EP1173534B1 - Hydrauliköl - Google Patents

Hydrauliköl Download PDF

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Publication number
EP1173534B1
EP1173534B1 EP00917078.8A EP00917078A EP1173534B1 EP 1173534 B1 EP1173534 B1 EP 1173534B1 EP 00917078 A EP00917078 A EP 00917078A EP 1173534 B1 EP1173534 B1 EP 1173534B1
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EP
European Patent Office
Prior art keywords
carbon atoms
magnesium
salicylate
alkyl
hydraulic fluid
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.)
Expired - Lifetime
Application number
EP00917078.8A
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English (en)
French (fr)
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EP1173534A1 (de
Inventor
Andrew John Holmes
Cameron William Watson
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.)
Shell Internationale Research Maatschappij BV
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Shell Internationale Research Maatschappij BV
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Priority to EP00917078.8A priority Critical patent/EP1173534B1/de
Publication of EP1173534A1 publication Critical patent/EP1173534A1/de
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Publication of EP1173534B1 publication Critical patent/EP1173534B1/de
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
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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
    • C10M129/30—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
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    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
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    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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

Definitions

  • the present invention relates to a hydraulic fluid.
  • WO 93/03121 relates to hydraulic fluids having improved wet filterability and having increased resistance to loss of zinc when the oil is exposed to water.
  • These compositions comprise (A) a combination of a metal salt selected from the group consisting of sulfonates, phenates, carboxylates and mixtures thereof, (B) an aliphatic carboxylic acid or anhydride, or carboxylic acid group containing derivative thereof, wherein the aliphatic group contains at least 20 carbon atoms, and optionally (C) a metal salt of (C)(I) at least one organic phosphorus acid or mixture of (C)(I) at least one organic phosphorus acid and (C)(II) at least one carboxylic acid group, and optionally (D) triazole.
  • a metal salt selected from the group consisting of sulfonates, phenates, carboxylates and mixtures thereof
  • B an aliphatic carboxylic acid or anhydride, or carboxylic acid group containing derivative thereof, where
  • the carboxylic acids of (A) are aromatic carboxylic acids.
  • Zinc, calcium and magnesium salts of these aromatic carboxylic acids, and especially salicylic acids, are preferred.
  • magnesium salicylate and zinc dithiophosphate are both mentioned per se, there is no teaching to use the combination of these compounds.
  • WO 89/04358 relates to compositions comprising (A) a neutral or basic metal salt of an acidic organic compound, (B) a metal deactivator, preferably an optionally substituted benzotriazole, and (C) a sulfur and/or phosphorus-containing compound selected from the group consisting of (C-1) phosphorus-containing amide, (C-2) phosphorus-containing ester, (C-3) sulfur-coupled dithiocarbamate, (C-4) sulfur-containing compound according to formula (I).
  • Particularly preferred metals for the salts (A) are sodium, magnesium, calcium or mixtures of two or more thereof.
  • zinc dialkyl dithiophosphate is mentioned. Although magnesium salicylate and zinc dithiophosphate are both mentioned per se, there is no teaching to use the combination of these compounds.
  • EP-A-604 218 describes functional fluids comprising a major amount of an oil of lubricating viscosity, at least one metal salt of thiophosphoric acid, a zinc salt of salicylic acid, and a rust inhibitor, which fluid contains less than about 1 %wt of dispersant and less than about 1 %wt of basic sulfonate salt.
  • the thiophosphoric acid is most commonly a dihydrocarbyl dithiophosphoric acid; the metal is most preferably zinc.
  • the teaching of the document is restricted to the use of zinc salicylate.
  • Hydraulic fluids need to meet special requirements as they both lubricate and transmit pressure.
  • hydraulic fluids contain additives.
  • hydraulic fluids contain antiwear/extreme pressure additives.
  • the conditions for a hydraulic fluid are especially difficult in vane pumps where the vane tips slide against the casing at high speed under heavy load and at high temperature.
  • the increasingly high operating temperatures of modern hydraulic equipment requires the fluid to be thermally stable to avoid the formation of deposits and sludge and to resist the corrosion of both ferrous and non-ferrous metals.
