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
  • C10L1/234—Macromolecular compounds
  • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
• • 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
  • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
  • C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
• • 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
  • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular 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
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
• • 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
• • 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
  • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
• • 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
  • C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
• • 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
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
• • 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
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters

Definitions

• This invention relates to gasoline compositions.
• WO 9421753 discloses fuels for internal combustion engines, including both gasoline and diesel fuel, containing proportions (e.g. 1 to 90% v, 1 to 50% v, preferably 1 to 20% v) of esters of C 4 to C 6 keto-carbonic acids, preferably levulinic acid, with C 1 to C 22 alcohols.
• Esters with C 1 to C 8 alcohols are described as being particularly suitable for inclusion in gasolines, and esters with C 9 to C 22 alcohols are described as being particularly suitable for inclusion in diesel fuels.
• Examples in WO 9421753 are all of the inclusion of quantities of levulinate esters in gasolines, for improvement in octane numbers (RON and MON).
• 10% v methyl levulinate is incorporated in different base gasolines.
• Examples 2 to 6 employ, respectively, ethyl levulinate, n-propyl levulinate, isopropyl levulinate, isobutyl levulinate and sec-butyl levulinate.
• Examples 8 and 9 employ 10% v of mixtures of methyl levulinate and methyl formate, in 1:1 and 2:1 ratios, respectively.
• Example 11 employs a range of proportions from 5% v to 90% v of methyl levulinate in unleaded Eurosuper gasoline.
• WO 03002696 discloses a fuel composition incorporating levulinic acid, or a functional derivative thereof, with the object of providing more oxygen by volume than ethanol or traditional oxygenates such as MTBE or ETBE, giving little or no increase in fuel Reid vapour pressure and little or no effect on the flash point of the base fuel.
• the functional derivative is preferably an alkyl derivative, preferably a C 1 to C 10 alkyl derivative. Ethyl levulinate is said to be preferred, with methyl levulinate a preferred alternative.
• the levulinic acid or functional derivative is preferably used to form 0.1 to 5% v of the fuel.
• WO 03002696 further incorporates 0.1 to 5% v of a further additive selected from the groups consisting of:
• the fuel is substantially free of alkoxylated compounds and of long chain alkyl alcohols, but it contains an additive of formula R—CO—NR 1 R 2 , where R is a saturated or unsaturated, linear or branched, alkyl radical having 6 to 21 carbon atoms (corresponding to number average molecular weight in the range 85 to 295), and R 1 and R 2 each independently represent a C 1 to C 4 hydroxyalkyl radical.
• An alternative additive (Page 8, lines 9, 10) comprises an oleic alkanolamide and an alkoxylated oleic acid.
• a fuel composition which incorporates the levulinic acid, or functional derivative thereof, together with a nitrogen source in the form of (Page 9 lines 8 to 15) a nitrogen compound selected from the group consisting of ammonia, hydrazine, alkyl hydrazine, dialkyl hydrazine, urea, ethanolamine, monoalkyl ethanolamine, and dialkyl ethanolamine wherein alkyl is independently selected from methyl, ethyl, n-propyl or isopropyl. Urea is preferred.
• the nitrogen compound may be an anhydrous compound or a hydrous compound, e.g. an aqueous solution, and may be up to a 5% w/w aqueous solution.
• Cetane boosters, demulsifers and bio-diesel type fuels may also be present (Page 10, lines 1 to 29).
• a gasoline composition comprising a major amount of a gasoline suitable for use in a spark ignition engine, 1 to 15% v of ethyl levulinate, and 20 to 2000 ppmw of a nitrogen-containing detergent containing a hydrocarbyl group having a number average molecular weight in the range 750 to 6000.
• the preparation of such a composition, and its use in operation of a spark-ignition engine is also provided.
• gasoline compositions containing ethyl levulinate together with particular nitrogen-containing detergents can give enhanced engine cleanliness performance, and that gasoline compositions containing ethyl levulinate are more compatible with certain elastomeric seal materials than gasoline compositions containing similar concentrations of methyl levulinate.
