EP1385926A1 - Composition d'huile lubrifiante comprenant une combinaison d'addition composee d'un acide carboxylique et d'une amine en tant qu'agent antirouille - Google Patents
Composition d'huile lubrifiante comprenant une combinaison d'addition composee d'un acide carboxylique et d'une amine en tant qu'agent antirouilleInfo
- Publication number
- EP1385926A1 EP1385926A1 EP02745288A EP02745288A EP1385926A1 EP 1385926 A1 EP1385926 A1 EP 1385926A1 EP 02745288 A EP02745288 A EP 02745288A EP 02745288 A EP02745288 A EP 02745288A EP 1385926 A1 EP1385926 A1 EP 1385926A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- lubricating oil
- oil composition
- carboxylic acid
- weight
- composition according
- 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.)
- Granted
Links
Classifications
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- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/30—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
- C10M129/36—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms containing hydroxy groups
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- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
- C10M129/40—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms monocarboxylic
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- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/56—Acids of unknown or incompletely defined constitution
- C10M129/58—Naphthenic acids
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- C10M129/76—Esters containing free hydroxy or carboxyl groups
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- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M135/26—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
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- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- the present invention relates to a lubricating oil composition which has excellent anti-rust properties in severe operating environments in which water or seawater is admixed, and which also exhibits excellent properties 5 in terms of both the lubricating properties and anti- corrosion properties in various types of machinery.
- Anti-rust agents are added to lubricating oils to protect the mechanical parts from rusting when water or seawater is admixed. In general, anti-rust agents are
- the present invention provides a lubricating oil composition comprising a minor amount of an additive combination comprising
- R 1 represents a saturated or unsaturated alkyl group which has from 12 to 30 carbon atoms, and n is an integer of value 1 or 2;
- N-alkylpolyalkylenediamines which can be represented by general formula (2) ,
- R 2 represents a saturated or unsaturated alkyl group which has from 12 to 30 carbon atoms, and m is an integer of value from 2 to 5; and a major amount of a lubricating oil base oil .
- major amount in the present invention is meant at least 50 wt . %, with respect to the total weight of the lubricating oil composition.
- Said composition generally comprises from 0.001 to 0.5 part by weight of the carboxylic acid-based or carboxylic acid ester-based anti-rust agent; and from 0.001 to 0.2 part by weight of the at least one type of amine, per 100 parts by weight of lubricating oil base oil .
- said composition comprises from 0.001 to
- said composition comprises from 0.005 to 0.05 part by weight of said anti-rust agent, per 100 parts by weight of lubricating oil base oil.
- .said composition comprises from 0.001 to 0.05 part by weight of the at least one type of amine, per 100 parts by weight of lubricating oil base oil.
- the lubricating oil composition comprises, as an extreme pressure additive, a ⁇ -dithiophosphbrylpropionic acid which can be represented by general formula (3) ,
- R 3 represents a branched alkyl group which has from 3 to 8 carbon atoms
- R 4 is a hydrogen atom or a group selected from among the linear chain or branched alkyl groups which have from 1 to 4 carbon atoms .
- Said extreme pressure additive of formula (3) is preferably present in an amount in the range of from
- Ph represents a phenyl group
- R 5 is a hydrogen atom or a linear chain or branched alkyl group which has from 1 to 9 carbon atoms .
- Said extreme pressure additive of formula (4) is preferably present in an amount in the range of from 0.05 to 5 parts by weight, more preferably from 0.05 to 0.5 part by weight, per 100 parts by weight of lubricating oil base oil .
- the lubricating oil composition comprises, as an extreme pressure additive, an acidic phosphate ester which can be represented by general formula (5) ,
- R 6 is a linear chain or branched alkyl group which has from 3 to 13 carbon atoms, and r is an integer of value 1 or 2.
- Said extreme pressure additive of formula (5) is preferably present in an amount in the range of from 0.01 to 0.5 part by weight, more preferably from 0.01 to 0.1 part by weight, per 100 parts by weight of lubricating oil base oil . > 4
- the lubricating oil composition of the present invention may optionally comprise one or more of compounds of formulae (3) to (5) as extreme pressure additives.
- the lubricating oil base oil from which the lubricating oil composition of the present invention is constituted is not subject to any particular limitation, provided that it comprises petroleum-based oil and/or synthetic hydrocarbon-based oil.
