EP1541663A1 - Huiles combustibles comprenant des distillats moyens et des huiles d'origine végétale ou animale et ayant des propriétés à froid améliorées. - Google Patents

Huiles combustibles comprenant des distillats moyens et des huiles d'origine végétale ou animale et ayant des propriétés à froid améliorées. Download PDF

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Publication number
EP1541663A1
EP1541663A1 EP20040028307 EP04028307A EP1541663A1 EP 1541663 A1 EP1541663 A1 EP 1541663A1 EP 20040028307 EP20040028307 EP 20040028307 EP 04028307 A EP04028307 A EP 04028307A EP 1541663 A1 EP1541663 A1 EP 1541663A1
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Prior art keywords
alkyl
fuel oil
oil composition
composition according
acid
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German (de)
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EP1541663B1 (fr
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Matthias Dr. Krull
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Clariant Produkte Deutschland GmbH
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Clariant GmbH
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    • 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
    • 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
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/1955—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by an alcohol, ether, aldehyde, ketonic, ketal, acetal radical
    • 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
    • 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
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
    • 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
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
    • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
    • 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
    • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
    • 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
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-carboxylic
    • 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
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides

Definitions

  • the present invention relates to mineral fuel oils containing ingredients of vegetable or animal origin with improved cold properties and the Use of an additive as a cold flow improver for such fuel oils.
  • biofuels include, in particular, natural oils and fats of plant or animal origin. These are typically triglycerides of fatty acids with 10 to 24 C atoms, which have a calorific value comparable to conventional fuels, but at the same time are considered less harmful to the environment.
  • Biofuels ie fuels derived from animal or plant material, are obtained from renewable sources and thus produce only as much CO 2 as was previously converted into biomass. It has been reported that combustion produces less carbon dioxide than equivalent amounts of petroleum distillate fuel, eg, diesel fuel, and that very little sulfur dioxide is produced. In addition, they are biodegradable.
  • Oils obtained from animal or vegetable material are mainly metabolites comprising triglycerides of monocarboxylic acids, eg of acids having 10 to 25 carbon atoms, and the formula in which R is an aliphatic radical of 10 to 25 carbon atoms, which may be saturated or unsaturated.
  • oils contain glycerides of a number of acids whose Number and variety varies with the source of the oil, and they may additionally Contain phosphoglycerides.
  • Such oils may be known in the art Procedures are obtained.
  • EP-B-0 665 873 discloses a fuel oil composition containing a biofuel, a petroleum based fuel oil and an additive comprising (a) an oil soluble Ethylene copolymer or (b) a comb polymer or (c) a polar nitrogen compound or (d) a compound in which at least one substantially linear alkyl group having 10 to 30 carbon atoms with a non-polymeric organic radical is connected to provide at least one linear chain of atoms that the Carbon atoms of the alkyl groups and one or more non-terminal ones Including oxygen atoms, or (e) one or more of components (a), (b), (c) and (d).
  • EP-B-0 153 176 discloses the use of polymers based on unsaturated C 4 -C 8 dicarboxylic acid di-alkyl esters having average alkyl chain lengths of 12 to 14 as cold flow improvers for certain petroleum distillate fuel oils.
  • Suitable comonomers are unsaturated esters, in particular vinyl acetate, but also ⁇ -olefins.
  • EP-B-0 746 598 discloses comb polymers as a cold additive in fuel oils containing a Cloud point of at most -10 ° C.
  • Another object of the invention is the use of the above defined Additive containing the components A) and B), for improving the Cold flow properties of fuel oil compositions F) containing Fuel oils mineral (F1) and animal and / or vegetable (F2) origin.
  • Another object of the invention is a process for the preparation of Fuel oil compositions F) containing fuel oils mineral (F1) and animal and / or vegetable (F2) origin, with improved cold properties, by mixing the mixture of fuel oils mineral (F1) and animal and / or vegetable (F2) origin of the above-defined additive containing the Ingredients A) and B), added.
  • Preferred oils of mineral origin are middle distillates.
  • Particularly preferred are mixtures which are 2 to 50% by volume, in particular 5 to 40% by volume and especially 10 to 30% by volume of biofuel oils contain. These mixtures give the additives of the invention superior Cold properties.
  • R assumes values between 11.5 and 13.5, in particular 12.0 to 13.0.
  • Suitable ethylene copolymers A) are those which contain from 8 to 21 mol% of one or more vinyl and / or (meth) acrylic esters and from 79 to 92% by weight of ethylene. Particularly preferred are ethylene copolymers with 10 to 18 mol% and especially 12 to 16 mol% of at least one vinyl ester.