• Levulinate esters esters of levulinic acid
• furfuryl acetate is described in Zh. Prikl. Khim. (Leningrad) (1969) 42(4), 958-9, and in particular the methyl, ethyl, propyl, butyl, pentyl and hexyl esters.
• the ethyl levulinate concentration in the gasoline composition accords with one or more of the following parameters:
• the gasoline composition preferably contains 50 to 1500 ppmw of the nitrogen-containing detergent, and more preferably 50 to 500 ppmw thereof. Quantities in the range 80 to 250 ppmw, e.g. 100 to 150 ppmw, are very suitable.
• the nitrogen-containing detergent containing a hydrocarbyl group having a number average molecular weight (Mn) in the range 750 to 6000 may be an amine, e.g. a polyisobutylene mono-amine or polyamine, such as a polyisobutylene ethylene diamine, or N-polyisobutenyl-N′,N′-dimethyl-1,3-diaminopropane, or amide e.g. a polyisobutenyl succinimide, and are variously described, for example, in WO 0132812 and U.S. Pat. No. 5,855,629 which disclosure is hereby incorporated by reference.
• the nitrogen-containing detergent may be a Mannich amine detergent, for example a Mannich amine detergent as described in U.S. Pat. No. 5,725,612, which disclosure is hereby incorporated by reference.
• a particularly preferred nitrogen-containing detergent is hydrocarbyl amine of formula R 1 -NH 2 , wherein R 1 represents a group R 2 or a group R 2 -CH 2 — and R 2 represents a hydrocarbyl group having a number average molecular weight in the range 750 to 6000, preferably in the range 900 to 3000, more preferably 950 to 2000, and most preferably in the range 950 to 1350, e.g. a polybutenyl or polyisobutenyl group having a number average molecular weight in the range 950 to 1050.
• the nitrogen-containing detergents are known materials and may be prepared by known methods or by methods analogous to known methods.
• U.S. Pat. No. 4,832,702 which disclosure is hereby incorporated by reference, describes the preparation of polybutenyl and polyisobutenyl amines from an appropriate polybutene or polyisobutene by hydroformylation and subsequent amination of the resulting oxo product under hydrogenating conditions.
• Suitable hydrocarbyl amines are obtainable from BASF A.G., under the trade mark “Kerocom”.
• the gasoline composition may additionally contain one or more carrier fluids, corrosion inhibitors, anti-oxidants, dyes, dehazers, metal deactivators, detergents other than a nitrogen-containing detergent containing a hydrocarbyl group as defined above (e.g. a polyether amine), friction modifiers, diluents and markers.
• carrier fluids corrosion inhibitors, anti-oxidants, dyes, dehazers, metal deactivators, detergents other than a nitrogen-containing detergent containing a hydrocarbyl group as defined above (e.g. a polyether amine), friction modifiers, diluents and markers.
• carrier fluids are polyolefins, e.g. polyisobutylene and polyalphaolefins, and polyoxyalkylene compounds.
• Carrier fluids may conveniently be employed in total concentrations in the range 20 to 8000 ppmw, e.g. 50 to 500 ppmw.
• Polyalphaolefin carrier fluids are primarily trimers, tetramers and pentamers, and synthesis of such materials is outlined in Campen et al. “Growing use of synlubes”, Hydrocarbon Processing, February 1982, Pages 75 to 82.
• the polyalphaolefin may be unhydrotreated, but it is preferably a hydrogenated oligomer.
• the polyalphaolefin is preferably derived from an alphaolefinic monomer containing from 8 to 12 carbon atoms. Furthermore, it preferably has viscosity at 100° C. in the range 6 ⁇ 10 ⁇ 6 to 1 ⁇ 10 ⁇ 5 m 2 /s (6 to 10 centistokes). Polyalphaolefins derived from decene-1 are very suitable. Polyalphaolefin having a viscosity at 100° C. of 8 ⁇ 10 ⁇ 6 m 2 /s (8 centistokes) are very suitable.