- Lubricating oil base oils having a kinematic viscosity of from 2 to 680 mm 2 /s (40°C) , preferably of from 5 to 320 mm 2 /s (40°C) , and most preferably of from 8 to 220 mm 2 /s (40°C) ; a total sulphur content (wt. %) of from 0 to 1 wt . % , and preferably of from 0 to 0.3 wt . % ; a total nitrogen content (wt. ppm) of from 0 to 100 ppm, and preferably of from 0 to 30 ppm; and an aniline point of from 80 to 130°C, and preferably of from 100 to 125°C, are preferred.
- the petroleum-based lubricating oil base oils which can be used in the present invention may be, for example, individual solvent refined base oils, hydrogenation refined base oils or highly hydrogenated and cracked base oils, or mixtures of such oils.
- Highly hydrogenated cracked base oils are lubricating oil base oils which have a viscosity index of at least 130 (typically from 145 to 155) obtained with a slack wax which has been cracked and solvent de-waxed as the raw material by isomerizing the linear chain paraffins to branched paraffins by hydrogenation cracking in the presence of a catalyst (contact cracking) , or lubricating base oils which have a viscosity index of at least 130 (typically from 145 to 155) obtained using heavy linear chain paraffins which have been obtained by Fischer-Tropsch polymerization using the carbon monoxide and hydrogen obtained by a gasification process (partial oxidation) of a natural gas (such as methane) and subjecting this to catalytic cracking and isomerization in the same way
- the synthetic hydrocarbo -based base oils which may be used in the present invention include the olefin oligomers obtained by the homopolymerization or copolymerization of monomers which have been selected from among the linear chain and branched olefinic hydrocarbons which have from 3 to 15 carbon atoms, and preferably from 4 to 12 carbon atoms .
- the petroleum based lubricating oil base oils and synthetic hydrocarbon based base oils can be used individually or in the form of mixtures .
- the carboxylic acid based or carboxylic acid ester- based anti-rust agents which can be used in the present invention have a carboxylic acid or carboxylic acid ester group in the anti-rust agent molecule and they are widely used generally in lubricating oils .
- Said anti-rust agents include, for example, monocarboxylic acids which have from 8 to 30 carbon atoms, alkyl or alkenyl succinates or partial esters thereof, hydroxy-fatty acids which have from 12 to 30 carbon atoms and derivatives thereof, sarcosines which have from 8 to 24 carbon atoms and derivatives thereof, amino acids and derivatives thereof, naphthenic acid and derivatives thereof, lanolin fatty acid, mercapto-fatty acids and paraffin oxides.
- anti-rust agents are indicated below.
- Caprylic acid pelargonic acid, decanoic acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid, cerotic acid, montanic acid, melissic acid, oleic acid, docosanic acid, erucic acid, eicosenic acid, beef tallow fatty acid, soy bean fatty acid, coconut oil fatty acid, linolic acid, linoleic acid, tall oil fatty acid, 12- hydroxystearic acid, laurylsarcosinic acid, myritsylsarcosinic acid, palmitylsarcosinic acid, stearylsarcosinic acid, oleylsarcosinic acid, alkylated (C8 - C20) phenoxyacetic acids, lanolin fatty acid and C8 - C24 mercapto-fatty acids.
- R 7 and R 8 each independently represent hydrogen or a group selected from among the Cl to C30 alkyl groups, the Cl to C30 acyl groups and the alkyloxide groups, and R 9 to R 13 each independently represent hydrogen or a group selected from among the Cl to C30 alkyl groups .
- Examples of the aforementioned alkylamines represented by general formula (1) include primary amines such as laurylamine, coconut-amine, n-tridecylamine, myristylamine, n-pentadecylamine, palmitylamine, n- heptadecylamine, stearylamine, n-nonadecylamine, n-eicosylamine, n-heneicosylamine, n-docosylamine, n- tricosylamine, n-pentacosylamine, oleylamine, beef tallow-amine, hydrogenated beef tallow-amine and soy bean-amine.
- primary amines such as laurylamine, coconut-amine, n-tridecylamine, myristylamine, n-pentadecylamine, palmitylamine, n- heptadecylamine, stearylamine, n-nonadecylamine,
- secondary amines examples include dilaurylamine, di-coconut-amine, di-n-tridecylamine, dimyristylamine, di-n-pentadecylamine, dipalmitylamine, di-n-pentadecylamine, distearylamine, di-n- nonadecylamine, di-n-eicosylamine, di-n-heneicosylamine, di-n-docosylamine, di-n-tricosylamine, di-n-pentacosyl- amine, dioleylamine, di-beef tallow-amine, di- hydrogenated beef tallow-amine and di-soy bean-amine.