  • Suitable vinyl esters are derived from fatty acids with linear or branched alkyl groups having 1 to 30 carbon atoms.
  • Examples which may be mentioned are vinyl acetate, vinyl propionate, vinyl butyrate, vinyl hexanoate, Vinylheptanoat, vinyl octanoate, vinyl laurate and vinyl stearate and branched fatty acid based esters of vinyl alcohol such as vinyl isobutyrate, vinyl pivalate, vinyl 2-ethylhexanoate, iso-Nonanklarevinylester, Neononanklavinylester, vinyl neodecanoate and Neoundecanklavinylester.
  • esters of acrylic and methacrylic acid having 1 to 20 C atoms in the alkyl radical such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n- and isobutyl (meth) acrylate, Hexyl, octyl, 2-ethylhexyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl (meth) acrylate and mixtures of two, three, four or more of these comonomers.
  • Particularly preferred terpolymers of 2-Ethylhexanklarvinylesters, the Neononanoic or vinyl neodecanoate contain except Ethylene preferably 3.5 to 20 mol%, in particular 8 to 15 mol% of vinyl acetate and 0.1 to 12 mol%, in particular 0.2 to 5 mol% of the respective long-chain vinyl ester, the total comonomer content being between 8 and 21 mol%, preferably between 12 and 18 mol% is.
  • copolymers contain besides ethylene and 8 to 18 mol% of vinyl esters or 0.5 to 10 mol% of olefins such as propene, butene, isobutylene, Hexene, 4-methylpentene, octene, diisobutylene and / or norbornene.
  • olefins such as propene, butene, isobutylene, Hexene, 4-methylpentene, octene, diisobutylene and / or norbornene.
  • the copolymers A preferably have molecular weights which correspond to melt viscosities at 140 ° C. of from 20 to 10,000 mPas, in particular from 30 to 5,000 mPas and especially from 50 to 1,000 mPas.
  • the determined by 1 H NMR spectroscopy degrees of branching are preferably between 1 and 9 CH 3/100 CH 2 groups, especially between 2 and 6 CH 3/100 CH 2 groups, such as 2.5 to 5 CH 3/100 CH 2 groups not derived from the comonomers.
  • the copolymers (A) are prepared by the usual copolymerization methods such as for example suspension polymerization, solvent polymerization, Gas phase polymerization or high-pressure mass polymerization produced.
  • the Polymerization in a multizone reactor the difference in temperature between the peroxide dosages along the tubular reactor is kept as low as possible, i. ⁇ 50 ° C, preferably ⁇ 30 ° C, in particular ⁇ 15 ° C.
  • the differ Temperature maxima in the individual reaction zones by less than 30 ° C, more preferably less than 20 ° C and especially less than 10 ° C.
  • the reaction of the monomers is by free-radical initiators (Radical chain starter) initiated.
  • This class of substance includes e.g. Oxygen, Hydroperoxides, peroxides and azo compounds such as cumene hydroperoxide, t-butyl hydroperoxide, dilauroyl peroxide, dibenzoyl peroxide, bis (2-ethylhexyl) peroxide carbonate, t-butyl perpivalate, t-butyl per-maleate, t-butyl perbenzoate, dicumyl peroxide, t-butyl cumyl peroxide, di- (t-butyl) peroxide, 2,2'-azobis (2-methylpropanonitrile), 2,2'-azobis (2-methylbutyronitrile).
  • the initiators are used singly or as a mixture of two or more substances in amounts of 0.01 to 20 wt .-%, preferably 0.05 to 10 wt .
  • High pressure bulk polymerization is used in known high pressure reactors, e.g. Autoclaves or tube reactors, discontinuous or continuous, Tube reactors have proven particularly useful. Solvents such as aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures, benzene or toluene, may be included in the reaction mixture. Preferably, this is essentially solvent-free operation.
  • Polymerization is the mixture of the monomers, the initiator and, if used, the moderator, a tubular reactor via the reactor inlet and above supplied to one or more side branches.
  • Preferred moderators are for example Hydrogen, saturated and unsaturated hydrocarbons such as propane or propene, aldehydes such as, for example, propionaldehyde, n-butyraldehyde or isobutyraldehyde, Ketones such as acetone, methyl ethyl ketone, Methyl isobutyl ketone, cyclohexanone and alcohols such as butanol.
  • the Comonomers as well as moderators can do this together with ethylene as well as metered separately via side streams in the reactor.
  • the Monomer streams may be composed differently (EP-A-0 271 738 and EP-A-0 922 716).
  • the mixtures differ based on the mixtures lying polymers in at least one characteristic.
  • they can contain different comonomers, different comonomer contents, Have molecular weights and / or degrees of branching.
