AU2003273857B2 - Succinic acid semi-amides as anti-corrosives agents - Google Patents

Description

WO 2004/026811 PCT/EP2003/010115 Succinic acid semi-amides as anti-corrosive agents 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. Additives that have to fulfil demanding tasks, such as a high load-bearing capacity, protection against wear and corrosion, and antioxidant action, are added to lubricants. In addition, the properties of lubricants should not be modified disadvantageously in the presence of con taminants. Often, in mineral oil industry enterprises, oils are admixed with commercially avai lable additive concentrates or "packages". Contamination with water, calcium detergents and residues of other lubricants may occur during the mixing process. As a result, 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 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. Patent Specification 5 275 749 discloses lubricant compositions providing protection against wear and corrosion, which comprise a component of the N-acyl-N-alkoxyalkylamino succinic acid ester type. It has now been found, surprisingly, that succinic acid semi-amides, which are obtainable by reacting succinic acid anhydride with p-amino acid derivatives, improve the corrosion protec tion in lubricant compositions whilst at the same time the formation of precipitation products and residues is reduced. The invention relates to compositions comprising a) At least one compound of formula

R

2 Ri-...N' X 0 R3 0

O"Y+

WO 2004/026811 PCT/EP2003/010115 -2 Wherein

R

1 is a substituent selected from the group consisting of C-C 2 2 alkyl, C 2

-C

22 alkyl sub stituted by hydroxy, C 2

-C

22 alkyl interrupted by -C(=O)-, -O-C(=O)- or by -NRa-C(=0)-, C 3

-C

22 alkyl interrupted by -0-, -S-, -NRa-, -C(=O)-O- or by -C(=0)-NRa-, wherein Ra denotes hydrogen or C-C 2 2 alkyl, phenyl, benzyl, 1- or 2-phenylethyl, 2-phenoxyethyl, furfuryl, 1-naphthyl, 1-naphthylmethyl, cyclohexyl, cyclohexylmethyl, and isobornyl;

R

2 and R 3 are hydrogen, or one of R 2 and R 3 is hydrogen and the other is methyl; and X is carboxy or carboxylate and Y* is a salt-forming cation suitable for lubricant com positions; or X is derivatised carboxy selected from the group consisting of cyano, carboxy esteri fied by C-C 2 2 alkyl, carboxy esterified by hydroxy-C 2

-C

2 2 alkyl, carboxy esterified by

C

2

-C

22 alkyl interrupted by -C(=O)-, -C(=O)-O- or by -C(=O)-NRa-, carboxy esterified by C 3

-C

2 2 alkyl interrupted by -0-, -S-, -NRa-, -O-C(=O)- or by -NRa-(C=O)-, wherein Ra denotes hydrogen or C-C 2 2 alkyl, carboxy esterified by phenyl, benzyl, 1- or 2-phenylethyl, 2-phenoxyethyl, furfuryl, 1-naphthyl, 1 -naphthylmethyl, cyclohexyl, cyclohexylmethyl, isobornyl, and carbamoyl of the partial formula 0 NRb (A), Wherein Rb and R, are each independently of the other hydrogen, C-C 22 alkyl or 2-hydroxyethyl, or Rb and R, together are C 2

-C

8 alkylene, C 2

-C

8 alkenylene,

C

2 -Csalkadienylene or C 2

-C

8 alkylene, C 2 -Cealkenylene or C 2

-C

8 alkadienylene inter rupted by -0- or by -NRa- with Ra 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 (1) have excellent corrosion-inhibiting action combined with good compatibil ity with calcium ions, which may be present in lubricants especially as constituents of deter gents. A preferred embodiment relates to compositions comprising a) At least one compound (1), wherein WO 2004/026811 PCT/EP2003/010115 -3

R

1 is a substituent selected from the group consisting of C-C 22 alkyl, C 2

-C

22 alkyl substi tuted by hydroxy, C 2

-C

2 2 alkyl interrupted by -C(=O)-, -0-C(=O)- or by -NRa-C(=0)-,

C

3

-C

22 alkyl interrupted by -0-, -S-, -NRa-, -C(=O)-O- or by -C(=0)-NRa-, wherein Ra de notes hydrogen or C-C 2 2 alkyl, phenyl, benzyl, 1- or 2-phenylethyl, 2-phenoxyethyl, furfuryl, 1 -naphthyl, 1 -naphthylmethyl, cyclohexyl, cyclohexylmethyl and isobornyl;

R

2 and R 3 are hydrogen, or one of R 2 and R 3 is hydrogen and the other is methyl; X is derivatised carboxy selected from the group consisting of cyano, carboxy esterified by C-C 2 2 alkyl, carboxy esterified by hydroxy-C 2

-C

2 2 alkyl, carboxy esterified by

C

2

-C

22 alkyl interrupted by -C(=O)-, -C(=O)-O- or by -C(=O)-NRa-, carboxy esterified by

C

3

-C

22 alkyl interrupted by -0-, -S-, -NRa-, -0-C(=0)- or by -NRa-(C=O)-, wherein Ra de notes hydrogen or C-C 2 2 alkyl, carboxy esterified by phenyl, benzyl, 1- or 2-phenylethyl, 2-phenoxyethyl, furfuryl, 1-naphthyl, 1 -naphthylmethyl, cyclohexyl, cyclohexylmethyl, isobornyl, and carbamoyl of the partial formula (A), wherein Rb and Rc are each inde pendently of the other hydrogen, C-C 2 2 alkyl or 2-hydroxyethyl, or Rb and R, 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 -Csalk enylene or C 2 -Csalkadienylene interrupted by -0- or by -NRa-, Ra 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. An especially preferred embodiment corresponds to the following compositions comprising a) At least one compound (1), wherein

R

1 is a substituent selected from the group consisting of C-C 2 2 alkyl, C 2

-C

2 2 alkyl inter rupted by -C(=0)- or by -0-C(=O)-, C 3

-C

2 2 alkyl interrupted by -0- , -S- or by -C(=0)-0-, 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-C 2 2 alkyl, carboxy esterified by hydroxy-C 2

-C

2 2 alkyl, carboxy esterified by

C

2

-C

22 alkyl interrupted by -C(=O)- or by -C(=0)-0-, carboxy esterified by C 3

-C

2 2 alkyl interrupted by -0-, -S- or by -0-C(=0)-, and carbamoyl of the partial formula (A) defined as heterocyclylcarbonyl; and Y* is a hydrogen ion, ammonium, (C-C 4 alkyl) 1

.