- N- alkylpolyalkyenediamines which can be represented by general formula (2) include ethylenediamines such as laurylethylenediamine, coconut ethylenediamine, n- tridecylethylenediamine, myristylethylenediamine, n- pentadecylethylenediamine, palmitylethylenediamine, n- heptadecylethylenediamine, stearylethylenediamine, n- nonadecylethylenediamine, n-eicosylethylenediamine, n- heneicosylethylenediamine, n-docosylethylendiamine, n- tricosylethylenediamine, n-pentacosylethylenediamine, oleylethylenediamine, beef tallow-ethylenediamine, hydrogenated beef tallow-ethylenediamine and soy bean- ethylenediamine; propylenediamines such as laurylpropylpropyl,
- supplementary additives of the various types which are generally used can be added to the lubricating oil composition of the present invention, as required, in order to further improve the performance thereof .
- Supplementary additives that may be added to the lubricating oil composition of the present invention include the known lubricating oil additives such as antioxidants, metal deactivators, extreme pressure additives, antifoa ing agents, viscosity index increasing agents, flow-point reducing agents, cleaning and dispersing agents, anti-rust agents and anti- emulsification agents.
- amine-based antioxidants examples include dialkyldiphenylamines such as p,p' -dioctyldiphenylamine (manuf ctured by the Seiko Kagaku Co . under the trade designation "Nonflex OD-3"), p,p'-di- ⁇ - methylbenzyldiphenylamine and N-p-butylphenyl-N-p' - octylphenylamin ; monoalkyldiphenylamines such as mono-t- butyldiphenylamine, and monooctyldiphenylamine; bis (dialkylphenyl) amines such as di(2,4- diethylphenyl) amine and di (2-ethyl-4-nonylphenyl) amine; alkylphenyl-1-naphthylamines such as octylphenyl-1- naphthylamine and N-t-dodecy
- sulphur-based antioxidants include dialkylsulphides such as didodecylsulphide and dioctadecylsulphide; thiodipropionic acid esters such as didodecyl thiodipropionate, dioctadecyl thiodipropionate, dimyristyl thiodipropionate and dodecyloctadecyl thiodipropionate, and 2-mercaptobenzimidazole.
- phenol-based antioxidants examples include 2-t- butylphenol, 2-t-butyl-4-methylphenol, 2-t-butyl-5- methylphenol , 2, 4-di-t-butylphenol, 2 ,4-dimethyl-6-t- butylphenol, 2-t-butyl-4-methoxyphenol, 3-t-butyl-4- methoxyphenol, 2, 5-di-t-butylhydroquinone (manufactured by the Kawaguchi Kagaku Co.
- Antage DBH 2 , 6-di-t-butylphenol and 2 , 6-di-t-butyl-4- alkylphenols such as 2, 6-di-t-butyl-4-methylphenol and 2, 6-di-t-butyl-4-ethylphenol; 2, 6-di-t-butyl-4- alkoxyphenols such as 2, 6-di-t-butyl-4-methoxyphenol and 2 , 6-di-t-butyl-4-ethoxyphenol, 3 , 5-di-t-butyl-4- hydroxybenzylmercaptooctyl acetate, alkyl-3- (3, 5-di-t- butyl-4-hydroxyphenyl)propionates such as n-octyl-3- (3 , 5- di-t-butyl-4-hydroxyphenyl) propionate (manufactured by the Yoshitomi Seiyaku Co.
- Yonox SS n-dodecyl-3- (3 , 5-di-t-butyl-4- hydroxyphenyl) propionate and 2 ' -ethylhexyl-3- (3 , 5-di-t- butyl-4-hydroxyphenyl) propionate; 2, 6-di-t-butyl- ⁇ - dimethylamino-p-cresol, 2, 2 ' -methylenebis (4-alkyl-6-t- butylphenol) compounds such as 2, 2 ' -methylenebis (4- methyl-6-t-butylphenol) (manufactured by the Kawaguchi Kagaku Co.
- phosphorus-based antioxidants include triaryl phosphites such as triphenyl phosphite and tricresyl phosphite, trialkyl phosphites such as trioctadecyl phosphite and tridecyl phosphite, and tridodecyl trithiophosphite .
- antioxidants can be used individually or in the form of mixtures, conveniently in amounts within the range of from 0.01 to 2.0 parts by weight, per 100 parts by weight of base oil .