  • the mixing ratio the various ethylene copolymers is preferably between 20: 1 and 1:20, preferably 10: 1 to 1:10, in particular 5: 1 to 1: 5.
  • the copolymers B are derived from alkyl acrylates, alkyl methacrylates, alkyl acrylamides, Alkylmethacrylamiden, alkyl vinyl esters, alkyl vinyl ethers, Alkylallylethern and Alkyldiketenen having 8 to 16 carbon atoms in the alkyl radical. These comonomers are in the hereinafter referred to as comonomers B1).
  • the copolymers which are Constituent B to those containing comonomers derived from esters, Amides and / or imides of ethylenically unsaturated monocarboxylic acids having 3 to 8 Carbon atoms are derived with alcohols or amines, wherein the alcohols or Amine carry alkyl radicals having 8 to 16 carbon atoms.
  • the copolymers B) may also contain comonomers B2) which comprise i) esters, amides and / or imides of ethylenically unsaturated dicarboxylic acids having 4 to 8 C atoms and alcohols or amines having 8 to 16 C atoms in the alkyl radicals and / or or ii) C 10 to C 20 olefins.
  • comonomers B2 comprise i) esters, amides and / or imides of ethylenically unsaturated dicarboxylic acids having 4 to 8 C atoms and alcohols or amines having 8 to 16 C atoms in the alkyl radicals and / or or ii) C 10 to C 20 olefins.
  • the alkyl radicals of the comonomers B1 and B2 are preferably linear, but may also be minor amounts of branched isomers of up to 30 mol%, preferably up to to 20 mol% and especially 2 to 5 mol%.
  • the proportion of comonomers B1) and optionally B2) in the polymer is preferably more than 50 mol%, in particular more than 70 mol% and especially at least 80 mol% such as 90 to 95 mole%.
  • the proportion of monomers B2), if present, is preferably less than 80 mol%, in particular less than 50 mol% and especially at less than 20 mol% such as 2 to 10 mol% of the Total amount of monomers B1) and B2).
  • Particularly preferred are the Polymers B) only from the monomers B1) and, if appropriate, B2), which then become Add 100 mol%.
  • Preferred monomers of the copolymers B) are esters of acrylic acid, methacrylic acid, Maleic acid, fumaric acid and itaconic acid with octanol, nonanol, decanol, undecanol, Dodecanol, n-tridecanol, iso-tridecanol, tetradecanol, pentadecanol, hexadecanol and their mixtures.
  • Preferred monomers are also amides and optionally imides of these acids with octylamine, nonylamine, decylamine, Undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, Hexadecylamine and mixtures thereof.
  • the copolymers containing component B Comonomers which esters and / or ethers of ethylenically unsaturated Alcohols having 2 to 10 carbon atoms, and carboxylic acids or alcohols, which Are carrying alkyl radicals having 8 to 16 carbon atoms.
  • Such preferred monomers of the copolymers B) are, for example, esters of Vinyl alcohol with octanoic acid, 2-ethylhexanoic acid, nonanoic acid, neononanoic acid, Decanoic acid, neodecanoic acid, undecanoic acid, neoundecanoic acid, dodecanoic acid, Tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid and their Mixtures.
  • Further preferred monomers of the copolymers B) are, for example, ethers of allyl especially the vinyl alcohol with octanol, nonanol, decanol, undecanol, Dodecanol, n-tridecanol, iso-tridecanol, tetradecanol, pentadecanol, hexadecanol and their mixtures.
  • comonomers B2 are also olefins having 10-20 carbon atoms, preferably with 12-18 C atoms and in particular with 10-16 C atoms suitable. This is it preferably linear ⁇ -olefins with terminal double bond.
  • branched olefins such as in particular Oligomers of isobutylene and propylene with 10 to 20 carbon atoms.
  • alkyl (meth) acrylates alkyl (meth) acrylates, alkyl vinyl esters, alkyl vinyl ethers having 1 to 5 C atoms in the alkyl radical and ethylenically unsaturated free carboxylic acids
  • acrylic acid methacrylic acid, maleic acid, fumaric acid, itaconic acid and functional groups such as -OH, -SH, -N-, -CN-bearing monomers
  • -OH, -SH, -N-, -CN-bearing monomers can be used in minor amounts of up to 20 mol%, preferably ⁇ 10 mol%, especially ⁇ 5 mol% may also be present in the copolymers B.
  • subordinate Amounts of up to 20 mole% preferably ⁇ 10 mole%, especially ⁇ 5 mole% may also be used be further comonomers containing those with the monomers mentioned copolymerizable, e.g. Allyl polyglycol ethers, vinyl aromatics and higher molecular weight olefins such as poly (isobutylene).