4 ammonium or (2-hydroxyethyl) 14 ammonium; and b) A base oil of lubricating viscosity.

WO 2004/026811 PCT/EP2003/010115 -4 A very especially preferred embodiment relates to compositions comprising a) At least one compound (I), wherein

R

1 is a substituent selected from the group consisting of C1-C 22 alkyl, C 3

-C

22 alkyl inter rupted by -0-, 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

2 2 alkyl interrupted by -0-, and carbamoyl of the partial formula (A) defined as piperidinocarbonyl, piperazinylcarbonyl or morpholi nocarbonyl; and Y+ is a hydrogen ion, ammonium, (C-C 4 alkyl) 1 .4ammonium or (2-hydroxyethyl) 1

.

4 ammonium; and b) A base oil of lubricating viscosity. A likewise very especially preferred embodiment relates to compositions comprising a) At least one compound (I), wherein

R

1 is a substituent selected from the group consisting of C 1

-C

18 alkyl, C-C 1 8 alkyl interrupted by -0-, phenyl, and benzyl;

R

2 and R 3 are hydrogen; X is carboxy and Y is ammonium, (C-C 4 alkyl) 1 .4ammonium or (2-hydroxyethyl) 1

.

4 ammonium; or X is carboxylate or derivatised carboxy selected from the group consisting of cyano, car boxy esterified by C-C 1 8 alkyl, carboxy esterified by C-C 1 8 alkyl interrupted by -0-, and morpholinocarbamoyl; and Y+ is hydrogen, ammonium, (C-C 4 alkyl) 1 .4ammonium or (2-hydroxyethyl) 1 .4ammonium; 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:

R

2 X H R 3 (X = carboxy, carboxylate or derivatised carboxy) (Addition of amines to a,p-unsaturated carbonyl compounds) to form a p-amino acid deriva tive: WO 2004/026811 PCT/EP2003/010115 -5

R

2 R X H

R

3 Which is acylated with a reactive, functional derivative of succinic acid, for example succinic anhydride or succinic acid monochloride. DE-A-2 054 649 describes the addition of primary amines to acrylic acid esters and the sub sequent reaction with succinic anhydride. The compounds described therein can be used, inter alia, as textile adjuvants. The terms and general designations used in the description of the present invention are pref erably defined as follows: Component a) Compounds (I)

R

1 and Ra defined as C 1

-C

22 alkyl include saturated, unbranched or, where possible, bran ched hydrocarbon groups, especially C-Coalkyl, 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 -methylheptyl, n-nonyl or 1,1,3-trimethylhexyl, and also C 1

O-C

22 alkyl, especially straight-chain C 1

O-C

22 alkyl, e.g. n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl or n-octadecyl or branched C 10

-C

22 alkyl, e.g. 1,1,3-trimethylhexyl, 1-methylundecyl, 2-n-butyl-n-octyl, isotridecyl, 2-n-hexyl-n-decyl or 2-n-octyl-n-dodecyl, or higher homologues thereof.

R

1 defined as C 2

-C

22 alkyl substituted by hydroxy includes saturated, unbranched hydrocar bon groups having preferably from 2 to 9 carbon atoms, e.g. 2-hydroxyethyl or 2- or 3-hy droxypropyl.

R

1 defined as C 2

-C

22 alkyl interrupted by -C(=O)-, -O-C(=O)- or by -NRa-C(=O)- includes un branched 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 -0-, -S-, -NRa-, -C(=O)-O- or by -C(=O)-NRa- in cludes unbranched or branched hydrocarbon groups preferably having from 3 to 18 carbon atoms, e.g. 2-methoxyethyl, 2- or 3-methoxypropyl, 2-, 3- or 4-methoxybutyl, 2-ethoxyethyl, 2- or 3-ethoxypropyl, 2-, 3- or 4-ethoxybutyl, 2-n-propoxyethyl, 2- or 3-n-propoxypropyl, 2-, 3 or 4-n-propoxybutyl, 2-isopropoxyethyl, 2- or 3-isopropoxypropyl, 2-, 3- or 4-isopropoxybutyl, 2-n-butoxyethyl, 2- or 3-n-butoxypropyl, 2-, 3- or 4-n-butoxybutyl, 2-tert-butoxyethyl, 2- or 3-tert-butoxypropyl, 2-, 3- or 4-tert-butoxybutyl, 2-methylthioethyl, 2- or 3-methylthiopropyl, 2- WO 2004/026811 PCT/EP2003/010115 -6 ethylthioethyl, 2-dimethylaminoethyl, 2- or 3-dimethylaminopropyl, 2-diethylaminoethyl, 2- or 3-diethylaminopropyl, 2-acetoxyethyl or 2-(N-acetoxy-N-methyl)-ethyl. In compounds (I), R 2 and R 3 are hydrogen, or one of R 2 and R 3 is hydrogen and the other is methyl. Preferably, R 2 and R 3 are hydrogen. When X in compounds (1) is carboxy or carboxylate [-C(=O)-O~], Y' is a salt-forming cation suitable for lubricant compositions, e.g. ammonium, tetramethylammonium, tetraethylammo nium or 2-hydroxyethyltrimethylammonium. There is present only one carboxy group in sub stantially undissociated form [-C(=O)-OH] or in salt form [-C(=O)-O~], e.g. with ammonium ions, e.g. ammonium, tetramethylammonium, tetraethylammonium or 2-hydroxyethyl trimethylammonium. In a preferred embodiment, X is derivatised carboxy or unsubstituted or substituted car bamoyl 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

