EP1539677A2 - Succinic acid semi-amides as anti-corrosives agents - Google Patents

Succinic acid semi-amides as anti-corrosives agents

Info

Publication number
EP1539677A2
EP1539677A2 EP03757823A EP03757823A EP1539677A2 EP 1539677 A2 EP1539677 A2 EP 1539677A2 EP 03757823 A EP03757823 A EP 03757823A EP 03757823 A EP03757823 A EP 03757823A EP 1539677 A2 EP1539677 A2 EP 1539677A2
Authority
EP
European Patent Office
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.)
Withdrawn
Application number
EP03757823A
Other languages
German (de)
English (en)
French (fr)
Inventor
Hugo Camenzind
Peter Hänggi
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 SE
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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 Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Publication of EP1539677A2 publication Critical patent/EP1539677A2/en
Withdrawn legal-status Critical Current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 [having hydrocarbon substituents containing less than thirty carbon atoms]
    • 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 fulfil 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. Patent Specification 4462918 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. Patent Specification 5275749 discloses lubricant compositions providing protection against wear and corrosion, which comprise a component of the N-acyl-N-alkoxyalkylamino- succinic 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 a) At least one compound of formula
  • R 2 and R 3 are hydrogen, or one of R 2 and R 3 is hydrogen and the other is methyl;
  • X is carboxy or carboxylate and Y + is a salt-forming cation suitable for lubricant compositions;
  • R b and R c are each independently of the other hydrogen, CrC ⁇ alkyl or 2-hydroxyethyl, or R b and R 0 together are C 2 -C 8 alkylene, C 2 -C 8 alkenylene, C 2 -C 8 alkadienylene or C 2 -C 8 alkylene, C 2 -C 8 alkenylene or C 2 -C 8 alkadienylene interrupted by -O- or by -NR a - with R a being as defined; and
  • Y + is a hydrogen ion or is a salt-forming cation suitable for lubricant compositions; and b) A base oil of lubricating viscosity.
  • 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 2 and R 3 are hydrogen, or one of R 2 and R 3 is hydrogen and the other is methyl;
  • Y + is a hydrogen ion or is a salt-forming cation suitable for lubricant compositions; and b) A base oil of lubricating viscosity.
  • compositions comprising a) At least one compound (I), wherein
  • R 2 and R 3 are hydrogen
  • Y + is a hydrogen ion, ammonium, (CrC ⁇ alky ammonium or (2-hydroxyethyl) 1-4 - ammonium; and b) A base oil of lubricating viscosity.
  • a very especially preferred embodiment relates to compositions comprising a) At least one compound (I), wherein
  • Ri is a substituent selected from the group consisting of CrC 22 alkyl, C 3 -C 22 alkyl interrupted by -O-, phenyl, and benzyl;
  • R 2 and R 3 are hydrogen
  • X is derivatised carboxy selected from the group consisting of cyano, carboxy esterified by C 1 -C 22 alkyl, carboxy esterified by C 3 -C 22 alkyl interrupted by -O-, and carbamoyl of the partial formula (A) defined as piperidinocarbonyl, piperazinylcarbonyl or morpholi- nocarbonyl; and
  • Y + is a hydrogen ion, ammonium, (CrC ⁇ alkyl ⁇ ammonium or (2-hydroxyethyl) 1-4 - ammonium; and b) A base oil of lubricating viscosity.
  • compositions comprising a) At least one compound (I), wherein
  • R t is a substituent selected from the group consisting of CrC 18 alkyl, C 3 -C 18 alkyl interrupted by -O-, phenyl, and benzyl;
  • R 2 and R 3 are hydrogen
  • X is carboxy and Y is ammonium, (CrC alkyl) 1-4 ammonium or (2-hydroxyethyI) 1-4 - ammonium; or
  • X is carboxylate or derivatised carboxy selected from the group consisting of cyano, carboxy esterified by C ⁇ -C 18 alkyl, carboxy esterified by C 3 -C 18 alkyl interrupted by -O-, and morpholinocarbamoyl; and
  • Y + is hydrogen, ammonium, (C C 4 alkyl) 1-4 ammonium or (2-hydroxyethyl) 1-4 ammonium; and b) A base oil of lubricating viscosity.
  • the compounds (I) are prepared in a manner known per se, for example by addition of a primary amine R NH 2 to an acrylic acid derivative:
  • DE-A-2054649 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 t and R a defined as C ⁇ -C 22 alkyl include saturated, unbranched or, where possible, branched hydrocarbon groups, especially CrCgalkyl, e.g. methyl, ethyl, isopropyl, n-butyl, iso- butyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, 2-ethylbutyl, 1-methylpentyl, 1,3-di- methylbutyl, n-heptyl, 3-heptyl, 1-methylhexyl, isoheptyl, n-octyl, 2-ethylhexyl, 1 ,1,3,3-tetra- methylbutyl, 1 -methyl heptyl, n-nonyl or 1,1,3-trimethylhexyl, and also C 10 -C 22 alkyl, especially straight-chain C 10
  • Ri 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-hy- droxypropyl.
  • 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, tetraethylammo- nium or 2-hydroxyethyltrimethylammonium.
  • lubricant compositions e.g. ammonium, tetramethylammonium, tetraethylammo- nium 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 CrC 22 alkyl is, for example, a carboxy group which is esterified by the C C 22 alkyl groups defined hereinabove for R f e.g. saturated, unbranched or, where possible, branched hydrocarbon groups, e.g.
  • X defined as carboxy esterified by hydroxy-C 2 -C 22 aIkyl is, for example, a carboxy group that is esterified by hydroxy-C2-C22a!kyl defined hereinabove for R ⁇ e.g. 2-hydroxyethoxy- carbonyl or 2- or 3-hydroxypropoxycarbonyl.
  • X defined as carbamoyl of the partial formula A is, for example, carbamoyl, dimethyl- or di- ethyl-carbamoyl.
  • R and R 0 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 alka- dienylene, 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 Ri 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 + "a salt-forming cation suitable for lubricant compositions" is understood to mean those cations of salt-formers that together with the carboxylate group form suitable, non-metallic salts, e.g. ammonium, (CrC ⁇ alky ⁇ ammonium or (2-hydroxyethyl) 1-4 ammonium, e.g. tetramethylammonium, tet- raethylammonium or 2-hydroxyethyltrimethylammonium.
  • suitable, non-metallic salts e.g. ammonium, (CrC ⁇ alky ⁇ ammonium or (2-hydroxyethyl) 1-4 ammonium, e.g. tetramethylammonium, tet- raethylammonium 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.
  • 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-Pubiishers 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- oolef ins 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 Otto, 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 de- activators, rust inhibitors, viscosity index improvers, pour-point depressants, dispersants, detergents, extreme-pressure additives, anti-wear additives and friction reducers.
  • additives include: antioxidants, metal de- activators, rust inhibitors, viscosity index improvers, pour-point depressants, dispersants, detergents, extreme-pressure additives, anti-wear additives and friction reducers.
  • Such addi- tives 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 Phenolic antioxidants
  • 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-isobutyl- phenol, 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-methoxymethyl- phenol, linear nonylphenols or nonylphenols branched in the side-chain, e.g.
  • Alkylthiomethylphenols 2.4-dioctvlthiomethvl-6-tert-butylphenol. 2.4-dioctylthiomethyl-fi- methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol.
  • Hvdro ⁇ uinones and alkylated hvdroquinones 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-hy- droxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxy- phenyl) adipate.
  • Tocopherols ⁇ -, ⁇ -, ⁇ - or ⁇ -tocopherols and mixtures thereof (vitamin E).
  • Hvdroxylated thiodiphenyl ethers 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4- octylphenol), 4,4'-thiobis(6-tert-butyl-3-methyIphenol), 4,4'-thiobis(6-tert-butyl-2-methyl- phenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulphide.
  • Alkylidene 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-methylphe- nol), 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'-methyIenebis[6-( , ⁇ -dimethylbenzyl
  • N- and S-benzyl compounds S. ⁇ .S'. ⁇ '-tetra-tert-butyM ⁇ '-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.