  • the polymers of the invention can be prepared by direct polymerization from the mentioned monomers in known polymerization processes such as bulk, solution, Emulsion, suspension or precipitation polymerization are prepared.
  • esters may also be obtained by derivatization of e.g. Acid or hydroxyl groups carrying base polymer with corresponding fatty acids, fatty alcohols or Fettamines be prepared with 8 to 16 carbon atoms in the alkyl radical.
  • the esterifications, Etherifications, amidations and / or imidations are carried out according to known methods Condensation process.
  • the derivatization may be complete or partial.
  • Partially esterified or amidated, acid-based polymers have (solvent-free) preferably acid numbers of 60-140 mg KOH / g and in particular of 80- 120 mg KOH / g.
  • Copolymers with acid numbers of less than 80, especially less than 60 mg KOH / g are considered to be fully derivatized.
  • Partially esterified or etherified hydroxyl-bearing polymers have OH numbers of 40 to 200 mg KOH / g, preferably 60 to 150 mg KOH / g; Copolymers with hydroxyl numbers of less as 60 and especially less than 40 mg KOH / g are considered to be fully derivatized considered. Particularly preferred are partially derivatized polymers.
  • suitable acid group-bearing polymers are homo- and copolymers ethylenic unsaturated carboxylic acids such as acrylic acid, methacrylic acid, Maleic acid, fumaric acid, itaconic acid or their reactive equivalents such as lower ones Esters or anhydrides such as methyl methacrylate and Maleic anhydride with each other as well as with others with these acids copolymerizable monomers.
  • suitable examples are poly (acrylic acid), Poly (methacrylic acid), poly (maleic acid), poly (maleic anhydride), poly (acrylic acid-co-maleic acid).
  • Suitable fatty alcohols and fatty amines are especially linear, but they can also minor amounts, z. B. up to 30 wt .-%, preferably up to 20 wt .-% and specifically contain up to 10 wt .-% of branched alkyl radicals.
  • the branches are located preferably in the 1- or 2-position. Shorter as well as longer-chain fatty alcohols or Fatty amines can be used, but their proportion is preferably below 20 mol% and especially less than 10 mol%, such as between 1 and 5 mol% based on the total amount of amines used.
  • Particularly preferred fatty alcohols are octanol, decanol, undecanol, dodecanol, Tridecanol, tetradecanol, pentadecanol and hexadecanol.
  • Suitable amines are primary and secondary amines having one or two C 8 -C 16 alkyl radicals. They can carry one, two or three amino groups which are linked via alkylene radicals having two or three carbon atoms. Preference is given to monoamines.
  • primary amines are octylamine, 2-ethylhexylamine, decylamine, undecylamine, dodecylamine, n-tridecylamine, iso-tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine and mixtures thereof.
  • Preferred secondary amines are dioctylamine, dinonylamine, didecylamine, didodecylamine, ditetradecylamine, dihexadecylamine, and amines having different alkyl chain lengths such as N-octyl-N-decylamine, N-decyl-N-dodecylamine, N-decyl-N-tetradecylamine, N-decyl N-hexadecylamine, N-dodecyl-N-tetradecylamine, N-dodecyl-N-hexadecylamine, N-tetradecyl-N-hexadecylamine.
  • Secondary amines which, in addition to a C 8 -C 16 -alkyl radical, bear shorter side chains having 1 to 5 C atoms, for example methyl or ethyl groups, are suitable according to the invention.
  • the alkyl chain length n is taken into account as the mean value of the alkyl chain lengths of C 8 to C 16 for the calculation of the Q factor.
  • Shorter and longer alkyl radicals, if present, are not included in the calculation because they do not contribute to the effectiveness of the additives. Therefore, the proportion of shorter and longer alkyl chains is preferably less than 20 mol%, preferably less than 10 mol%, based on the total amount of amine used.
  • Particularly preferred are amides derived from primary monoamines and imides.
  • hydroxyl-bearing polymers are homo- and Copolymers of hydroxyl-bearing monomers such as vinyl alcohol, allyl alcohol or also hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and Hydroxypropyl methacrylate.
  • Suitable fatty acids have 8 to 16 carbon atoms in the Alkyl.
  • the alkyl radical is essentially linear but may also be secondary Amounts, for example, up to 30% by weight, preferably up to 20% by weight and especially up to Contain 10 wt .-% of branched isomers.
  • nonanoic acid Decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, Pentadecanoic acid, hexadecanoic acid, heptadecanoic acid and octadecanoic acid and Nonadecanoic acid and mixtures thereof.