2 2 alkyl is, for example, a carboxy group which is es terified by the C 1

-C

2 2 alkyl groups defined hereinabove for R 1 , e.g. saturated, unbranched or, where possible, branched hydrocarbon groups, e.g. methyl, ethyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, 2-ethylbutyl, 1-methylpentyl, 1,3-dimethyl butyl, n-heptyl, 3-heptyl, 1-methylhexyl, isoheptyl, n-octyl, 2-ethylhexyl, 1,1,3,3-tetramethyl butyl, 1 -methylheptyl, n-nonyl or 1,1,3-trimethylhexyl, and also by C 1

O-C

2 2 alkyl, especially straight-chain C1 0

-C

2 2 alkyl, e. g. n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl or n-octadecyl. X defined as carboxy esterified by hydroxy-C 2

-C

2 2 alkyl is, for example, a carboxy group that is esterified by hydroxy-C2-C22alkyl defined hereinabove for R 1 , e.g. 2-hydroxyethoxy carbonyl or 2- or 3-hydroxypropoxycarbonyl. X defined as carboxy esterified by C 2

-C

2 2 alkyl interrupted by -C(=O)-, -C(=O)-O- or by -C(=0)-NRa- is, for example, a carboxy group esterified by C 2

-C

2 2 alkyl, defined hereinabove for R 1 , interrupted by -C(=O)-, -C(=O)-O- or -C(=0)-NRa-, e.g. acetonyloxycarbonyl, acetoxy carbonylmethoxycarbonyl or 2-acetoxycarbonylethoxycarbonyl. X defined as carboxy esterified by C 3

-C

22 alkyl interrupted by -0-, -S-, -NRa-, -0-C(=0)- or by -NRa-(C=O)- is, for example, a carboxy group esterified by C 3

-C

2 2 alkyl (defined hereinabove for R 1 ) interrupted by -0-, -S-, -NRa-, -0-C(=O)- or by -NRa-(C=O)-, e.g. 2-methoxyethoxy carbonyl, 2- or 3-methoxypropoxycarbonyl, 2-, 3- or 4-methoxybutoxycarbonyl, 2-ethoxyeth oxycarbonyl, 2- or 3-ethoxypropoxycarbonyl, 2-, 3- or 4-ethoxybutoxycarbonyl, 2-methylthio ethoxycarbonyl, 2- or 3-methylthiopropoxycarbonyl, 2-ethylthioethoxycarbonyl, WO 2004/026811 PCT/EP2003/010115 -7 2-dimethylaminoethoxycarbonyl, 2- or 3-dimethylaminopropoxycarbonyl, 2-diethylamino ethoxycarbonyl, 2- or 3-diethylaminopropoxycarbonyl, 2-acetoxyethoxycarbonyl or 2-(N acetoxy-N-methyl)-ethoxycarbonyl. X defined as carbamoyl of the partial formula A is, for example, carbamoyl, dimethyl- or di ethyl-carbamoyl. In addition, Rb and Re 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 -Caalkenylene, 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 0. In that case, the partial formula A corre sponds to a heterocyclylcarbonyl substituent, e.g. piperidinocarbonyl, piperazinylcarbonyl or morpholinocarbonyl. In the compounds (I) described hereinabove, the sum of the carbon atoms present in R 1 and X is preferably greater than ten. The definition used for Y*, "a salt-forming cation suitable for lubricant compositions", includes those cations of salt-formers that together with the carboxylate group form metal salts suit able 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. In a preferred embodiment of the invention, the definition used for 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,