• Polyoxyalkylene carrier fluids which are very effective, preferably have the formula II wherein R 3 and R 4 independently represent hydrogen atoms or hydrocarbyl, preferably C 1-40 hydrocarbyl, e.g. alkyl, cycloalkyl, phenyl or alkyl-phenyl groups, each R 5 independently represents an alkylene, preferably C 2-8 alkylene, group, and p is such that Mn of the polyoxyalkylene compound is in the range 400 to 3000, preferably 700 to 2000, more preferably 1000 to 2000.
• R 3 represents a C 8-20 alkyl group and R 4 represents a hydrogen atom.
• R 3 preferably represents a C 8-18 alkyl group, more preferably a C 8-15 alkyl group.
• R 3 may conveniently be a mixture of C 8-15 alkyl groups.
• each group R 5 are preferably 1,2 alkylene groups.
• each group R 5 independently represents a C 2-4 alkylene group, e.g. an ethylene, 1,2-propylene or 1,2-butylene group. Very effective results have been obtained when each group R 5 represents a 1,2-propylene group.
• Number average molecular weights e.g. of hydrocarbons such as polyalkenes, may be determined by several techniques which give closely similar results. Conveniently Mn may be determined by vapour phase osmometry (VPO) (ASTM D 3592) or by modern gel permeation chromatography (GPC), e.g. as described for example in W. W. Yau, J. J. Kirkland and D. D. Bly, “Modern Size Exclusion Liquid Chromatography”, John Wiley and Sons, New York, 1979. Where the formula of a compound is known, the number average molecular weight can be calculated as its formula weight.
• VPO vapour phase osmometry
• GPC gel permeation chromatography
• Very suitable friction modifiers are the fatty acid salt friction modifiers disclosed in DE-A-19955651 (BASF) (e.g. that described in Example 1 thereof), e.g. in an amount in the range 5 to 1000 ppmw, preferably 25 to 400 ppmw, and more preferably 50 to 200 ppmw.
• gasolines suitable for use in spark ignition engines are mixtures of hydrocarbons having boiling points in the range from 25° C. to 232° C. and comprising mixtures of saturated hydrocarbons, olefinic hydrocarbons and aromatic hydrocarbons.
• Preferred are gasoline blends having a saturated hydrocarbon content ranging from 40 to 80 per cent volume, an olefinic hydrocarbon content ranging from 0 to 30 per cent volume and an aromatic hydrocarbon content ranging from 10 to 60 per cent volume.
• the gasoline can be derived from straight run gasoline, polymer gasoline, natural gasoline, dimer- or trimerised olefins, synthetically produced aromatic hydrocarbon mixtures from thermally or catalytically reformed hydrocarbons, or from catalytically cracked or thermally cracked petroleum stocks, or mixtures thereof.
• the hydrocarbon composition and octane level of the gasoline are not critical.
• the octane level, (R+M)/2, will generally be above 85.
• Any conventional gasoline can be used.
• hydrocarbons can be replaced by up to substantial amounts of conventional alcohols or ethers conventionally known for use in gasoline.
• the gasoline is preferably lead-free, and this may be required by law. Where permitted, lead-free anti-knock compounds and/or valve-seat recession protectant compounds (e.g. known potassium salts, sodium salts or phosphorous compounds) may be present.
• lead-free anti-knock compounds and/or valve-seat recession protectant compounds e.g. known potassium salts, sodium salts or phosphorous compounds
• Modern gasolines are inherently low-sulphur fuels, e.g. containing less than 200 ppmw sulphur.
• amounts (concentrations) (% v) (ppmw) of components are of active matter, i.e. exclusive of volatile solvents/diluent materials.
• the invention further provides a process for the preparation of a gasoline composition of the invention as defined above which comprises bringing into admixture the gasoline, the ethyl levulinate and the nitrogen-containing detergent.
• the fatty acid salt, the co-additive, and any additional components such as corrosion inhibitors, anti-oxidants, etc., as listed above may be co-mixed, preferably together with suitable diluent(s), in an additive concentrate, and the additive concentrate may be dispersed into gasoline, in suitable quantity to result in a composition of the invention.
