EP1786888A1 - Composes heterocycliques contenant de l'azote utilises comme additif dans des carburants pour reduire l'usure de contact - Google Patents

Composes heterocycliques contenant de l'azote utilises comme additif dans des carburants pour reduire l'usure de contact

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Publication number
EP1786888A1
EP1786888A1 EP05783500A EP05783500A EP1786888A1 EP 1786888 A1 EP1786888 A1 EP 1786888A1 EP 05783500 A EP05783500 A EP 05783500A EP 05783500 A EP05783500 A EP 05783500A EP 1786888 A1 EP1786888 A1 EP 1786888A1
Authority
EP
European Patent Office
Prior art keywords
fuel
additive
compound
use according
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05783500A
Other languages
German (de)
English (en)
Inventor
Ludwig Völkel
Arno Lange
Christian Lockemann
Dietmar Posselt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1786888A1 publication Critical patent/EP1786888A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines

Definitions

  • Nitrogen-containing heterocyclic compounds as Reibverschl formulate-reducing additive to fuels
  • the present invention relates to the use of at least one heterocyclic compound of the formula (I)
  • R is H, or C 1 -C 3 -AIRyI, as a scuffing-reducing additive in fuel compositions; correspondingly additized fuel compositions and their preparation; and additive concentrates comprising such compounds.
  • Carburettors and intake systems of gasoline engines are heavily contaminated by impurities caused by dust particles from the air, unburned hydrocarbon radicals from the combustion chamber and the crankcase ventilation gases conducted into the gasifier. These residues shift the air-fuel ratio at idle and in the lower part-load range, so that the mixture becomes leaner, the combustion becomes more incomplete, and thus the proportion of unburned or partially combusted hydrocarbons in the exhaust gas increases. Increasing gasoline consumption is the result.
  • fuel additives are used to clean valves and carburetors or injection systems of gasoline engines (see, for example: M. Rossenbeck in Catalysts, Surfactants, Mineral Oil Additives, Ed. J. Falbe, U Hasserodt, p. 223, G. Thieme Verlag, Stuttgart 1978).
  • Such surface active fuel additives are generally referred to as "detergents”.
  • so-called “dispersants” are often used as surface-active additives, some of which are also suitable for use as detergents in fuel compositions.
  • Such detergents which can originate from a large number of chemical substance classes, such as, for example, polyalkeneamines, polyetheramines, polybutene-Mannich bases or polybutene-succinimides, are generally used in combination with carrier oils and, if appropriate, further additive components, for example corrosion inhibitors and demulsifiers.
  • further additive components for example corrosion inhibitors and demulsifiers.
  • Gasoline fuels with and without such gasoline additive show a different behavior with respect to their lubricating or wear properties in gasoline engines, which is unsatisfactory and should therefore be improved.
  • synergistically effective additive mixtures which can be used as lubricity improvers in fuels and lubricants and the reaction product of a dicarboxylic acid or a dicarboxylic acid derivative with a long-chain, aliphatic amine and a fatty acid ester or a fatty acid ester-containing component, such as.
  • a vegetable oil As a vegetable oil.
  • EP-A-1 246 895 describes other polycyclic aromatic compounds having at least one heteroatom selected from oxygen and nitrogen which is in the heterocyclic or an exocyclic group and which carries at least one C 1 -C 4 -alkyl substituent on the ring. These compounds are particularly suitable as lubricity additives in diesel fuels. According to local teaching may the alkyl substituent may not be bound to the molecule either in the a or in the position to form a ring heteroatom, since otherwise only an insufficient lubricating effect is to be observed. Preferred examples include compounds having at most two heteroatoms, such as in particular 5-methylbenzimidazole, 2-hydroxy-4-methylquinoline, 8-hydroxy-quinaldine and 4-amino-quinaldine.
  • This also has the advantage that compounds of the tolutriazole type, which are already used in fuels as non-ferrous metal corrosion inhibitors (generally in quantities of less than 10 ppm), are supplied to a further use, and thus it is possible to Corrosion protection and lubricating effect with one and the same additive to improve.
  • a first subject of the invention relates to the use of at least one heterocyclic compound of the formula (I)
  • R is H, or C 1 -C 3 alkyl, such as methyl, n- or iso-propyl, as a fretting-reducing additive in fuel compositions.
  • the compound of formula (I) is added to the fuel in a proportion of less than 1000 mg / kg, e.g. in a proportion of 1 to 500 mg / kg or 10 to 250 or 10 to 100 mg / kg, or in a proportion of 1 to ⁇ 50 mg / kg, e.g. 1 to 45 mg / kg.
  • the use of the compound of the formula (I) is preferably carried out as a mixture of compounds which are positional isomers with respect to the ring substituent R.