(C

1

-C

2 2 alkyl) 14 ammonium or (2-hydroxyethyl) 14 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 lubricat ing viscosity, e.g. a lubricant, in a manner known per se. Component b) Base oil The definition "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. Tourret and E.P. Wright, Hy den & Son Ltd. GB, on behalf of The Institute of Petroleum London, ISBN 0 85501 317 6; WO 2004/026811 PCT/EP2003/010115 -8 Ullmann's Encyclopaedia of Ind. Chem., Fifth Completely Revised Edition, Verlag Chemie, DE-Weinheim, VCH-Publishers for U.S., Vol. A 15, page 423 ff (Lubricants), Vol. A 13, page 165 ff (Hydraulic Fluids). 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 exam ple 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-a-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, trimethylol propane 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 com plex esters of monovalent and divalent acids with polyhydric alcohols, for example a complex ester of trimethylolpropane with caprylic and sebacic acid, or a mixture thereof. Apart from mineral oils there are especially suitable, for example, poly-a-olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene glycols, and also mixtures thereof with water. 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 fre quently also emulsions of such substances in water or other liquids. The 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). The 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. Such addi- WO 2004/026811 PCT/EP2003/010115 -9 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. The following are examples of further additives: Phenolic antioxidants 1. 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-(a-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. 2,6-dinonyl 4-methylphenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)-phenol, 2,4-dimethyl-6-(1'-methyl heptadec-1'-yl)-phenol, 2,4-dimethyl-6-(1'-methyltridec-1'-yl)-phenol and mixtures thereof. 2. Alkylthiomethylphenols: 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6 methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol. 3. 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-hy droxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxy phenyl) adipate. 4. Tocopherols: a-, P-, y- or 8-tocopherols and mixtures thereof (vitamin E). 5. 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-methyl phenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulphide. 6. 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-(a-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-(a-methylbenzyl)-4 nonylphenol], 2,2'-methylenebis[6-(c,a-dimethylbenzyl)-4-nonylphenol], 4,4'-methylene bis(2,6-di-tert-butylphenol), 4,4'-methylenebis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert butyl-4-hydroxy-2-methylphenyl)butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4 methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl 4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3'-tert butyl-4'-hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-m ethyl phenyl)dicyclopentadiene, bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tert-butyl-4- WO 2004/026811 PCT/EP2003/010115 -10 methylphenyl] terephthalate, 1,1-bis(3,5-dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di tert-butyl-4-hydroxyphenyl)propane, 2,2-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n dodecylmercaptobutane, 1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane. 7. 0-, N- and S-benzyl compounds: 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzy 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-hydroxybenzy mercaptoacetate. 8. Hydroxybenzylated 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. 9. Hydroxvbenzyl 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. 10. Triazine compounds: 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-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-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6 tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hy droxyphenylpropionyl)hexahydro-1,3,5-triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxyben zyl) isocyanurate. 11. Acylaminophenols: 4-hydroxylauric acid anilide, 4-hydroxystearic acid anilide, N-(3,5-di tert-butyl-4-hydroxyphenyl)carbamic acid octyl ester. 12. 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-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-trioxabicy clo[2.2.2]octane. 13. 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-hexane- WO 2004/026811 PCT/EP2003/010115 - 11 diol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene gly col, 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-trioxabicyclo[2.2.2]oc tane. 14. Esters of beta-(3,5-dicyclohexyl-4-hydroxyphenl)propionic acid with mono- or poly-hy dric alcohols, e.g. with the alcohols mentioned under 13.. 15. Esters of 3,5-di-tert-butyl-4-hydroxvphenylacetic acid with mono- or poly-hydric alcohols, e.g. with the alcohols mentioned under 13.. 16. Amides of beta-(3,5-di-tert-butyl-4-hydroxyphenyl)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-hydroxy phenylpropionyl)hydrazine. Amine-type antioxidants N,N'-Di-isopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4 dimethylpentyl)-p-phenylenediamine, N,N'-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N'-bis(1 -methylheptyl)-p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N' diphenyl-p-phenylenediamine, N,N'-di(2-naphthyl)-p-phenylenediamine, N-isopropyl-N' phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-(1-me thylheptyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4-(p toluenesulphonamido)-diphenylamine, N,N'-dimethyl-N,N'-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthyl amine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octylated di phenylamine, for example p,p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyryl aminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylamino phenol, di(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-dia minodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N',N'-tetramethyl-4,4'-diaminodi phenylmethane, 1,2-di[(2-methylphenyl)amino]ethane, 1,2-di(phenylamino)propane, (o-tolyl) biguanide, di[4-(1',3'-dimethylbutyl)phenyl]amine, tert-octylated N-phenyl-1-naphthylamine, mixture of mono- and di-alkylated tert-butyl-/tert-octyl-diphenylamines, mixture of mono- and di-alkylated nonyldiphenylamines, mixture of mono- and di-alkylated dodecyldiphenylamines, mixture of mono- and di-alkylated isopropyl-/isohexyl-diphenylamines, mixtures of mono- and di-alkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phe nothiazine, mixture of mono- and di-alkylated tert-butyl-/tert-octyl-phenothiazines, mixture of mono- and di-alkylated tert-octylphenothiazines, N-allylphenothiazine, N,N,N',N'-tetraphenyl- WO 2004/026811 PCT/EP2003/010115 - 12 1,4-diaminobut-2-ene, N,N-bis(2,2,6,6-tetramethyl-piperidin-4-yl-hexamethylenediamine, bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 2,2,6,6-tetramethypiperidin-4-one, 2,2,6,6 tetramethylpiperidin-4-ol. Further antioxidants 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. Metal deactivators, for example for copper 1. 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. 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. 3. Imidazole derivatives: 4,4'-methylenebis(2-undecyl-5-methylimidazole); bis[(N-methyl) imidazol-2-yl]carbinol-octyl ether. 4. Sulphur-containinq 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. 5. Amino compounds: salicylidene-propylenediamine, salicylaminoguanidine and salts thereof. Rust inhibitors 1. Organic acids, their esters, metal salts, amine salts and anhydrides: alkyl- and alkenyl succinic acids and their partial esters with alcohols, diols or hydroxycarboxylic acids, par tial amides of alkyl- and alkenyl-succinic acids, 4-nonylphenoxyacetic acid, alkoxy- and alkoxyethoxy-carboxylic acids, such as dodecyloxyacetic acid, dodecyloxy(ethoxy)acetic acid and amine salts thereof, and also N-oleoyl-sarcosine, sorbitan monooleate, lead naphthenate, alkenylsuccinic acid anhydrides, e.g. dodecenylsuccinic acid anhydride, 2 (2-carboxyethyl)-1 -dodecyl-3-methylglycerol and salts thereof, especially sodium and triethanolamine salts thereof.