  • Hvdroxybenzylated malonates dioctadecyl 2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malo- nate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, didodecylmercap- toethyl 2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, di-[4-(1 ,1 ,3,3-tetramethylbu- tyl)phenyl] 2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.
  • Hvdroxybenzyl 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)phenoI.
  • Triazine compounds 2.4-bisoctvlmercapto-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-octyl- mercapto-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) iso- cyanurate, 1 ,3,5-tris(4-tert-butyI-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-
  • 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-hvdroxyphenvQpropionic acid with mono- or poly-hydric alcohols for example with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-hex- anediol, 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, trimethyl- hexanediol, trimethylolpropane, 4-hydroxymethyl-1 -phospha-2,6,7-
  • esters of beta-(5-tert-butyl-4-hvdroxy-3-methylphenyl)propionic acid with mono- or polyhydric alcohols: with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-hexane- diol, 1 ,9-nonanediol, ethyiene 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, trimethyl- hexanediol, trimethylolpropane, 4-hydroxymethyl-1 -phospha-2,
  • esters of beta-(3,5-dicvclohexyl-4-hvdroxyphenv0propionic acid with mono- or poly-hydric alcohols e.g. with the alcohols mentioned under 13..
  • esters of 3.5-di-tert-butyl-4-hvdroxyphenylacetic acid with mono- or poly-hydric alcohols e.g. with the alcohols mentioned under 13..
  • Amides of beta-(3,5-di-tert-butyl-4-hvdroxyphenvhpropionic 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-hydroxy- phenyIpropionyl)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-
  • Metal deactivators for example for copper
  • Benzotriazoles and derivatives thereof 2-mercaptobenzotriazole, 2,5-dimercaptobenzo- triazole, 4- or 5-alkylbenzotriazoles (e.g. tolutriazole) and derivatives thereof, 4,5,6,7-tet- rahydrobenzotriazole, 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)ben- zotriazole, 1-(1-butoxyethyl)benzotriazole and 1-(1-cyclohexyloxybutyl)tolutriazole.
  • 2-mercaptobenzotriazole 2,5
  • Imidazole derivatives 4,4'-methylenebis(2-undecyl-5-methylimidazole); bis[(N-methyl)- imidazol-2-yl]carbinol-octyl ether.
  • Sulphur-containing heterocvclic compounds 2-mercaptobenzothiazole, 2,5-dimercapto- 1 ,3,4-thiadiazole, 2,5-dimercaptobenzothiadiazoIe and derivatives thereof; 3,5-bis[di(2- ethylhexyl)aminomethyl]-1,3,4-thiadiazolin-2-one.
  • Amino compounds salicylidene-propylenediamine, salicylaminoguanidine and salts thereof.
  • Tertiary aliphatic or cycloaliphatic amines and amine salts of organic and inorganic acids e.g. oil-soluble alkylammonium carboxylates, and also 1-[N,N-bis(2-hy- droxyethyl)amino]-3-(4-nonylphenoxy)propan-2-ol.
  • Heterocyclic compounds e.g. substituted imidazolines and oxazolines, e.g. 2-hepta- decenyl-1-(2-hydroxyethyl)-imidazoline.
  • 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-sulph- ides, benzotriazoles or derivatives thereof such as bis(2-ethylhexyl)aminomethyltolutriazole, dithiocarbamates such as methylene-bis-dibutyldithiocarbamate, derivatives of 2-mercapto- benzothiazole such as 1-[N,N-bis(2-ethylhexyl)aminomethyl]-2-mercapto-1H-1,3-benzothia- zole, derivatives of 2,5-dimercapto-1,3,4-thiadiazole such as 2,5-bis(tert-nonyldithio)-1 ,3,4- thiadiazole.
  • chlorinated paraffins for example, chlor
  • 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, polybutenylphos- phonic acid derivatives, basic magnesium, calcium and barium sulphonates and phe- nolates.
  • Emulsifiers petroleum sulphonates, amines, such as polyoxyethylated fatty amines, non- ionic surface-active substances; 2. Buffers: alkanolamines:
  • 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 perse. 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 ⁇ 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 speci- fication 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 AAWP 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):
  • FI ⁇ 2 is the requirement for passing the test.