  • the compound of the formula (I) in particular a mixture of isomers of compounds of the formulas (Ia) and (Ib)
  • the molar ratio of (Ia) (4-alkyl compound) to (Ib) (5-alkyl compound) in a range of 10 to 60 to 90 to 40, such. is about 20 to 40 to 80 to 60 or about 30 to 40 to 70 to 60.
  • the relative proportion of (Ib) is greater than (Ia) and is about 50 to 90, e.g. 55 to 80 mol%, based on the mixture of (Ib) and (Ia).
  • R is methyl.
  • the proportion of (Ib) is about 63 mol% and the proportion of (Ia) about 37 mol%
  • friction modifiers according to the invention in combination with at least one further conventional fuel additive, such as, for example, selected from among detergent additives, carrier oils, corrosion inhibitors and mixtures comprising one or more of these additives
  • a reduction of the fretting wear value (R 1 in ⁇ m), determined as described in the following experimental part, is observed by about 5 to 70, e.g. 5 to 60, 5 to 50, 10 to 60, 10 to 50, 15 to 60 or 15 to 50% compared to the value determined before addition of the additive of the formula (I).
  • the method of determination is based on an HFRR test commonly used in the diesel fuel sector (according to CEC F-06-A-96) but with the measurement taken at room temperature (25 ° C) and under a load of 720g (about 7.06 N).
  • the Krafftscher to be examined are eingiert before distillation to 50 vol .-% by distillation.
  • the invention relates to the use of the above heterocycles in combination with at least one other conventional friction-reducing additive known from the prior art (see, for example, above).
  • a further subject of the invention are fuel compositions comprising, in a main amount of a customary base fuel, an amount of a heterocyclic compound of the formula (I) which reduces the coefficient of friction wear as defined above.
  • the invention also relates to additive concentrates comprising at least one friction-reducing additive as defined above in combination with at least one further customary fuel additive and optionally at least one further conventional friction-reducing additive. Particular preference is given to using the above-described friction modifiers in gasolines.
  • a final object of the invention relates to a process for the preparation of a fuel composition having improved fretting behavior, wherein an effective amount of a heterocyclic compound according to the above definition or an additive concentrate as defined above is added to a commercial fuel composition.
  • the friction modifier formulations according to the invention can be added to the fuels to be additive, individually or in admixture with other effective additive components (coadditives).
  • detergent additives As examples, detergency additives and / or valve seat wear-inhibiting effect (hereinafter referred to as detergent additives) may be cited.
  • This detergent additive has at least one hydrophobic hydrocarbon radical having a number-average molecular weight (Mn) of from 85 to 20,000 and at least one polar group selected from:
  • the hydrophobic hydrocarbon radical in the above detergent additives which provides sufficient solubility in the fuel, has a number average molecular weight (Mn) of from 85 to 20,000, especially from 113 to 10,000, especially from 300 to 5000.
  • Mn number average molecular weight
  • the polypropenyl, polybutenyl and polyisobutenyl radical having in each case Mn 300 to 5000, in particular 500 to 2500, come especially 700 to 2300, into consideration.
  • the preparation route is afforded by chlorination and subsequent deoxidation or by oxidation of the double bond with air or ozone to the carbonyl or carboxyl compound and subsequent amination under reductive (hydrogenating) conditions.
  • amines for example ammonia, monoamines or polyamines, such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine, can be used here.
  • Corresponding additives based on polypropene are described in particular in WO-A-94/24231.
  • monoamino groups (a) -containing additives are the compounds obtainable from polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols, as described in particular in DE-A-196 20 262.
  • These reaction products typically are mixtures of pure nitropolyisobutenes (e.g., alpha, beta-dinitropolyisobutene) and mixed hydroxynitropolyisobutenes (e.g., alpha-nitro-beta-hydroxy polyisobutene).
  • Carboxyl groups or their alkali metal or alkaline earth metal salts (d) containing additives are preferably copolymers of C 2 -C 40 olefins with maleic anhydride having a total molecular weight of 500 to 20 000, the carboxyl groups wholly or partially to the alkali metal or alkaline earth metal salts and a remaining Rest of the carboxyl groups are reacted with alcohols or amines.
  • Such additives are known in particular from EP-A-307 815.
  • Such additives are mainly used to prevent valve seat wear and, as described in WO-A-87/01126, can be advantageously used in combination with conventional fuel detergents such as poly (iso) butenamines or polyetheramines.