WO 2004/026811 PCT/EP2003/010115 - 13 2. Nitrogen-containing compounds: 2.1. 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. 2.2. Heterocyclic compounds, e.g. substituted imidazolines and oxazolines, e.g. 2-hepta decenyl-1 -(2-hydroxyethyl)-imidazoline. 3. Sulphur-containing compounds: barium dinonylnaphthalenesulphonates, calcium petroleum sulphonates, alkylthio-substituted aliphatic carboxylic acids, esters of aliphatic 2-sulphocarboxylic acids and salts thereof. Extreme-pressure and anti-wear additives 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-1 H-1,3-benzothia zole, derivatives of 2,5-dimercapto-1,3,4-thiadiazole such as 2,5-bis(tert-nonydithio)-1,3,4 thiadiazole. Friction coefficient reducing agents Lard oil, oleic acid, tallow, rapeseed oil, sulphurated fats, amines. Further examples are given in EP-A-0 565 487. Further additives 1. Viscosity index improvers: polyacrylates, polymethacrylates, vinylpyrrolidone/methacrylate copolymers, polyvinylpyrrolidones, polybutenes, olefin copolymers, styrene/acrylate co polymers, polyethers. 2. Pour-point depressants: poly(meth)acrylates, ethylene/vinyl acetate copolymer, alkyl polystyrenes, fumarate copolymers, alkylated naphthalene derivatives. 3. Dispersants/surfactants: polybutenylsuccinic acid amides or imides, polybutenylphos phonic acid derivatives, basic magnesium, calcium and barium sulphonates and phe nolates. Special additives For use in water/oil metal-working fluids and hydraulic fluids 1. Emulsifiers: petroleum sulphonates, amines, such as polyoxyethylated fatty amines, non ionic surface-active substances; WO 2004/026811 PCT/EP2003/010115 -14 2. Buffers: alkanolamines; 3. Biocides: triazines, thiazolinones, tris-nitromethane, morpholine, sodium pyridenethiol; 4. 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 com position 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 (1) 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 (1) wherein R 1 , R 2 , R 3 , X and Y are as defined. The following Examples illustrate the invention: Examples Temperatures are given in 0C; h: hour(s); min.: minutes; m.p.: melting point; drying in vacuo (1000C, about. 0.05 mbar) Synthesis Examples Example 1 N-(2-n-Butoxycarbonvlethyl)-N-(n-octadecyl)-succinic acid monoamide 0 0 n-octadecyl-NH 2 + Z O-(n-butyl)

-

H 0 0 o n-octadecyl, N" 0 -(n-butyl) 00 0 OH 1.1 14.1 g (0.110 mol) of acrylic acid n-butyl ester are added drop wise, at 600C, over the course of 10 min., to 28.4 g (0.100 mol) of n-octadecylamine and the clear reaction mixture is stirred at 1000 for 2 h; the cooled crude product is dissolved in 100 ml of WO 2004/026811 PCT/EP2003/010115 - 15 hexane, filtered and washed twice with 50 ml of water. The organic phase is concen trated by evaporation in a rotary evaporator, the residue is dried in vacuo and 40.0 g of a clear, colourless, medium-viscosity oil are obtained. 1.2 3.1 g (0.030 mol) of succinic anhydride are added to 11.9 g (0.030 mol) of the resulting intermediate product, and the clear reaction solution is stirred at 1000 for 1 h. The cooled crude product is dissolved in 100 ml of hexane, filtered and washed twice with 40 ml of water. The hexane solution is concentrated by evaporation in a rotary evapo rator and the residue is dried in vacuo. 13.7 g (92 % of theory) of a clear yellow oil, which crystallises on standing are obtained. M.p.: 50-52*C; elemental analysis: 70.24 % C (calc. 69.98), 10.91 % H (calc. 11.14), 2.80 % N (calc. 2.81). Example 2 N-(3-n-Butoxprropyl)-N-(2-n-dodecyloxvcarbonylethyl)-succinic acid monoamide 0 3-(n-butoxy)-propyl-NH 2 + OO-(n-dodeciT) N" 0-fl -(n-dodecyl) H ~O S 3-(n-butoxy)-propyk N 0-J -(n-dodecyl) 00 00 OH 2.1 26.7 g (0.10 mol) of acrylic acid n-dodecyl ester are added drop wise, over the course of 20 min., to 13.3 g (0.100 mol) of 3-n-butoxypropylamine and the reaction mixture is stirred at 1000 for 2 h; the cooled crude product is dried in vacuo and 37.0 g of a clear, colourless, low-viscosity oil are obtained. 2.2 4.2 g (0.040 mol) of succinic anhydride are added to 14.9 g (0.040 mol) of the resulting intermediate product and the reaction mixture is stirred for 2 h; the cooled crude prod uct is dissolved in 100 ml of hexane, filtered and washed three times with 30 ml of wa ter. The hexane solution is concentrated by evaporation in a rotary evaporator, the re maining product is dried in vacuo and 18.0 g (95 % of theory) of a clear yellow oil of medium viscosity are obtained. nD20 1.4670; elemental analysis: 66.85 % C (calc. 66.21), 10.54 % H (calc. 10.47), 2.72 % N (calc. 2.97).

WO 2004/026811 PCT/EP2003/010115 -16 noD 20 1.4670; elemental analysis: 66.85 % C (calc. 66.21), 10.54 % H (calc. 10.47), 2.72 % N (calc. 2.97). Example 3 N-(2-Morpholinocarbonylethyl)-N-(n-octadecyl)-succinic acid monoamide oleyl-NH 2 + Noey.s 00 0 oleyl, N'

-

N 0~ 00YN.~.%.k 0 H 3.1 5.8 g (0.040 mol) of 4-acryloylmorpholine are added drop wise, at 600, over the course of 10 min., to 10.7 g (0.040 mol) of oleylamine (Armeen@O), the reaction mixture is stirred at 1000 for 1 h and the cooled crude product is dried in vacuo. 16.0 g of a clear, light-yellow, low-viscosity oil are obtained. 3.2 4.1 g (0.040 mol) of succinic anhydride are added to 16 g (0.040 mol) of the resulting intermediate product, the reaction solution is stirred at 1000 for 1 h and the cooled crude product is shaken with 200 ml of hexane and 100 ml of brine (NaCI-saturated). The middle phase of the three phases is washed a further three times using 30 ml of brine each time and is dissolved in 100 ml of toluene, filtered and concentrated by evaporation in a rotary evaporator; the remaining product is dried in vacuo. 15.6 g (77 % of theory) of a clear yellow oil which becomes turbid on cooling are obtained. Elemental analysis: 68.24 % C (calc. 68.47), 10.23 % H (calc. 10.30), 5.34 % N (calc. 5.51). Example 4 The following compounds (1) can be prepared analogously to Examples 1-3: R~sN X R2()