- the metal deactivating agents which can be used in the lubricating oil a composition of the present invention include benzotriazole and the
- 4-alkylbenzotriazoles such as 4-methylbenzotriazole and 4-ethylbenzotriazole; 5-alkylbenzotriazoles such as 5- methylbenzotriazole, 5-ethylbenzotriazole; 1- alkylbenzotriazoles such as l-dioctylaminomethyl-2, 3- benzotriazole; benzotriazole derivatives such as the 1- alkyltolutriazoles, for example, 1-dioctylaminomethyl- 2, 3-tolutriazole; benzimidazole and benzimidazole derivatives such as 2- (alkyldithio) -benzimidazoles, for example, such as 2- (octyldithio) -benzimidazole, 2- (decyldithio) benzimidazole and 2- (dodecyldithio) - benzimidazole; 2- (alkyldithio) -toluimid
- 2- (alkyldithio) toluoxazoles such as 2- (octyldithio) toluoxazole, 2- (decyldithio) toluoxazole, 2- (dodecyldithio) toluoxazole; 2 , 5-bis (alkyldithio) -1, 3 , 4- thiadiazoles such as 2, 5-bis (heptyldithio) -1, 3 ,4- thiadiazole, 2 , 5-bis- (nonyldithio) -1, 3 , 4-thiadiazole, 2, 5-bis (dodecyldithio) -1, 3, 4-thiadiazole and 2,5-bis- (octadecyldithio) -1,3, 4-thiadiazole; 2, 5-bis (N,N-dialkyl- dithiocarbamyl) -1, 3 , 4-thiadiazole;
- metal deactivating agents can be used individually or in the form of mixtures, conveniently in an amount within the range of from 0.01 to 0.5 parts by weight, per 100 parts by weight of base oil.
- the materials which can be used as anti-foaming agents include, for example, dimethylpolysiloxane, organosilicates such as diethylsilicate, the fluorosilicones, and non-silicone based anti-foaming agents such as poly (alkylene acrylate) . These can be added and used individually or in the form of mixtures, conveniently in an amount of from 0.0001 to 0.1 part by weight, per 100 parts by weight of base oil.
- the viscosity index increasing agents which can be used include, for example, polymethacrylates and ethylene/propylene copolymers, other non-dispersion type viscosity index increasing agents such as olefin copolymers like styrene/diene copolymers, and dispersible type viscosity index increasing agents where a nitrogen containing monomer has been copolymerized in such materials. These materials can be added and used individually or in the form of mixtures, conveniently in an amount within the range of from 0.05 to 20 parts by weight per 100 parts by weight of base oil.
- flow-point reducing agents examples include polymethacrylate based polymers. These materials can be added and conveniently used in an amount within the range from 0.01 to 5 parts by weight per 100 parts by weight of base oil.
- cleaning and dispersing agents examples include metal-based detergents such as the neutral and basic alkaline earth metal sulphonates, alkaline earth metal phenates and alkaline earth metal salicylates alkenylsuccinimide and alkenylsuccinimide esters and their borohydrides , and ashless dispersing agents which have been modified with sulphur compounds. These agents can be added and used individually or in the form of mixtures, conveniently in an amount within the range of from 0.01 to 1 part by weight per 100 parts by weight of base oil .
- extreme pressure additives include sulphur-based extreme pressure additives such as dialkyl sulphides, dibenzyl sulphide, dialkyl polysulphides , dibenzyl disulphide, alkyl mercaptans, dibenzothiophene and 2, 2 ' -dithiobis (benzothiazole) ; phosphorus-based extreme pressure additives such as trialkyl phosphates, triaryl phosphates, trialkyl phosphonates, trialkyl phosphites, triaryl phosphites and dialkylhydrozine phosphites, and phosphorus- and sulphur-based extreme pressure additives such as zinc dialkyldithiophosphates, dialkylthiophosphoric acid, trialkyl thiophosphate esters, acidic thiophosphate esters and trialkyl trlthiophosphates .
- sulphur-based extreme pressure additives such as dialkyl sulphides, dibenzyl
- extreme pressure additives can be used individually or in the form of mixtures, conveniently in an amount within the range from 0.1 to 2 parts by weight, per 100 parts by weight of the base oil.
- the known anti-emulsifying agents which are generally used as lubricating oil additives can also be used. These agents may be conveniently added and used in an amount within the range from 0.0005 to 0.5 part by weight, per 100 parts by weight of the base oil.
- anti-emulsifying agents include polyalkylene glycol-based non-ionic surfactants, for example, polyoxyethylenealkyl ethers, polyoxyethylene alkylphenyl ethers and polyoxyethylene alkylnaphthyl ethers.