  • esterification, etherification, amidation or imidation can increase the effectiveness of additives according to the invention further to special fatty acid ester compositions be adjusted.
  • the molecular weights of the copolymers B according to the invention are between 1,000 and 100,000, in particular between 2,000 and 50,000 and in particular between 2,500 and 25,000 g / mol, measured by gel permeation chromatography (GPC) against poly (styrene).
  • Copolymers of the invention B must be in practice-relevant Dosing be oil-soluble, that is, they must be in the oil to be added dissolve residue-free at 50 ° C.
  • mixtures of the invention Copolymers B provided that the average of the R values of the Mixture components in turn values from 11.0 to 14.0, preferably from 11.5 to 13.5 and in particular assumes values of 12.0 to 13.0.
  • the mixing ratio of the additives A and B according to the invention is (in Parts by weight) 20: 1 to 1:20, preferably 10: 1 1 to 1:10, in particular 5: 1 to 1: 2.
  • the additives according to the invention are oils in amounts of from 0.001 to 5% by weight, preferably 0.005 to 1 wt .-% and especially added 0.01 to 0.5 wt .-%. there they may be dissolved as such or dissolved in solvents, e.g. aliphatic and / or aromatic hydrocarbons or Hydrocarbon mixtures such as e.g.
  • the additives according to the invention preferably contain 1-80%, especially 10 - 70%, in particular 25 - 60% solvent.
  • the fuel oil is F2, the often referred to as “biodiesel”, “biofuel or” biofuel “to Fatty acid alkyl esters of fatty acids having 12 to 24 carbon atoms and alcohols having 1 to 4 carbon atoms. Usually a major part of the fatty acids contains one, two or three Double bonds.
  • oils F2 derived from animal or vegetable material examples include rapeseed oil, coriander oil, soybean oil, Cottonseed oil, sunflower oil, castor oil, olive oil, peanut oil, corn oil, almond oil, Palm kernel oil, coconut oil, mustard seed oil, beef tallow, bone oil, fish oils and used cooking oils.
  • oils derived from wheat, jute, Sesame, Scheabaumnuß, Arachisöl and linseed oil derive can from these oils according to the prior art derived from known methods.
  • Rapeseed oil containing a mixture of glycerin is partially esterified fatty acids is preferred because it is available in large quantities and is readily available by squeezing rapeseed. Furthermore are the also widespread oils of sunflower and soy and their Mixtures with rapeseed oil are preferred.
  • biofuels F2 are lower alkyl esters of fatty acids.
  • commercial mixtures of ethyl, propyl, butyl and in particular methyl esters of fatty acids having 14 to 22 carbon atoms for example, lauric acid, myristic acid, palmitic acid, palmitoleic acid, Stearic acid, oleic acid, elaidic acid, petroselinic acid, ricinoleic acid, elaeostearic acid, Linoleic acid, linolenic acid, eicosanoic acid, gadoleic acid, docosanoic acid or Erucic acid, which preferably has an iodine value of 50 to 150, in particular 90 to 125 have.
  • Mixtures with particularly advantageous properties are those which mainly, d. H. at least 50% by weight, methyl esters of fatty acids with 16 to Contain 22 carbon atoms and 1, 2 or 3 double bonds.
  • the preferred ones lower alkyl esters of fatty acids are the methyl esters of oleic acid, linoleic acid, Linolenic acid and erucic acid.
  • a biofuel is an oil derived from vegetable or animal material or is obtained or a derivative thereof, which as fuel and especially as diesel or heating oil can be used.
  • vegetable oil derivatives are preferred, particularly preferred biofuels alkyl ester derivatives of rapeseed oil, Cottonseed oil, soybean oil, sunflower oil, olive oil or palm oil are, being Rapsölchuremethylester, sunflower oil and Sojaölchuremethylester are very particularly preferred.
  • biofuel or as a component in biofuel are also used grease esters such as used fat methyl ester.
  • mineral oil component F1 in particular middle distillates are suitable, by Crude oil distillation and boiling in the range of 120 to 450 ° C, For example, kerosene, jet fuel, diesel and heating oil.
  • Middle distillates used, the 0.05 wt .-% sulfur and less, especially preferably less than 350 ppm sulfur, in particular less than 200 ppm sulfur and in special cases less than 50 ppm of sulfur, such as less than Contain 10 ppm of sulfur.
  • These are generally such Middle distillates which have been subjected to a hydrogenating refining, and therefore contain only low levels of polyaromatic and polar compounds.
  • middle distillates Preferably, these are middle distillates, the 95% distillation points below 370 ° C, in particular 350 ° C and in special cases below 330 ° C.