R

3 O R 2 , R 3 , Y: H

OY

WO 2004/026811 PCT/EP2003/010115 -17 Table 1 Ex. R1 X Yield [% Appearance Analysis [found (cal of theory] culated)] 4.1 oleyl -C(=O)-O-(n-butyl) 99 clear, light-yellow, 70.79 % C (70.26) medium-viscosity 10.58 % H (10.78) oil no o 2 0 1.4761 2.82 % N (2.83) 4.2 oleyl -C(=O)-O-methyl 93 clear, yellow, vis- 69.97 % C (70.08) cous oil 10.40 % H (10.44) no 2 0 1.4804 3.10 % N (3.10) 4.3 oleyl -C(=O)-O(CH 2

)

2 -0-ethyl 96 clear, yellow, me- 69.02 % C (68.07) dium-viscosity oil 10.50 % H (10.44) nD 20 1.4768 2.77 % N (2.74) 4.4 oleyl -C(=O)-O-(isobutyl) 77 clear, yellow, me- 70.04 % C (70.26) dium-viscosity oil 10.76 % H (10.78) no2 1.4748 2.80 % N (2.83) 4.5 oleyl -C(=O)-O-ethyl 69 clear, yellow, me- 68.85 % C (69.34) dium-viscosity oil 10.50 % H (10.56) noo 20 1.4769 2.97 % N (2.99) 4.6 isotridecyl -C(=O)-O-(n-butyl) 90 clear, light-yellow, 67.56 % C (67.41) viscous oil 10.59 % H (10.61) nfo 1.4711 3.35 % N (3.28) 4.7 isotridecyl -C(=O)-O-(isobutyl) 87 clear, light-yellow, 67.63 % C (67.41) viscous oil 10.66 % H (10.61) no 1.4709 3.36 % N (3.28) 4.8 n-butyl -C(=O)-O-oleyl 95 clear, yellow, me- 70.80 % C (70.26) dium-viscosity oil 10.79 % H (10.78) noD 1.4752 2.56 % N (2.83) 4.9 n-dodecyl -C(=O)-O-ethyl 82 clear, light-yellow, 65.78 % C (65.42) medium-viscosity 10.39 % H (10.20) oil no 1.4706 3.72 % N (3.63) 4.10 oleyl Nitrile 87 clear, light-yellow, 72.13 % C (71.39) viscous oil 10.73 % H (10.54) no20 1.4783 6.23 % N (6.66) 4.11 n-octyl -C(=O)-O-oleyl 97 clear, yellow, vis- 72.04 % C (71.69) cous oil 11.05 % H (11.30) no20 1.4745 2.41 % N (2.53) 4.12 oleyl -C(=O)-O-(CH 2

)

2 0H 59 clear, light-yellow, 66.92 % C (67.05) viscous oil 9.99 % H (10.21) no 1.4855 2.86 % N (2.90) 4.13 oleyl -C(=O)-NH 2 82 clear, yellow, vis- 68.10 % C (68.45) cous oil 10.44 % H (10.57) no20 1.4745 6.26 % N (6.39) WO 2004/026811 PCT/EP2003/010115 - 18 Table 1 (ctd.) Ex. R1 X Yield [% Appearance Analysis [found (cal of theory] culated)] 4.14 coconut oil -C(=O)-O-(n-butyl) 87 clear, light-yellow, 67.68 % C (67.73) amine viscous oil 10.50 % H (10.18)

(C

1 2 mix) no 1.4701 3.31 % N (3.29) 4.15 n-butoxy-pro- -C(=O)-O-oleyl 97 clear, yellow, me- 69.75 % C (69.40) pyl dium-viscosity oil 10.66 % H (10.74) no 201.4744 2.40 % N (2.53) 4.16 Cs-C1oalkyl- -C(=O)-O-(n-butyl) 95 clear, yellow, me- 63.72 % C

O(CH

2 )3 dium-viscosity oil 10.00 % H nD 20 1.4680 3.19 % N 4.17 isodecyl- -C(=O)-O-(n-butyl) 96 clear, yellow, me- 64.75 % C (64.98)

O(CH

2

)

3 dium-viscosity oil 10.11 % H (10.22) nD20 1.4699 3.14 % N (3.16) 4.18 2-ethylhexyl -C(=O)-O-(n-dodecyl) 96 clear, light-yellow, 69.60 % C (69.04) medium-viscosity 10.69 % H (10.94) oil 2no 1,4684 2.67 % N (2.98) 4.19 methoxy- -C(=O)-O-(n-dodecyl) 98 wax-like solid 64.99 % C (64.31) propyl 10.14 % H (10.09) 2.91 % N (3.26) 4.20 C 8

-C

1 oalk- nitrile 97 clear, yellow, me- 63.62 % C (64.38)

O(CH

2 )s dium-viscosity oil 9.61 % H (9.67) nD20 1.4731 7.69 % N (7.90) 4.21 benzyl -C(=O)-O-(n-dodecyl) 97 wax-like solid 70.02 % C (69.77) 8.99 % H (9.23) 3.10 % N (3.13) 4.22 oleyl -C(=O)-O-cyclohexyl 98 clear, yellow, me- 71,35% C (71,36) dium-viscosity oil 10,12% H (10.62) nD20 1,4864 2,72% N (2,68) 4.23 oleyl -C(=O)-O-(CH 2

)

2 -0- 98 clear, yellow, me- 71,20% C (70,81) phenyl dium-viscosity oil 9,57% H (9,54) n 0 2 0 1,5025 2,43% N (2,50) 4.24 oleyl -C(=O)-O-(CH 2

)

2 -0- 94 clear, yellow, me- 67,82% C (67.43) methyl dium-viscosity oil 10,26% H (10.51) no 2 0 1,4791 2,85% N (2,81) 4.25 oleyl -C(=O)-O-(CH 2

)

2 -0- 94 clear, yellow, me- 66.55% C (67.54)

(CH

2

)