  • the requirement of good thermal stability in hydraulic fluids containing an anti-wear additive means that these additives are often used in combination with detergents.
  • the calcium salts of alkylbenzene sulphonates, alkyl-naphthalene sulphonates, petroleum sulphonates, alkylphenates, alkyl sulphurized phenates or alkylsalicylates which are usually applied, give increased wear.
  • the increased wear is especially marked in vane pumps, more specifically under low load conditions. Low load conditions occur in practice when the pump is idle.
  • WO-A-97/10318 describes lubricants with improved acid neutralisation properties and excellent sludge and wear performance in the Seq. 5E test.
  • Said lubricants are formed using a detergent system comprising one or more alkali or alkaline earth metal salts of an oil soluble organic acid selected from the group consisting of sulfonic acids, phenols, sulfurised phenols and carboxylic acids (including salicylate acids) wherein at least one metal salt is overbased and the ratio of inorganic to organic salt present in the detergent system expressed as TBN from inorganic salts (the overbasing) to the total moles of organic salt is at least 2500.
  • a detergent system comprising one or more alkali or alkaline earth metal salts of an oil soluble organic acid selected from the group consisting of sulfonic acids, phenols, sulfurised phenols and carboxylic acids (including salicylate acids) wherein at least one metal salt is overbased and the ratio of inorganic to organic salt present in the detergent
  • US-A-5 558 802 states that neutral and overbased calcium salts of organic acids have been found to increase low temperature high shear viscosity when measured in a cold cranking simulator (CCS).
  • CCS cold cranking simulator
  • WO-A-96/37582 describes lubricating oil compositions for internal-combustion engines, automatic transmission gearboxes, dampers, power steering units and the like.
  • Lubricating oils of described in WO-A-96/37582 comprise sulfoxymolybdenum dithiocarbamate having a specific alkyl group, zinc dialkyl dithiophosphate having a specific alkyl group, specific alkylsalicylate(s), and, if desired, succinimide containing boron, each in a predetermined amount intra lubricating oil base stock.
  • US-A-4462918 describes a lubricating oil composition comprising a major proportion of a lubricating oil and a minor proportion of each of a Group II metal dithiophosphate and a composition having the formula: R 1 O.CO.CR 2 (NR 3 R 4 ).CR 6 R 7 CO.OR 5 , where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen or a hydrocarbon radical containing 1-30 carbon atoms, and wherein R 3 or R 4 are independently selected from hydrogen, hydrocarbon containing from 1 to 30 carbon atoms, and acyl containing from 1 to 30 carbon.
  • hydraulic fluid containing a combination of magnesium salicylate and zinc dithiophosphate gives improved performance at low load compared with a combination containing calcium salicylate. Additionally, it was found that this combination also provides greater thermal stability. Less sludge and deposits are formed when subjecting the hydraulic fluid of the present invention to the Cincinnati Milacron Thermal Stability Test.
  • the present invention provides a hydraulic fluid comprising a lubricant base oil in combination with (a) from 0.001 to 5 %wt of magnesium salicylate, (b) from 0.01 to 8 %wt of zinc dithiophosphate, and (c) from 0.001 to 5 %wt of a compound according to the following formula I in which R 1 and R 2 are each hydrogen or alkyl or hydroxyalkyl of 1 to 30 carbon atoms; R 3 , R 4 and R 5 are each hydrogen or alkyl or hydroxyalkyl of 1 to 4 carbon atoms; X is CH or N and R 6 and R 7 are each hydrogen, alkyl or alkenyl of 1 to 30 carbon atoms, or an acyl group derived from a saturated or unsaturated carboxylic acid of up to 30 carbon atoms.
  • the magnesium salicylate for use in the present invention can be either neutral or overbased.
  • the expression “overbased” is equivalent to “basic”, “superbased”, “hyperbased” and “high-metal containing salts”.
  • These magnesium salicylates contain an excess metal content compared to the amount of metal which would be present according to the stoichiometry of the metal and the salicylic acid reacted with the metal. Processes for making such neutral and basic metal salts are well known in the art.
  • Neutral salts can be made by heating a mineral oil solution of an acidic organic compound with a stoichiometric equivalent amount of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature above 50 °C and filtering the resulting mass.
  • a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide
  • Basic salts are made similarly with the exception that a stoichiometric excess of the metal is used.
  • overbased magnesium salicylate is used.
  • These compositions can be characterized by their total base number (TBN).
