EP1209215B1 - Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant - Google Patents

Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant Download PDF

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Publication number
EP1209215B1
EP1209215B1 EP01126254A EP01126254A EP1209215B1 EP 1209215 B1 EP1209215 B1 EP 1209215B1 EP 01126254 A EP01126254 A EP 01126254A EP 01126254 A EP01126254 A EP 01126254A EP 1209215 B1 EP1209215 B1 EP 1209215B1
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mol
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EP01126254A
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German (de)
English (en)
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EP1209215A3 (fr
EP1209215A2 (fr
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Matthias Dr. Krull
Werner Dr. Reimann
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Clariant Produkte Deutschland GmbH
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Clariant Produkte Deutschland GmbH
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Application filed by Clariant Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Priority to EP07005870A priority Critical patent/EP1803791B1/fr
Priority to EP07005871A priority patent/EP1801188B1/fr
Publication of EP1209215A2 publication Critical patent/EP1209215A2/fr
Publication of EP1209215A3 publication Critical patent/EP1209215A3/fr
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    • 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)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • the present invention relates to mixtures of fatty acids and paraffin dispersants having improved low-temperature stability, and to their use for improving the lubricity of middle distillate fuel oils.
  • Mineral oils and mineral oil distillates used as fuel oils generally contain 0.5% by weight and more sulfur which causes the formation of sulfur dioxide upon combustion. In order to reduce the resulting environmental impact, the sulfur content of fuel oils is lowered further and further.
  • the standard EN 590 relating to diesel fuels currently prescribes a maximum sulfur content of 350 ppm in Germany. In Scandinavia fuel oils of less than 50 ppm and in exceptional cases less than 10 ppm of sulfur are used. These fuel oils are usually prepared by hydrogenating the fractions obtained from the petroleum by distillation. In the desulfurization but other substances are removed, which give the fuel oils a natural lubricating effect. These substances include polyaromatic and polar compounds.
  • EP-A-0 798 364 discloses salts and amides of mono- to tetracarboxylic acids having 2 to 50 carbon atoms and aliphatic mono- / polyamines having 2 to 50 carbon atoms and 1 to 10 N atoms as lubricity additives for low-sulfur diesel fuel.
  • Preferred amines have 8-20 C-atoms, such as coco fatty amine, tallow fatty amine and oleylamine.
  • WO 95/33805 discloses the use of cold flow improvers to improve the lubricity of low sulfur middle distillates.
  • polar nitrogen-containing compounds which contain a group NR 13 , where R 13 is a hydrocarbon radical having 8 to 40 C atoms and may be present in the form of a cation.
  • WO-A-96/18706 disclosed in analogy to WO 95/33805 the use of the nitrogen-containing compounds mentioned therein in combination with lubricity additives.
  • WO-A-96/23855 disclosed in analogy to WO 95/33805 the use of the nitrogen-containing compounds mentioned therein in combination with detergent additives.
  • the fatty acids used in the prior art have the disadvantage that they solidify when stored at low temperatures, ie often at room temperature, usually at temperatures of 0 ° C at -5 ° C at the latest, or that deposit crystalline particles and problems prepare handling. This problem can only be partially solved by dilution with organic solvents, since components also crystallize out of these solutions or the solution gels and solidifies. For use as lubricity additives, they therefore have to be diluted considerably, or kept in heated storage containers and metered via heated lines.
  • the object underlying the present invention was to find lubricity additives which improve the lubricating effect of middle distillates at reduced metering rates, but remain homogeneous, clear and, in particular, free-flowing even in the cold.
  • Another object of the invention are cold-stabilized solutions of the additives of the invention in organic solvents, wherein the solutions contain 1 to 80 wt .-% of solvent.
  • Suitable solvents are aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures.
  • the additives according to the invention preferably contain from 10 to 70%, in particular from 25 to 60% of solvent.
  • the cold-stabilized solutions according to the invention have a pour point of below -40 ° C., preferably -45 ° C., especially -50 ° C.
  • Another object of the invention is the use of said mixtures of the components A and B to improve the lubricating properties of low-sulfur middle distillates with up to 0.05 wt .-% sulfur content.
  • Preferred fatty acids are those having 8-40 C atoms, in particular 12-22 C atoms.
  • the alkyl radicals of the fatty acids consist essentially of carbon and hydrogen. However, they may contain other substituents, e.g. Hydroxyl, halogen, amino or nitro groups, provided they do not affect the predominantly hydrocarbon character.
  • Component A2) may contain one or more double bonds and be of natural or synthetic origin. In the case of polyunsaturated carboxylic acids, their double bonds may be isolated or else conjugated.
  • the proportion of saturated fatty acids A1) in the mixture of A1) and A2) is preferably below 20% by weight, in particular below 10% by weight, especially below 5% by weight.
  • preferred fatty acid mixtures, which here the combination of A1) and A2) understood is at least 50 wt .-%, in particular at least 75 wt .-%, especially at least 90 wt .-% of the constituents one or more double bonds.
  • These preferred fatty acid (mixtures) have iodine numbers of at least 40 gl / 100 g, preferably at least 80 gl / 100 g, in particular at least 125 gl / 100 g.
  • Suitable fatty acids are, for example, lauric, tridecane, myristic, pentadecane, palmitic, margarine, stearic, isostearic, arachic and behenic acid, oleic and erucic acid, palmitoleic, myristoleic, linoleic, linolenic, elaeosterol - And arachidonic acid, ricinoleic acid and derived from natural fats and oils fatty acid mixtures, such as Coconut oil, peanut oil, fish, linseed oil, palm oil, rapeseed oil, ricinine, castor oil, rapeseed oil, soybean oil, sunflower oil and tall oil fatty acid.