2 -O-ethyl dium-viscosity oil 10,55% H (10.34) nD 2 0 1,4771 2,51% N (2,52) 4.26 benzyl -C(=O)-O-dodecyl 98 yellowish, wax-like I __ I _ _ Isolid I WO 2004/026811 PCT/EP2003/010115 - 19 Table 1 (ctd.) 4.27 2-ethylhexyl -C(=O)-O-dodecyl 96 clear, yellow, me- 69,60% C (69,04) dium-viscosity oil 10,69% H (10,94) nD20 1,4684 2.67% N (2,98) 4.28 n-butyl -C(=O)-O-i-decyl 91 clear, yellow, me- 65,24% C (65,42) dium-viscosity oil 10,20% H (10,20) nD 1,4708 3,43% N (3,63) 4.29 methyl-O- -C(=O)-O-dodecyl 99 yellowish, wax-like 64,99% C (64,31)

(CH

2 )s solid 10,14% H (10,09) 2,91% N (3,26) 4.30 ethyl-O- -C(=O)-O-dodecyl 95 clear, yellow, me- 65.25% C (64.98)

(CH

2

)

3 dium-viscosity oil 10,28% H (10,22) nD20 1,4681 2,85% N (3,16) 4.31 ethyl-O- -C(=O)-O-oleyl 95 clear, yellowish, 69,09% C (68,53)

(CH

2 )a medium-viscosity 10,76% H (10,54) oil D20 1,4755 2,57% N (2.66) 4.32 i-propyl-O- -C(=O)-O-oleyl 96 clear, yellow, me- 68,19% C (68,98)

(CH

2

)

3 dium-viscosity oil 10,09% H (10,64) nD20 1,4741 2,55% N (2,59) 4.33 i-decyl-O- -C(=O)-O-n-butyl 96 clear, yellow, me- 64,75% C (64,98)

(CH

2

)

3 dium-viscosity oil 10,11% H (10,22) nD20 1,4699 3,14% N (3,16) 4.34 i-decyl-O- -C(=O)-O-i-butyl 95 clear, yellow, me- 64,87% C (64,98)

(CH

2 )s dium-viscosity oil 10,38% H (10,22) nD20 1,4696 3,25% N (3,16) 4.35 octadecyl-O- -C(=O)-O-i-butyl 96 clear, yellow, me- 66,76% C (67,30)

(CH

2

)

3 dium-viscosity oil 10,72% H (10,69) nD 20 1,4682 2,91% N (2.80) 4.36 oleyl -C(=O)-N(CH 2

)

5 94 clear, yellow, me- 70,76% C (71,10) dium-viscosity oil 10,98% H (10,74) nD20 1,4985 5,24% N (5,53) Application Examples Example 5 Testing of corrosion protection properties (of active ingredient-containing industrial, circulat ing, turbine and hydraulic oils) according to ASTM D 665 (= DIN 51585) 300 ml of formulated oil are mixed with 30 ml of synthetic seawater by stirring for 24 h at 600 whilst simultaneously immersing a steel round-section 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- WO 2004/026811 PCT/EP2003/010115 -20 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: no corrosion * 1: light corrosion (< 6 corrosion sites less than 1 mm in diameter) * 2: moderate corrosion (< 5 % of the surface corroded) * 3: heavy corrosion (> 5 % of the surface corroded) Example 6 Testing for filterability in the presence of calcium ions 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 700C (+/- 20C) 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 p Millipore® filter (type AAWP 04700) using compressed air at 1 bar (+/- 0.05 bar) positive pressure. The times re quired 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): Fl = (t3oomI - t200mi)/ 2 (tioomi - t5omi) Fl = 1 means that no resistance is built up at the filter. FI < 2 is the requirement for passing the test. In the event of the filter becoming blocked, a note is made after 60 min. of the volume of oil filtered up until then.

WO 2004/026811 PCT/EP2003/010115 - 21 Table 2 Example Degree of corrosion, Filterability in the pres according to ence of Ca 2 + ASTM D 665 Filtration index Fl Base formulation 3/3 1.25 1 1/0 2 0/0 1.20 3 0/0 1.25 4.1 0/0 1.13 4.2 0/0 1.11 4.3 0/0 1.05 4.4 1 / 1 1.05 4.5 0/1 1.1 4.6 1/0 4.7 0/0 4.8 0/0 1.05 4.9 0/0 4.10 0/0 1.05 4.11 1/1 4.12 1/1 4.13 1 /1 1.20 4.14 1/0 4.15 0/0 2505246-1 - 21A Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" or "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as, an acknowledgement or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.

Claims (9)

1. A composition comprising a) At least one compound of formula RR2 Rl* N ' o 3 0 0'Y' Wherein R 1 is a substituent selected from the group consisting of C-C2alkyI, C 2 -C 22 alkyl substituted by hydroxy, C 2 -C2alkyl interrupted by -C(=O)-, -O-C(=O)- or by -NR.-C(=O)-, C 3 -C2alkyl interrupted by -0-, -S-, -NRa-, -C(=O)-O- or by -C(=0)-NRa-, wherein R, denotes hydrogen or C-C2alkyl, phenyl, benzyl, 1- or