  • TBN total base number
  • the total base number is preferably at least 100 mg KOH/g, more preferably at least 200 mg KOH/g, most preferably at least 300 mg KOH/g.
  • the total base number is preferably at most 600 mg KOH/g.
  • Another method of characterising overbased magnesium salicylates is by the magnesium content relative to the stoichiometrically equivalent amount of magnesium based on the amount of total acid present.
  • Overbased magnesium salicyclates for use in the present invention preferably have a magnesium content of more than 500% of the stoichiometrically equivalent amount of magnesium based on the amount of total acid present, more preferably at least 550%.
  • the salicylate can be either substituted or unsubstituted. Suitable substituents include aliphatic groups containing from 1 to 40 carbon atoms and optionally containing one or more oxygen and/or nitrogen atoms, and hydroxy groups. Preferred substituents are alkyl groups containing from 6 to 30 carbon atoms, preferably from 12 to 20 carbon atoms. Preferably, the substituents are linear.
  • the salicylate can contain from 1 to 4 substituents, preferably from 1 to 3, most preferably 1 or 2 substituents. Most preferably, the salicylate is substituted by 1 linear alkyl group containing from 14 to 18 carbon atoms.
  • mono-alkyl salicylic acids are prepared by alkylation of phenol and subsequent carboxylation. Therefore, a small amount (generally at most 20 %mol) of dialkyl salicylate and unsubstituted salicylate can be present in the mono-alkyl salicylate.
  • Magnesium salicylate which can be used in the present invention, is commercially available.
  • a suitable commercial product is SAP 007 (ex Infineum).
  • SAP 007 Ex Infineum
  • the magnesium salicylate will usually be supplied in combination with mineral oil.
  • the amounts referred to in this document, relate to the compound per se without mineral oil.
  • Zinc dithiophosphate is well known in the art.
  • Preferred dithiophosphate for use in the present invention are represented by the following formula in which R 8 and R 9 can be either hydrogen or an aliphatic group.
  • the aliphatic group is preferably a hydrocarbyl group.
  • the hydrocarbyl group optionally contains an acid, a hydroxy and/or an ester group.
  • the hydrocarbyl group is preferably an alkyl containing up to 12 carbon atoms optionally further containing an acid, a hydroxy and/or an ester group.
  • the hydrocarbyl substituted dithiophosphate can contain 1 or 2 aliphatic groups, or it can be a mixture of dithiophosphates having 1 aliphatic group and dithiophosphates having 2 aliphatic groups.
  • the zinc dithiophosphate is a zinc dialkyl dithiophosphate.
  • Substituted dithiophosphates can contain primary, secondary and/or tertiary aliphatic substituents, i.e. substituents which are attached to the oxygen atom via a carbon atom attached to one, two or three further carbon atoms, respectively.
  • primary aliphatic substituents i.e. substituents which are attached to the oxygen atom via a carbon atom attached to one, two or three further carbon atoms, respectively.
  • Suitable zinc dithiophosphates which are commercially available include Elco 108 (ex Elco Corporation), Lz 1375 (ex Lubrizol), OLOA 4269Q (ex Oronite) and HITEC 680 (ex Ethyl).
  • the amount of magnesium salicylate which is present is preferably at most. 1 %wt, based on total composition, more preferably at most 0.5 %wt, most preferably at most 0.3 %wt.
  • the amount of magnesium salicylate which is present is preferably at least 0.001 %wt, more preferably at least 0.005 %wt more preferably at least 0.01 %wt, most preferably at least 0.015 %wt.
  • the amount of zinc dithiophosphate which is present is preferably at most 5 %wt, based on total composition, more preferably at most 3 %wt, most preferably at most 1 %wt.
  • the amount of zinc dithiophosphate which is present is preferably at least 0.05 %wt, more preferably at least 0.7 %wt, most preferably at least 0.1 %wt.
  • the hydraulic fluid further comprises (c) from 0.001 to 5 %wt of a rust inhibitor compound according to the following formula I in which R 1 and R 2 are each hydrogen or alkyl or hydroxyalkyl of 1 to 30 carbon atoms; R 3 , R 4 and R 5 are each hydrogen or alkyl or hydroxyalkyl of 1 to 4 carbon atoms; X is CH or N and R 6 and R 7 are each hydrogen, alkyl or alkenyl of 1 to 30 carbon atoms, or an acyl group derived from a saturated or unsaturated carboxylic acid of up to 30 carbon atoms.
  • a rust inhibitor compound according to the following formula I in which R 1 and R 2 are each hydrogen or alkyl or hydroxyalkyl of 1 to 30 carbon atoms; R 3 , R 4 and R 5 are each hydrogen or alkyl or hydroxyalkyl of 1 to 4 carbon atoms; X is CH or N and R 6 and R 7 are each hydrogen, alkyl or alkenyl of 1 to
  • R 1 and R 2 are each an alkyl of from 3 to 6 carbon atoms
  • R 3 , R 4 and R 5 are each hydrogen
  • X is N