  • Sulphonic acid groups or their alkali metal or alkaline earth metal salts (e) containing additives are preferably alkali metal or alkaline earth metal salts of a sulfosuccinic acid alkyl ester, as described in particular in EP-A-639 632.
  • Such additives are mainly used to prevent valve seat wear and can be used to advantage in combination with conventional fuel detergents such as poly (iso) butenamines or polyetheramines.
  • Polyoxy-C 2 -C 4 alkylene groupings (f) containing additives are preferably polyether or polyetheramines, which by reaction of C 2 -C 6 o-alkanols, C6-C30 alkanediols, mono- or di-C 2 -C 3 o-alkylamines, Ci-Cao-Alkylcyclohexanolen or C 1 - C 30 alkylphenols with 1 to 30 moles of ethylene oxide and / or propylene oxide and / or Buty- lenoxid per hydroxyl group or amino group and, in the case of polyetheramines, by subsequent reductive amination with Ammonia, monoamines or polyamines are available.
  • Such products are described in particular in EP-A-310 875, EP-A-356 725, EP-A-700 985 and US-A-4 877 416.
  • polyethers such products also meet carrier oil properties. Typical examples of these are tridecanol or Isotridecanolbutoxylate, Isononylphenolbutoxylate and Polyisobute- nolbutoxylate and propoxylates and the corresponding reaction products with ammonia.
  • Carboxylic ester groups (g) containing additives are preferably esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, especially those having a minimum viscosity of 2 mm 2 / s at 100 0 C, as described in particular in DE-A-38 38 918 are described.
  • Aliphatic or aromatic acids can be used as the mono-, di- or tricarboxylic acids, and the ester alcohols or polyols used are, above all, long-chain representatives with, for example, 6 to 24 carbon atoms.
  • esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, iso-nonanol, iso-decanol and isotridecanol. Such products also fulfill carrier oil properties.
  • derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
  • Such gasoline additives are described in particular in US Pat. No. 4,849,572.
  • Mannich reaction of substituted phenols with aldehydes and mono- or polyamines generated groupings (i) containing additives are preferably reaction products of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or dimethylaminopropylamine.
  • Such "polyisobutene-Mannich bases" are described in particular in EP-A-831 141.
  • additive formulations according to the invention can moreover be combined with even further customary components and additives.
  • Here are primarily carrier oils without pronounced detergent action to call.
  • Suitable mineral carrier oils are fractions obtained in petroleum processing, such as bright stock or base oils with viscosities such as, for example, from the class SN 500-2000; but also aromatic hydrocarbons, paraffinic hydrocarbons and alkoxyalkanols.
  • An accumulating as "hydrocrack oil” bekann ⁇ te and in the refining of mineral oil fraction is also useful (vacuum distillate cut obtainable with a boiling range of about 360-500 0 C 1 from catalytic high pressure table hydrogenated and isomerized and also deparaffinized natural mineral oil).
  • mineral carrier oils are mixtures of the abovementioned mineral carrier oils.
  • Examples of synthetic carrier oils which can be used according to the invention are selected from: polyolefins (polyalphaolefins or polyethylenemolefins), (poly) esters, (poly) ly) alkoxylates, polyethers, aliphatic polyetheramines, alkylphenol-initiated polyethers, alkylphenol-initiated polyetheramines and carboxylic acid esters of long-chain alkanols.
  • suitable polyethers or polyetheramines are preferably compounds containing polyoxy-C 2 -C 4 -alkylene groups which are prepared by reacting C 2 -C 60 -alkanols, C 6 -C 30 -alkanediols, mono- or di-C 2 -C 3 o-alkylamines, C 1 -C 30 -
  • Such products are described in particular in EPA-310 875, EP-A-356 725, EP-A-700 985 and US-A-4,877,416.
  • the polyetheramines used can be poly-C 2 -C 6 -alkylene oxide amines or functional derivatives thereof. Typical examples of these are tridecanol or Isotridecanolbutoxylate, Isononylphenolbutoxylate and Polyisobutenolbutoxylate and propoxylates and the corresponding reaction products with ammonia.
  • carboxylic acid esters of long-chain alkanols are in particular esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, as described in particular in DE-A-38 38 918.
  • mono-, di- or tricarboxylic acids it is possible to use aliphatic or aromatic acids, especially suitable ester alcohols or polyols are long-chain representatives having, for example, 6 to 24 carbon atoms.
  • esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, isononanol, isodecanol and isotricanecanol, such as e.g. Di (n- or iso-tridecyl) phthalate.
  • suitable synthetic carrier oils are alcohol-started polyethers with about 5 to 35, such as about 5 to 30, C 3 -C 6 alkylene oxide units, such as selected from propylene oxide, n-butylene oxide and i-butylene oxide units, or mixtures thereof.
  • suitable starter alcohols are long-chain alkanols or substituted long-chain alkyl phenols, wherein the long chain alkyl group is 8 -alkyl radical, in particular a straight-chain or branched C 6 -C.