  • synthetic fuel as for example according to the Fischer-Tropsch process are accessible, are suitable as middle distillates.
  • the additive may be added to the oil to be treated according to art known in the art Method be supplied. If more than one additive component or Coadditive component should be used, such components may be together or separately in any combination and order into the oil.
  • the additives according to the invention allow the CFPP value of mixtures to be determined Improve biodiesel and mineral oils much more efficiently than with known additives of the prior art.
  • the additives according to the invention are particularly advantageous in Oil mixtures whose mineral oil component F1) has a boiling width between the 20 and 90% distillation point of less than 120 ° C, especially less than 110 ° C. and especially less than 100 ° C.
  • they are special advantageous in oil mixtures whose mineral oil component F1) has a cloud point of below -4 ° C, especially from -6 ° C to -20 ° C such as from -7 ° C to -9 ° C has, as they are used for use especially in winter.
  • the additives of the invention are particularly advantageous in oil mixtures containing more than 2% by volume of biofuel F 2, preferably more than 5% by volume of biofuel F 2 and especially more than 10% by volume Biofuel F2 such as 15 to 35 vol .-% biofuel F2 included.
  • the additives according to the invention are particularly advantageous in problematic oils whose biofuel component F2 has a high content Saturated fatty acid esters of more than 4%, in particular more than 5% and specifically from 7 to 25%, such as from 8 to 20%, such as for example in oils from sunflower and soy is the case.
  • Such biofuels have prefers a cloud point above -5 ° C and especially above -3 ° C.
  • Oil mixtures F) in which the additives according to the invention are particularly advantageous Have cloud points above -9 ° C and especially over - 6 ° C. It is thus also possible with the additives according to the invention Rapsölklaremethylester and sunflower and / or soybean oil fatty acid methyl ester to adjust the oil mixtures to CFPP values of -22 ° C and below.
  • the additives according to the invention also together with one or more oil-soluble co-additives be used, which already by itself the cold flow properties of Improve crude oils, lubricating oils or fuel oils.
  • oil-soluble co-additives are polar compounds which differ from the polymers B according to the invention and which cause a paraffin dispersion (paraffin dispersants), Alkylphenol condensates, esters and ethers of polyoxyalkylene compounds, Olefin copolymers and oil-soluble amphiphiles.
  • the additives according to the invention can be used to further reduce the Sedimentation in the cold precipitated paraffins and fatty acid esters in mixture with Paraffin dispersants are used.
  • Paraffin dispersants reduce the size the paraffin and fatty acid ester crystals and cause the paraffin particles to do not settle, but colloidally with significantly reduced Sedimentationsbestreben, remain dispersed.
  • As paraffin dispersants both low molecular weight and also polymeric, oil-soluble compounds having ionic or polar groups, e.g. Amine salts and / or amides proven.
  • paraffin dispersants contain reaction products of fatty amines with alkyl radicals having 18 to 24 C atoms, especially with secondary fatty amines such as ditallow fatty amine, distearylamine and Dibehenylamine with carboxylic acids and their derivatives.
  • secondary fatty amines such as ditallow fatty amine, distearylamine and Dibehenylamine with carboxylic acids and their derivatives.
  • Paraffin dispersants obtained by reaction of aliphatic or aromatic amines, preferably long-chain aliphatic amines, with aliphatic or aromatic Mono-, di-, tri- or tetracarboxylic acids or their anhydrides are obtained (see. US 4 211 534).
  • amides and ammonium salts of Aminoalkylenpolycarbon Acid such as nitrilotriacetic acid or Ethylenediaminetetraacetic acid with secondary amines as paraffin dispersants suitable (see EP 0 398 101).
  • paraffin dispersants are copolymers of the Maleic anhydride and ⁇ , ⁇ -unsaturated compounds, optionally with primary monoalkylamines and / or aliphatic alcohols are reacted can (see EP 0 154 177) and the reaction products of Alkenylspirobislactonen with amines (compare EP-0 413 279 B1) and according to EP-A-0 606 055 A2 reaction products of terpolymers based on ⁇ , ⁇ -unsaturated dicarboxylic acid anhydrides, ⁇ , ⁇ -unsaturated Compounds and polyoxyalkylene ethers of lower unsaturated alcohols.
  • Alkylphenol-aldehyde resins are, for example, in Römpp Chemie Lexikon, 9th edition, Thieme Verlag 1988-92, Volume 4, p 3351 et seq described.
  • the alkyl radicals of the o- or p-alkylphenol can be used in the case of the additives according to the invention
  • Alkylphenol-aldehyde resins may be the same or different and have 1-50, preferably 1 to 20, in particular 4 to 12, carbon atoms; it is preferable to n-, iso- and tert-butyl, n- and iso-pentyl, n- and iso-hexyl, n- and iso-octyl, n- and iso-nonyl, n- and iso-decyl, n- and iso-dodecyl and octadecyl.