  • R 6 and R 7 are each an alkyl of 15 to 20 carbon atoms or an acyl group derived from a saturated or unsaturated dicarboxylic acid containing 4 to 10 carbon atoms, at least one of R 6 and R 7 being an acyl group.
  • aspartic acid N-(3-carboxy-1-oxo-2-propenyl)-octadecyl-bis(2-methylpropyl)ester.
  • Such aspartic acid esters are commercially available. Processes for preparing such compounds having been described in EP-A-434 464 .
  • the hydraulic fluid comprises magnesium salicylate, zinc dithiophosphate and a rust inhibitor in such quantities that the weight ratio of magnesium salicylate to zinc dithiophosphate is from 1:5 to 1:100 and the weight ratio of magnesium salicylate to rust inhibitor is from 1:0 to 1:50.
  • the lubricant base oils present in the hydraulic fluid of the present invention can be any base fluid which is suitable for use in hydraulic fluids.
  • the base oil can be a natural or a synthetic lubricant base oil, or a mixture thereof.
  • the natural oil can be an animal oil or vegetable oil, such as lard oil or castor oil, or a mineral oil such as liquid petroleum oils and solvent treated or acid treated mineral lubricating oil of the paraffinic, naphthenic, or mixed paraffinic/naphthenic type which may be further refined by hydrocracking and hydrofinishing processes and/or dewaxing.
  • Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerised and interpolymerised olefins.
  • a suitable base oil contains poly-alpha-olefins, such as polydecene.
  • the base oil is a hydrocarbon base oil.
  • the base fluid is a mineral oil which contains less than 10 % by weight of aromatic compounds, preferably less than 5 % by weight, most preferably less than 3.0 % by weight, measured according to DIN 51378. It is further preferred that the base oil contains less than 1.0 %wt of sulphur, calculated as elemental sulphur, preferably less than 0.1 %wt, more preferably less than 0.05 %wt, measured according to ASTM D 4045.
  • Such mineral oils can be prepared by severe hydroprocessing.
  • the lubricating oil has a kinematic viscosity in the range of from 5 to 220 cSt at 40 °C, more preferably of from 10 to 200 cSt, most preferably of from 20 to 100 cSt.
  • the hydraulic fluid according to the present invention can contain further additives usually present in hydraulic fluids, such as pour point depressants, anti-foam agents and demulsifier.
  • Pour point depressants generally are high molecular weight polymers such as alkylaromatic polymers and polymethacrylates.
  • anti-foam agents silicone polymers and/or polymethacrylates are generally used.
  • Demulsifiers which are generally applied are polyalkylene glycol ethers.
  • detergents such as sulphonates and phenates, metal deactivators, antioxidants such as phenolic compounds, diphenyl amines and phenyl naphthyl amines, ashless anti-wear agents and/or ashless dispersants, such as succinimides, can be present.
  • the hydraulic fluids of the present invention contain magnesium salicylate.
  • the fluids contain a combination of magnesium and calcium salicylate.
  • the components of the present invention can be added per se to a lubricating oil, or they can be mixed into an additive package before being added to the lubricating oil.
  • the additive package for preparing the hydraulic fluid preferably contains magnesium salicylate, zinc dithiophosphate and a compound according to formula I, wherein the weight ratio of magnesium salicylate to zinc dithiophosphate is from 1:5 to 1:100 and the weight ratio of magnesium salicylate to the compound of formula I is from 1:0 to 1:50.
  • Zinc dithiophosphate zinc di(ethylhexyl)dithiophosphate (Elco 108 ex Elco corporation)
  • Compound according to formula I aspartic acid, N-(3-carboxy-1-oxo-2-propenyl)-N-octadecyl , bis(2-methylpropyl)ester.
  • compositions obtained are described in Table 1.
  • the amounts are of the compounds per se, excluding the mineral oil.
  • Compositions 1 and 2 were used in Vickers V104C vane pump tests. A new pump cartridge was used for each test. The test duration was 250 hours, performed at a fluid temperature of about 66 °C, at a fluid outlet pressure of 35 bar (3.5 MPa) and at a pump speed of 1450 revolutions per minute. The results are described in Table 1.
  • composition 1 Composition 2 magnesium salicylate 0.06 %wt - calcium salicylate - 0.06 %wt zinc dithiophosphate 0.37 %wt 0.37 %wt compound of formula I 0.10 %wt 0.10 %wt lubricant base oil balance balance Low load test ring weight loss (mg) 13 96 vane weight loss (mg) 2 1 total weight loss (mg) 15 97 From Table 1 it is clear that better protection against wear is provided by a composition containing magnesium salicylate (1), than by a composition containing calcium salicylate (2). The ring weight loss and total weight loss incurred when using composition 1 is significantly less than that incurred when composition 2 is employed. The vane weight loss is similar for both compositions.