  • Preferred examples are tridecanol and nonylphenol.
  • suitable synthetic carrier oils are alkoxylated alkylphenols, as described in DE-A-10 102 913.6
  • corrosion inhibitors for example based on film-forming ammonium salts of organic carboxylic acids or of heterocyclic aromatics in the case of non-ferrous metal corrosion protection
  • Antioxidants or stabilizers for example based on amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof or of phenols such as 2,4-di-te ⁇ t-butylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpropionklare
  • demulsifiers demulsifiers
  • Antistatic agents Metallocene such as ferrocene; methylcyclopentadienyl
  • Lubricity improvers other than the triazoles according to the invention, such as certain fatty acids, alkenylsuccinic esters, bis (hydroxyalkyl) fatty amines, hydroxyacetamides or ricin oil; as well as dyes (markers).
  • amines are added to lower the pH of the fuel.
  • the components or additives can be added to the fuel individually or as a previously prepared concentrate (additive package) together with the friction modifier according to the invention.
  • the said detergent additives with the polar groups (a) to (i) are added to the fuel usually in an amount of 10 to 5000 ppm by weight, in particular 50 to 1000 ppm by weight.
  • the other components and additives mentioned are, if desired, added in conventional amounts.
  • a gasoline having an aromatic content of at most 60 e.g. a maximum of 42 or a maximum of 35% by volume and / or a sulfur content of not more than 2000, e.g. maximum 150 or maximum 10 ppm by weight possible.
  • the aromatics content of the gasoline is, for example, from 0 to 50, e.g. 30 to 42 vol.%, In particular 32 to 40 vol.%, Or at most 35 vol.%.
  • Sulfur content of the gasoline is, for example, 2 to 500, e.g. 5 to 100 ppm by weight, or maximally 0 ppm by weight.
  • the gasoline may, for example, have an olefin content of up to 50% by volume, e.g. from 6 to 21% by volume, especially 7 to 18% by volume; a benzene content of up to 5% by volume, e.g. 0.5 to 1.0% by volume, in particular 0.6 to 0.9% by volume and / or an oxygen content of up to 25% by volume, such as e.g. up to 10 wt .-% or 1, 0 to 2.7 wt .-%, in particular from 1, 2 to 2.0 wt .-%, have.
  • an olefin content of up to 50% by volume, e.g. from 6 to 21% by volume, especially 7 to 18% by volume
  • a benzene content of up to 5% by volume e.g. 0.5 to 1.0% by volume, in particular 0.6 to 0.9% by volume
  • an oxygen content of up to 25% by volume such as e.g. up to 10 wt .-% or 1, 0 to 2.7 w
  • gasoline fuels may be mentioned by way of example, which at the same time have an aromatic content of not more than 38 or 35% by volume, an olefin content of not more than 21% by volume, a sulfur content of not more than 50 or 10 ppm by weight, a benzene content of not more than 1, 0 vol .-% and an oxygen content of 1, 0 to 2.7% by weight.
  • the content of alcohols and ethers in gasoline can vary over a wide range. Examples of typical maximum contents are 15% by volume for methanol, 65% by volume for ethanol, 20% by volume for isopropanol, 15% by volume for tert-butanol, 20% by volume for isobutanol and 20% by weight for isobutanol for ethers with 5 or more C atoms in the molecule 30 vol .-%.
  • the summer vapor pressure of the gasoline is usually not more than 70 kPa, in particular 60 kPa (each at 37 ° C).
  • the ROZ of the gasoline is usually 75 to 105.
  • a common range for the corresponding MOZ is 65 to 95.
  • the specified specifications are determined by conventional methods (DIN EN 228).
  • HFRR High Frequency Reciprocating Rig
  • the used petrol (OK) (typical petrol according to EN 228) was concentrated by distillation to 50 Vol .-% before the measurements.
  • For this ver ⁇ uses an MP 628 distillation unit of the company. Herzog, Lauda-Königshofen, Germany. This 50% residue was used in the examination in Verschl boss ⁇ measuring device to determine the blank value.
  • To this residue according to the examples given below in Table 1, the further additives were added and the fretting values were determined according to the method given above.
  • the re- resulting frictional wear values (R) are given in micrometers ( ⁇ m); the lower the value, the lower the wear that occurs.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne l'utilisation d'au moins un composé hétérocyclique de formule (I), dans laquelle R représente un atome d'hydrogène ou un groupe alkyle C<sub
EP05783500A 2004-08-05 2005-08-04 Composes heterocycliques contenant de l'azote utilises comme additif dans des carburants pour reduire l'usure de contact Withdrawn EP1786888A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004038113A DE102004038113A1 (de) 2004-08-05 2004-08-05 Stickstoffhaltige heterocyclische Verbindungen als Reibverschleißvermindernder Zusatz zu Kraftstoffen
PCT/EP2005/008468 WO2006015800A1 (fr) 2004-08-05 2005-08-04 Composes heterocycliques contenant de l'azote utilises comme additif dans des carburants pour reduire l'usure de contact