2-phenylethyl, 2-phenoxyethyl, furfuryl, 1-naphthyl, 1-naphthylmethyl, cyclo hexyl, cyclohexylmethyl and isobornyl; R 2 and R 3 are hydrogen, or one of R 2 and R 3 is hydrogen and the other is methyl; and X is carboxy or carboxylate and Y* is a salt-forming cation suitable for lubricant compositions; or X is derivatised carboxy selected from the group consisting of cyano, carboxy esterified by C-C2alkyl, carboxy esterified by hydroxy-C 2 -C2alkyl, carboxy es terified by C 2 -C 22 alkyl interrupted by -C(=0)-, -C(=0)-0- or by -C(=O)-NR.-, carboxy esterified by C 3 -C2alkyl interrupted by -0-, -S-, -NRa-, -0-C(=0)- or by -NR,-(C=0)-, wherein R. denotes hydrogen or C-C 22 alkyI, carboxy esterified by phenyl, benzyl, 1- or 2-phenylethyl, 2-phenoxyethyl, furfuryl, 1-naphthyl, 1 -naphthylmethyl, cyclohexyl, cyclohexylmethyl, isobornyl, and carbamoyl of the partial formula N-- R RA) WO 2004/026811 PCT/EP2003/010115 -23 Wherein Rb and R 0 are each independently of the other hydrogen, CrC 22 alkyl or 2-hydroxyethyl, or Rb and R, together are 0 2 -Calkylene, C 2 -C 8 alkenylene, C 2 -Cealkadienylene or 0 2 -C 8 alkylene, 0 2 -C 8 alkenylene or 0 2 -C 8 alkadienylene interrupted by -0- or by -NRa-, with Ra 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. 2. A composition according to claim 1, comprising a) At least one compound (1), wherein R 1 is a substituent selected from the group consisting of C-C 22 alkyl, C 2 -C 22 alkyl substituted by hydroxy, C 2 -C 22 alkyl interrupted by -C(=0)-, -0-C(=O)- or by -NRa-C(=O)-, C 3 -C 22 alkyl interrupted by -0-, -S-, -NRa-, -C(=0)-0- or by -C(=0)-NRa-, wherein Ra denotes hydrogen or C-C22alkyl, phenyl, benzyl, 1- or 2-phenylethyl, 2-phenoxyethyl, furfuryl, 1-naphthyl, 1-naphthylmethyl, cyclo hexyl, cyclohexylmethyl, and isobornyl; R 2 and R 3 are hydrogen, or one of R 2 and R 3 is hydrogen and the other is methyl; X is derivatised carboxy selected from the group consisting of cyano, carboxy esterified by C-C 22 alkyl, carboxy esterified by hydroxy-C 2 -C 22 alkyl, carboxy es terified by C 2 -C 22 alkyl interrupted by -C(=0)-, -C(=0)-0- or by -C(=0)-NRa-, car boxy esterified by C 3 -C 22 alkyl interrupted by -0-, -S-, -NRa-, -0-C(=0)- or by -NRa-(C=0)-, wherein Ra denotes hydrogen or C-C 22 alkyl, carboxy esterified by phenyl, benzyl, 1- or 2-phenylethyl, 2-phenoxyethyl, furfuryl, 1 -naphthyl, 1 -naphthylmethyl, cyclohexyl, cyclohexylmethyl, isobornyl, and carbamoyl of the partial formula (A), wherein Rb and Re are each independently of the other hy drogen, C-C 2 2 alkyl, or 2-hydroxyethyl, or Rb and R, together are 0 2 -Calkylene, 0 2 -C 8 alkenylene, 0 2 -C 8 alkadienylene or C 2 -Cealkylene, C 2 -C 8 alkenylene or 0 2 -C 8 alkadienylene interrupted by -0- or by -NRa-, with Ra 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.

3. A composition according to claim 1, comprising a) At least one compound (1), wherein WO 2004/026811 PCT/EP2003/010115 -24 R 1 is a substituent selected from the group consisting of C-C 22 alkyl, C 2 -C 22 alkyl interrupted by -C(=O)- or by -O-C(=O)-, C 3 -C 22 alkyl interrupted by -0-, -S- or by -C(=0)-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-C 2 2 alkyl, carboxy esterified by hydroxy-C 2 -C22alkyl, carboxy es terified by C 2 -C 22 alkyl interrupted by -C(=0)- or by -C(=0)-0-, carboxy esterified by C 3 -C 22 alkyl interrupted by -0-, -S- or by -0-C(=0)-, and carbamoyl of the partial formula (A) defined as heterocyclylcarbonyl; and Y* is a hydrogen ion, ammonium, (C-C 4 alkyl) 1 4ammonium or (2-hydroxy ethyl) 1 4ammonium; and b) A base oil of lubricating viscosity.

4. A composition according to claim 1, comprising a) At least one compound (1), wherein R 1 is a substituent selected from the group consisting of C-C 22 alkyl, C 3 -C 22 alkyl interrupted by -0-, 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-C 22 alkyl, carboxy esterified by C 3 -C 2 2 alkyl interrupted by -0-, and carbamoyl of the partial formula (A) defined as piperidinocarbonyl, piperaz inylcarbonyl or morpholinocarbonyl; and Y' is a hydrogen ion, ammonium, (C-C 4 alkyl) 1 .4ammonium or (2-hydroxyethyl) 1 . 4 ammonium; and b) A base oil of lubricating viscosity.

5. A composition according to claim 1, comprising a) At least one compound (1), wherein R 1 is a substituent selected from the group consisting of C-C 18 alkyl, C 3 -C 18 alkyl interrupted by -0-, phenyl and benzyl; R 2 and R 3 are hydrogen; X is carboxy and Y is ammonium, (C-C 4 alkyl) 1 .4ammonium or (2-hydroxyethyl) 1 .4 ammonium; or - 25 X is carboxylate or derivatised carboxy selected from the group consisting of cyano, carboxy esterified by C-C 1 salkyl, carboxy esterified by C 3 -C 18 alkyl inter rupted by -0-, and morpholinocarbamoyl; and Y is hydrogen, ammonium, (C-C 4 aIkyl) 1 .4ammonium or (2-hydroxyethyl)w 4 ammonium; and b) A base oil of lubricating viscosity.

6. A composition according to claim 1, comprising b) A base oil of lubricating viscosity which is used for hydraulic or metal-working fluids, greases, gear oils or engine oils.

7. A concentrate comprising at least one compound (1) wherein R 1 , R 2 , R 3 , X and Y are as defined in claim 1.

8. A method of improving the use properties of lubricants, which comprises adding toithe. lubricants at least one composition according to claim 1.

9. Compositions of claim 1, concentrates containing same and/or uses thereof substantially as herein described.