• the invention also provides a method of operating a spark-ignition engine, which comprises bringing into the combustion chambers of said engine a gasoline composition of the invention as defined above.
• the method of the invention may lead to any of a number of advantageous effects, including good engine keep-clean performance, especially in relation to inlet-system deposits, and clean-up performance can be achieved at the higher concentrations of the nitrogen-containing detergent, advantageous octane performance (RON and MON) and advantageous Reid vapour pressure.
• base fuel used was an unleaded gasoline (95 ULG) of RON 98.9, MON 86.6, and having sulphur content (ASTM D 2622-94) of 138 ppmw, aromatics content of 50.7% v/v and olefins content 7.5% v/v (ASTM D6623-01 (procedure C)), Density (DIN 51757/V4) 779.1 kg/m 3 , distillation (ISO 3405/88) IBP 35.42, 95% v/v 174.4, FBP 203° C.
• Test fuels were subjected to engine testing according to the following procedure.
• the engine was run for a period of 69 hours under a test procedure corresponding to that of CEC-F-05-A-93, except that the Toyota 3S-FE engine was used in place of the Mercedes Benz M 102 E engine specified in the CEC-F-05-A-93 procedure, and the torque values differ from those specified in CEC-F-05-A-93 to compensate for the different BMEP (break mean effective pressure) values achieved by the Mercedes Benz M 102 E and the Toyota 3S-FE engines.
• BMEP break mean effective pressure
• IVD inlet valve deposit
• gasoline compositions were prepared containing 5% by volume of ethyl levulinate and 380 ppmw of DP (Example 1), 380 ppmw of DP (Comparative Example A), 5% by volume of ethyl levulinate (Comparative Example B), and these were tested by the above procedure in comparison with base fuel (Comparative Example C). Results are given in Table 1.
• Ethyl levulinate DP IVD Example (% v) (ppmw) (mg/valve) 1 5 380* 4 Comparative A 0 380* 26 Comparative B 5 0 111 Comparative C 0 0 142 *corresponds to about 105 ppmw of PIBA active matter
• gasoline compositions using a base fuel prepared to the same recipe as that of Example 1, were prepared containing 5% by volume of ethyl levulinate and 225 ppmw PIBA (Example 2) and 225 ppmw PIBA, (Comparative Example D) and these were tested by the above procedure. Results are given in Table 2.
• Example 2 Ethyl levulinate DP IVD Example (% v) (ppmw) (mg/valve) 2 5 225* 13 Comparative D 0 225* 24 *corresponds to 110 to 125 ppmw of PIBA active matter
• the test procedure was a modified version of ISO 1817:1998.
• Two elastomeric materials were tested, viz. a hydrogenated nitrile elastomer (“Elast-o-Lion” 280 (trade mark), ex James Walker & Co. Ltd., UK) and a fluorocarbon tetrapolymer elastomer (“Viton” (trade mark) LR 6316, ex James Walker & Co. Ltd., UK).
• Volume and Shore hardness values of elastomer samples of dimensions 50 mm ⁇ 25 mm ⁇ 3 mm were measured before testing, and again after immersion in 100 ml of test fluid at ambient temperature (20° C.) for 168 hours. Samples were weighed in air and in water (for assessment of volume).

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

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• 2004
  • 2004-07-08 WO PCT/EP2004/051423 patent/WO2005014759A1/en active Search and Examination
  • 2004-07-08 CN CNB200480020221XA patent/CN100432196C/zh not_active Expired - Fee Related
  • 2004-07-08 CA CA2533001A patent/CA2533001C/en not_active Expired - Fee Related
  • 2004-07-08 EP EP04741982A patent/EP1651740B1/en not_active Not-in-force
  • 2004-07-08 BR BRPI0412640-8A patent/BRPI0412640A/pt not_active IP Right Cessation
  • 2004-07-08 AT AT04741982T patent/ATE556128T1/de active
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  • 2004-07-08 NZ NZ544457A patent/NZ544457A/en unknown
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  • 2004-07-13 US US10/889,790 patent/US20050016058A1/en not_active Abandoned
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