Publications (1)

Publication Number Publication Date
EP1786888A1 true EP1786888A1 (fr) 2007-05-23

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EP05783500A Withdrawn EP1786888A1 (fr) 2004-08-05 2005-08-04 Composes heterocycliques contenant de l'azote utilises comme additif dans des carburants pour reduire l'usure de contact

Country Status (15)

Country Link
US (2) US7850744B2 (fr)
EP (1) EP1786888A1 (fr)
JP (1) JP4940138B2 (fr)
KR (1) KR101218902B1 (fr)
CN (1) CN1993450B (fr)
AR (2) AR051366A1 (fr)
AU (1) AU2005270349A1 (fr)
BR (1) BRPI0514137B1 (fr)
CA (1) CA2575494C (fr)
DE (1) DE102004038113A1 (fr)
MX (1) MX2007000840A (fr)
MY (1) MY145663A (fr)
SG (2) SG155185A1 (fr)
WO (1) WO2006015800A1 (fr)
ZA (1) ZA200701847B (fr)

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CN1993450B (zh) 2011-11-16
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CN1993450A (zh) 2007-07-04
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AR082343A2 (es) 2012-11-28
BRPI0514137B1 (pt) 2014-09-16
WO2006015800A1 (fr) 2006-02-16
BRPI0514137A (pt) 2008-05-27
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CA2575494C (fr) 2013-07-02
AU2005270349A1 (en) 2006-02-16
US8814957B2 (en) 2014-08-26
US20080190014A1 (en) 2008-08-14
JP4940138B2 (ja) 2012-05-30
US7850744B2 (en) 2010-12-14
KR101218902B1 (ko) 2013-01-07
DE102004038113A1 (de) 2006-03-16
SG155185A1 (en) 2009-09-30
AR051366A1 (es) 2007-01-10
SG10201404612PA (en) 2014-09-26
KR20070051293A (ko) 2007-05-17

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