  • the aliphatic Aldehyde in the alkylphenol-aldehyde resin preferably has 1 to 4 carbon atoms.
  • Particularly preferred aldehydes are formaldehyde, acetaldehyde and butyraldehyde, especially formaldehyde.
  • the molecular weight of the alkylphenol-aldehyde resins is 400-10,000, preferably 400-5000 g / mol. Prerequisite here is that the Resins are oil soluble.
  • these alkylphenol-formaldehyde resins are those which are oligomers or polymers having a repeating structural unit of the formula wherein R 5 is C 1 -C 50 alkyl or alkenyl and n is a number from 2 to 100.
  • R 5 is preferably C 4 -C 20 -alkyl or -alkenyl and in particular C 6 -C 16 -alkyl or -alkenyl.
  • n is a number from 4 to 50 and especially from 5 to 25.
  • Suitable flow improvers are polyoxyalkylene compounds such as For example, esters, ethers and ethers / esters containing at least one alkyl radical with 12 bis Wear 30 C atoms.
  • esters, ethers and ethers / esters containing at least one alkyl radical with 12 bis Wear 30 C atoms.
  • the alkyl groups are derived from an acid, the Remainder of a polyhydric alcohol; the alkyl radicals come from a fatty alcohol, so the rest of the compound is from a polyacid.
  • Suitable polyols are polyethylene glycols, polypropylene glycols, polybutylene glycols and their copolymers having a molecular weight of about 100 to about 5000, preferably 200 to 2000.
  • alkoxylates of polyols such as for example, glycerol, trimethylolpropane, pentaerythritol, neopentyl glycol, as well as the oligomers obtainable therefrom by condensation with 2 to 10 Monomer units, e.g. Polyglycerol.
  • Preferred alkoxylates are those of 1 to 100, in particular 5 to 50 moles of ethylene oxide, propylene oxide and / or butylene oxide per mole Polyol. Esters are especially preferred.
  • Fatty acids containing 12 to 26 carbon atoms are preferred for reaction with the polyols to form the ester additives, preferably using C 18 to C 24 fatty acids, especially stearic and behenic acid.
  • the esters can also be prepared by esterification of polyoxyalkylated alcohols. Preference is given to completely esterified polyoxyalkylated polyols having molecular weights of 150 to 2,000, preferably 200 to 1,500. Particularly suitable are PEG-600 dibehenate and glycerol-ethylene glycol tribehenate.
  • Suitable olefin polymers as part of the additive according to the invention may be derived directly from monoethylenically unsaturated monomers or indirectly by Hydrogenation of polymers derived from polyunsaturated monomers such as Isoprene or butadiene derived, are produced.
  • Preferred copolymers contain in addition to ethylene structural units derived from ⁇ -olefins having 3 to 24 carbon atoms and have molecular weights of up to 120,000.
  • Preferred ⁇ -olefins are Propylene, butene, isobutene, n-hexene, isohexene, n-octene, isooctene, n-decene, isodecene.
  • the comonomer content of olefins is preferably between 15 and 50 mol%, more preferably between 20 and 35 mole% and especially between 30 and 45 mole%. These copolymers can also be minor amounts, e.g. up to 10 mol% more Comonomers such as e.g. non-terminal olefins or non-conjugated olefins contain. Preferred are ethylene-propylene copolymers.
  • the olefin copolymers can prepared by known methods, e.g. by Ziegler or metallocene catalysts.
  • olefin copolymers are block copolymers containing blocks of olefinically unsaturated aromatic monomers A and blocks of hydrogenated polyolefins B.
  • Particularly suitable are block copolymers of the structure (AB) n A and (AB) m , where n is a number between 1 and 10 and m is a number between 2 and 10.
  • the mixing ratio (in parts by weight) of the additives according to the invention Paraffin dispersants, comb polymers, alkylphenol condensates, Each of polyoxyalkylene derivatives and olefin copolymers is 1:10 to 20: 1, preferably 1: 1 to 10: 1, such as 1: 1 to 4: 1.
  • the additives can be used alone or together with other additives be, e.g. with other pour point depressants or dewaxing aids, with Antioxidants, cetane improvers, dehazers, demulsifiers, detergents, Dispersants, defoamers, dyes, corrosion inhibitors, Conductivity improvers, sludge inhibitors, odorants and / or additives to Humiliation of the cloud point.
