCB Information on status: application discontinuation

Free format text: ABANDONED -- AFTER EXAMINER'S ANSWER OR BOARD OF APPEALS DECISION