- the lubricating oil composition of the present ivnention is useful as a hydraulic oil composition, a compressor oil composition, a turbine oil composition, a bearing oil composition and/or a gear oil composition.
- the present invention will now be described with reference to the following Examples which are not intended to limit the scope of the present invention in any way. Illustrative Examples
- Sample oils were prepared by compounding extreme pressure additives and carboxylic acid based and carboxylic acid ester-based anti-rust agents and amines at various concentrations as shown in Table 1 in a hydrogenation refined base oil of kinematic viscosity
- compositions and test results are shown in Tables 1 to 3.
- Lubrizol 859 1. manufactured by the Lubrizol Co under the trade designation "Lubrizol 859" .
- Comparative Example 1 had only the extreme pressure additive compounded therein. Whilst said example and exhibited good extreme pressure performance in the gear wheel test, rust formed in the anti-rust test as no anti- rust agent and amine had been added thereto.
- the lubricating oil compositions of the present invention are virtually free, or completely free, of metals which are harmful in respect of both the environment and safety and they maintain a good anti-rust performance whilst also having good extreme pressure performance to match the increased speeds, higher pressures, more compact nature and improvement in durability requirements of modern industrial machinery.
- the amount of anti-rust agent added can be reduced by means of the present invention and lubricating oil compositions which have excellent performance can be provided more cheaply.
- the lubricating oil compositions of the present invention are useful as lubricating oil compositions where both anti-rust performance and extreme pressure performance are required and they can be used as hydraulic working oils, gear wheel oils, compressor oils, turbine oils and bearing oils .
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- Chemical & Material Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
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Applications Claiming Priority (3)
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JP2001142228 | 2001-05-11 | ||
JP2001142228A JP4608129B2 (ja) | 2001-05-11 | 2001-05-11 | 潤滑油組成物 |
PCT/EP2002/005066 WO2002092735A1 (fr) | 2001-05-11 | 2002-05-07 | Composition d'huile lubrifiante comprenant une combinaison d'addition composee d'un acide carboxylique et d'une amine en tant qu'agent antirouille |
Publications (2)
Publication Number | Publication Date |
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EP1385926A1 true EP1385926A1 (fr) | 2004-02-04 |
EP1385926B1 EP1385926B1 (fr) | 2006-03-01 |
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EP02745288A Expired - Lifetime EP1385926B1 (fr) | 2001-05-11 | 2002-05-07 | Composition d'huile lubrifiante comprenant une combinaison d'addition composee d'un acide carboxylique et d'une amine en tant qu'agent antirouille |
Country Status (11)
Country | Link |
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US (1) | US20040214733A1 (fr) |
EP (1) | EP1385926B1 (fr) |
JP (1) | JP4608129B2 (fr) |
KR (1) | KR100866811B1 (fr) |
CN (1) | CN1325620C (fr) |
AT (1) | ATE318881T1 (fr) |
CA (1) | CA2447044A1 (fr) |
DE (1) | DE60209497T2 (fr) |
DK (1) | DK1385926T3 (fr) |
ES (1) | ES2259375T3 (fr) |
WO (1) | WO2002092735A1 (fr) |
Cited By (1)
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US9453178B2 (en) | 2011-07-25 | 2016-09-27 | David McCreery | Corrosion-inhibiting lubricant and methods therefor |
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- 2002-05-07 CN CNB028097017A patent/CN1325620C/zh not_active Expired - Lifetime
- 2002-05-07 AT AT02745288T patent/ATE318881T1/de not_active IP Right Cessation
- 2002-05-07 ES ES02745288T patent/ES2259375T3/es not_active Expired - Lifetime
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US9453178B2 (en) | 2011-07-25 | 2016-09-27 | David McCreery | Corrosion-inhibiting lubricant and methods therefor |
Also Published As
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ATE318881T1 (de) | 2006-03-15 |
CN1325620C (zh) | 2007-07-11 |
DK1385926T3 (da) | 2006-07-10 |
JP4608129B2 (ja) | 2011-01-05 |
EP1385926B1 (fr) | 2006-03-01 |
JP2002338983A (ja) | 2002-11-27 |
DE60209497D1 (de) | 2006-04-27 |
KR20030096370A (ko) | 2003-12-24 |
CA2447044A1 (fr) | 2002-11-21 |
WO2002092735A1 (fr) | 2002-11-21 |
CN1522295A (zh) | 2004-08-18 |
ES2259375T3 (es) | 2006-10-01 |
US20040214733A1 (en) | 2004-10-28 |
KR100866811B1 (ko) | 2008-11-04 |
DE60209497T2 (de) | 2006-11-16 |
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