  • other pour point depressants or dewaxing aids with Antioxidants, cetane improvers, dehazers, demulsifiers, detergents, Dispersants, defoamers, dyes, corrosion inhibitors, Conductivity improvers, sludge inhibitors, odorants and / or additives to Humiliation of the cloud point.
  • the ethylene copolymers used are commercial products having the characteristics given in Table 4. The products were used as 65% settings in kerosene. Characterization of the ethylene copolymers (A) used example Comonomer (s) V140 CH 3 / 100CH 2 A1 13.6 mole% vinyl acetate 130 mPas 3.7 A2 13.7 mole percent vinyl acetate and 1.4 mole percent vinyl neodecanoate 105 mPas 5.3 A3 i) 14.0 mol% vinyl acetate and 1.6 mol% vinyl neodecanoate and ii) 12.9 mol% of vinyl acetate in the ratio i): ii) of 6: 1 97 mPas 145 mPas 4.7 5.4
  • the further flow improvers used C are commercial products with the characteristics given in Table 6. The products were used as 50% settings in solvent naphtha. Characterization of the further flow improvers used C3 Reaction product of a copolymer of C 14 / C 16 olefin and maleic anhydride with 2 equivalents of secondary tallow fatty amine per maleic anhydride unit C4 Reaction product of phthalic anhydride with 2 equivalents of di (hydrogenated tallow fatty amine) to the amide ammonium salt C5
  • Nonylphenol resin prepared by condensing a mixture of dodecylphenol with formaldehyde, Mw 2000 g / mol C6 Mixture of 2 parts C3 and 1 part C5 C7 Mixture of equal parts C4 and C5
  • the CFPP value (according to EN 116, in ° C) of various biofuels according to the above table was determined after addition of 1200 ppm, 1500 ppm and 2000 ppm of additive mixture. Percentages refer to parts by weight in the respective mixtures.
  • the results presented in Tables 5 to 7 show that comb polymers with the factor Q according to the invention achieve excellent CFPP reductions even at low dosing rates and offer additional potential at higher dosing rates.
  • flow improvers Comb polymer / coadditive CFPP after addition of flow improver 50 ppm 100 ppm 150 ppm 200ppm 1 A2 150 ppm B4 -13 -18 -19 -20 2 A1 100 ppm B6 -17 -20 -19 -21 3 A2 150 ppm B2 -18 -20 -22 -22 4 A2 150 ppm B1 -19 -21 -21 -23 5 A1 100 ppm B7 -20 -20 -22 -23 6 A1 150 ppm B5 -19 -21 -20 -22 7 A2 150 ppm B3 -16 -18 -19 -21 8th A2 75 ppm B7 75 ppm A4 -19 -22 -23 -25 9 (Cf.) A2 150 ppm B8 -11 -14 -16 -17 10 (Cf.) A2 150 ppm B9 -9 -10 -13 -16 11 (Cf.) A2 150 ppm B10 -10 -11 -15 -20 13 (Cf
  • Ethylene copolymer comb polymer co-additive CFPP 100 ppm 150 ppm 200 ppm 300 ppm 14 80% A3 20% B4 150 ppm C6 -18 -20 -22 -24 15 80% A3 20% B6 150 ppm C6 -20 -21 -24 -25 16 80% A3 20% B2 150 ppm C6 -20 -21 -23 -26 17 80% A3 20% B1 150 ppm C6 -21 -22 -25 -27 18 75% A3 25% B7 150 ppm C6 -20 -20 -23 -26 19 85% A1 15% B5 150 ppm C6 -20 -22 -24 -27 20 80% A1 20% B3 150 ppm C7 -19 -21 -23 -25 21 (Cf.) 80% A3 20% B8 150 ppm C6 -17 -18 -19 -21 22 (See) 80% A1 20% B9 150 ppm C6 -11 -16 -19 -19 23 (Cf.

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EP04028307.9A 2003-12-11 2004-11-30 Huiles combustibles comprenant des distillats moyens et des huiles d'origine végétale ou animale et ayant des propriétés à froid améliorées Active EP1541663B1 (fr)

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US7473284B2 (en) 2009-01-06
CA2490031A1 (fr) 2005-06-11
EP1541663B1 (fr) 2016-01-20
KR20050058217A (ko) 2005-06-16
PL1541663T3 (pl) 2016-07-29
DE10357878B4 (de) 2008-05-29
DE10357878A1 (de) 2005-07-28
JP2005200637A (ja) 2005-07-28
CA2490031C (fr) 2013-07-09
KR101136333B1 (ko) 2012-04-23
DE10357878C5 (de) 2013-07-25
US20050126070A1 (en) 2005-06-16
HUE028480T2 (en) 2016-12-28

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