Claims (2)

  1. Hydraulikflüssigkeit, umfassend ein Grundschmieröl in Kombination mit
    (a) 0,001 bis 5 Gew.-% Magnesiumsalicylat,
    (b) 0,01 bis 8 Gew.-% Zinkdithiophosphat und
    (c) 0,001 bis 5 Gew.-% einer Verbindung gemäß der folgenden Formel I
    Figure imgb0005
     in der R1 und R2 jeweils für Wasserstoff oder Alkyl oder Hydroxyalkyl mit 1 bis 30 Kohlenstoffatomen stehen; R3, R4 und R5 jeweils für Wasserstoff oder Alkyl oder Hydroxyalkyl mit 1 bis 4 Kohlenstoffatomen stehen; X für CH oder N steht und R6 und R7 jeweils für Wasserstoff, Alkyl oder Alkenyl mit 1 bis 30 Kohlenstoffatomen oder eine Acylgruppe, die sich von einer gesättigten oder ungesättigten Carbonsäure mit bis zu 30 Kohlenstoffatomen ableitet, steht.
  2. Hydraulikflüssigkeit nach Anspruch 1, wobei die Flüssigkeit ferner Pourpoint-Erniedriger, Antischaummittel und/oder Demulgator umfasst.
EP00917078.8A 1999-04-14 2000-04-11 Hydrauliköl Expired - Lifetime EP1173534B1 (de)

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EP99302883 1999-04-14
EP99302883 1999-04-14
PCT/EP2000/003258 WO2000063325A1 (en) 1999-04-14 2000-04-11 Hydraulic fluid
EP00917078.8A EP1173534B1 (de) 1999-04-14 2000-04-11 Hydrauliköl

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GB0011115D0 (en) * 2000-05-09 2000-06-28 Infineum Int Ltd Lubricating oil compositions
US7563751B2 (en) 2002-08-05 2009-07-21 Nippon Oil Corporation Lubricating oil composition
US20080139430A1 (en) * 2006-12-08 2008-06-12 Lam William Y Additives and lubricant formulations for improved antiwear properties
US20100029525A1 (en) 2008-07-31 2010-02-04 Chevron Oronite Company Llc Antiwear hydraulic fluid composition with useful emulsifying and rust prevention properties
JP5875952B2 (ja) * 2012-07-12 2016-03-02 コスモ石油ルブリカンツ株式会社 農業機械用潤滑油組成物
JP6714503B2 (ja) * 2016-12-28 2020-06-24 シェルルブリカンツジャパン株式会社 電子制御機器を配した油圧作動機用潤滑油組成物
JP2023521642A (ja) * 2020-03-30 2023-05-25 中国石油化工股▲ふん▼有限公司 燃料潤滑性改良剤およびその応用
CN115537242B (zh) * 2021-06-30 2023-11-10 中国石油化工股份有限公司 柴油抗磨剂组合物、其制备方法及柴油组合物

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US4627928A (en) * 1976-08-26 1986-12-09 The Lubrizol Corporation Basic non-carbonated magnesium compositions and fuel, lubricant and additive concentrate compositions containing same
GB2115000B (en) * 1982-02-17 1985-02-06 Shell Int Research Lubricating oils and hydraulic fluids
GB8929096D0 (en) * 1989-12-22 1990-02-28 Ethyl Petroleum Additives Ltd Metal free lubricants
DE69202849T2 (de) * 1991-05-01 1995-10-26 Lubrizol Corp Thermisch stabile Zusammensetzungen und diese enthaltende Schmiermitteln und funktionelle Flüssigkeiten.
CA2086970A1 (en) * 1992-01-24 1993-07-25 Michelle M. Cervenka Low ash lubricating oil compositions
JP3151784B2 (ja) * 1992-05-01 2001-04-03 出光興産株式会社 耐熱作動油組成物
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US5558802A (en) * 1995-09-14 1996-09-24 Exxon Chemical Patents Inc Multigrade crankcase lubricants with low temperature pumpability and low volatility

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AU762520B2 (en) 2003-06-26
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ZA200108402B (en) 2002-12-24
CA2370468A1 (en) 2000-10-26
CN1229477C (zh) 2005-11-30
WO2000063325A1 (en) 2000-10-26
KR100697579B1 (ko) 2007-03-22
JP2002542378A (ja) 2002-12-10
CA2370468C (en) 2008-01-15
AU3820300A (en) 2000-11-02
KR20020010602A (ko) 2002-02-04
CN1349556A (zh) 2002-05-15
BR0009738B1 (pt) 2011-01-25

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