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)
EP03757823A 2002-09-19 2003-09-11 Succinic acid semi-amides as anti-corrosives agents Withdrawn EP1539677A2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH20021588 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

Publications (1)

Publication Number Publication Date
EP1539677A2 true EP1539677A2 (en) 2005-06-15

Family

ID=32000111

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03757823A Withdrawn EP1539677A2 (en) 2002-09-19 2003-09-11 Succinic acid semi-amides as anti-corrosives agents

Country Status (12)

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

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY143758A (en) * 2004-09-13 2011-07-15 Ciba Holding Inc Polyolefin articles
KR20080049067A (ko) * 2005-09-28 2008-06-03 시바 홀딩 인코포레이티드 중합체 용융물의 유동성을 개선하는 방법
WO2007039521A1 (en) * 2005-09-30 2007-04-12 Ciba Specialty Chemicals Holding Inc. Microporous films
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
EP1925655A1 (en) 2006-11-22 2008-05-28 Infineum International Limited Lubricating oil compositions
JP5289759B2 (ja) * 2006-11-22 2013-09-11 インフィニューム インターナショナル リミテッド 潤滑油組成物
WO2010096286A1 (en) * 2009-02-18 2010-08-26 The Lubrizol Corporation Composition containing ester compounds and a method of lubricating an internal combustion engine
EP2230226B1 (en) 2009-03-18 2017-01-18 Infineum International Limited Additives for fuel oils
US20120136073A1 (en) 2010-11-15 2012-05-31 Life Technologies Corporation Amine-Containing Transfection Reagents and methods for making and using same
CA2860321A1 (en) * 2011-12-29 2013-07-04 The Lubrizol Corporation Limited slip friction modifiers for differentials
WO2016083090A1 (de) 2014-11-25 2016-06-02 Basf Se Korrosionsinhibitoren für kraft- und schmierstoffe
DE212016000150U1 (de) * 2015-07-24 2018-03-16 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

Family Cites Families (11)

* 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
GB2115000B (en) * 1982-02-17 1985-02-06 Shell Int Research Lubricating oils and hydraulic fluids
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
US4882077A (en) * 1988-03-09 1989-11-21 W. R. Grace & Co.-Conn. Metalworking fluid
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
JPH03122194A (ja) * 1989-10-05 1991-05-24 Nippon Oil Co Ltd 油組成物
GB8929096D0 (en) * 1989-12-22 1990-02-28 Ethyl Petroleum Additives Ltd Metal free lubricants
DK0565487T3 (da) 1992-04-08 1997-05-20 Ciba Geigy Ag Flydende antioxidanter som stabilisatorer
US5275749A (en) * 1992-11-06 1994-01-04 King Industries, Inc. N-acyl-N-hydrocarbonoxyalkyl aspartic acid esters as corrosion inhibitors
EP0810996B1 (en) * 1995-02-21 2002-10-09 Zhiqiang Alex He Imidazolidinone derivatives as corrosion inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004026811A2 *

Also Published As

Publication number Publication date
US20090221458A1 (en) 2009-09-03
US20050267003A1 (en) 2005-12-01
CN1308292C (zh) 2007-04-04
AU2003273857B2 (en) 2009-12-17
WO2004026811A3 (en) 2004-06-17
JP2005539120A (ja) 2005-12-22
KR20050046781A (ko) 2005-05-18
CA2496696C (en) 2013-01-22
AU2003273857A1 (en) 2004-04-08
JP4538795B2 (ja) 2010-09-08
BR0314307A (pt) 2005-07-05
MY146609A (en) 2012-09-14
WO2004026811A2 (en) 2004-04-01
TW200413285A (en) 2004-08-01
TWI330627B (en) 2010-09-21
MXPA05002726A (es) 2005-05-23
CA2496696A1 (en) 2004-04-01
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
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
ES2716233T3 (es) Composición lubricante que comprende ácido alquil éter carboxílico
JP4995086B2 (ja) アルキルアミノアセトアミド潤滑油添加剤
JPH0641161A (ja) 潤滑添加剤としてのジチオリン酸誘導体
US20120051965A1 (en) N-acylsarcosine compositions
JP4602768B2 (ja) 液体フェノール系硫黄含有抗酸化剤
US20040242437A1 (en) Antiwear performance of engine oils with $g(b)-dithiophosphorylated propionic acids
JP7004769B2 (ja) 組成物およびその形成方法
JP4558320B2 (ja) 抗酸化剤を有する水性機能液
JPH0641160A (ja) 潤滑剤添加剤としてのビスチオ燐酸誘導体
JP2008520784A (ja) ベンゾトリアゾール組成物
JP3211037B2 (ja) 多機能性潤滑剤用添加剤
US6255259B1 (en) Phosphorus-free multifunctional additives for lubricants
JPH06199852A (ja) 無リン潤滑剤添加剤

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20050204

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL LT LV MK

DAX Request for extension of the european patent (deleted)
RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: CIBA HOLDING INC.

17Q First examination report despatched

Effective date: 20110314

RIC1 Information provided on ipc code assigned before grant

Ipc: C10M 133/38 20060101AFI20120726BHEP

Ipc: C10M 133/50 20060101ALI20120726BHEP

Ipc: C10M 133/16 20060101ALI20120726BHEP

Ipc: C07C 235/74 20060101ALI20120726BHEP

Ipc: C07C 255/29 20060101ALI20120726BHEP

Ipc: C10M 133/24 20060101ALI20120726BHEP

Ipc: C10M 141/06 20060101ALI20120726BHEP

Ipc: C07C 237/22 20060101ALI20120726BHEP

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BASF SE

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20130115