  • dicarboxylic acids such as dimer fatty acids and alkyl- and alkenylsuccinic acids with C 8 -C 50 -alk (en) yl radicals, preferably with C 8 -C 40 -, in particular with C 12 -C 22 -alkyl radicals.
  • the alkyl radicals can be linear or branched (oligomerized alkenes, PIB).
  • the fatty acids may further contain 1-40, especially 1-25% by weight of resin acids, based on the weight of A1) and A2) together.
  • the additives according to the invention contain as component B at least one polar nitrogen-containing compound which is effective as paraffin dispersant in middle distillates.
  • Paraffin dispersants reduce the size of paraffin crystals precipitated in the cold and cause the paraffin particles not to settle but to remain colloidally dispersed with significantly reduced sedimentation effort.
  • alkyl, cycloalkyl and aryl radicals may optionally be substituted.
  • Suitable substituents of the alkyl and aryl radicals are, for example, (C 1 -C 6 ) -alkyl, halogens, such as fluorine, chlorine, bromine and iodine, preferably chlorine and (C 1 -C 6 ) -alkoxy.
  • Alkyl here stands for a straight-chain or branched hydrocarbon radical. Specific examples which may be mentioned are: n-butyl, tert-butyl, n-hexyl, n-octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, dodecenyl, tetrapropenyl, tetradecenyl, pentapropenyl, hexadecenyl, octadecenyl and eicosanyl or mixtures such as cocoalkyl , Tallow fatty alkyl and behenyl.
  • Cycloalkyl here stands for a cyclic aliphatic radical with 5-20 Carbon atoms.
  • Preferred cycloalkyl radicals are cyclopentyl and cyclohexyl.
  • Aryl here stands for an optionally substituted aromatic ring system having 6 to 18 carbon atoms.
  • the terpolymers consist of the bivalent structural units of the formulas 12 and 14 and 15 and 16 and optionally 13. They contain only in a conventional manner the end groups formed in the polymerization by initiation, inhibition and chain termination.
  • structural units of the formulas 12 to 14 are derived from ⁇ , ⁇ -unsaturated dicarboxylic acid anhydrides of the formulas 17 and 18 such as maleic anhydride, itaconic anhydride, citraconic anhydride, preferably maleic anhydride.
  • the structural units of the formula 15 are derived from the ⁇ , ⁇ -unsaturated compounds of the formula 19.
  • the structural units of formula 16 are derived from polyoxyalkylene ethers of lower, unsaturated alcohols of formula 20.
  • ⁇ -olefin oxides such as ethylene oxide, propylene oxide and / or butylene oxide
  • polymerizable lower unsaturated alcohols are, for example, allyl alcohol, methallyl alcohol, butenols, such as 3-buten-1-ol and 1-buten-3-ol or methylbutenols, such as 2-methyl-3-buten-1-ol, 2-methyl-3 -but-2-ol and 3-methyl-3-buten-1-ol.
  • Preferred are addition products of ethylene oxide and / or propylene oxide with allyl alcohol.
  • etherification products of the polyoxyalkylene ethers can also be prepared by reacting ⁇ -olefin oxides, preferably ethylene oxide, propylene oxide and / or butylene oxide, with alcohols of the formula 22 R 32 - OH (22) wherein R 32 is equal to C 1 -C 24 alkyl, C 5 -C 20 cycloalkyl or C 6 -C 18 aryl, by known methods attached and with polymerizable lower unsaturated halides of the formula 23rd where W is a halogen atom.
  • the halides used are preferably the chlorides and bromides. Suitable production methods are mentioned, for example, in J. March, Advanced Organic Chemistry, 2nd Edition, p. 377f (1977).
  • the esterification of the polyoxyalkylene ethers takes place by reaction with customary esterification agents, such as carboxylic acids, carboxylic acid halides, carboxylic anhydrides or carboxylic acid esters with C 1 -C 4 -alcohols.
  • esterification agents such as carboxylic acids, carboxylic acid halides, carboxylic anhydrides or carboxylic acid esters with C 1 -C 4 -alcohols.
  • the halides and anhydrides of C 1 -C 40 -alkyl, C 5 -C 10 -cycloalkyl or C 6 -C 18 -arylcarboxylic acids are preferred used.
  • the esterification is generally carried out at temperatures of 0 to 200 ° C, preferably 10 to 100 ° C.
  • the index m indicates the degree of alkoxylation, i. the number of moles of ⁇ -olefin, which are added per mole of formula 20 or 21.
  • Suitable secondary amines for preparing the terpolymers are: didecylamine, ditetradecylamine, distearylamine, dicocosfettamine, ditallow fatty amine and mixtures thereof.
  • the terpolymers have K values (measured according to Ubbelohde in 5% strength by weight solution in toluene at 25 ° C.) of 8 to 100, preferably 8 to 50, corresponding to average molecular weights (M w ) of between about 500 and 100,000. Suitable examples are in EP 606,055 listed.
  • the mixing ratio between A and B can vary within wide limits. Thus, even small amounts of B from 100 ppm to 50,000 ppm, preferably 1,000 ppm to 10,000 ppm, in fatty acid solutions as a cold additive for A. They are able to prevent self-crystallization of the fatty acid, which leads to a lowering of the cloud point, or sedimentation Prevent formed crystals and thus allow easy handling at reduced temperatures. However, for specific problem solutions, from 5% up to 50%, in special cases up to 90% of constituent B, based on the amount of constituent A, may also be present. In particular, the self-sticking point of the additive is lowered and the lubricity of the additized oil is improved. Consequently, the preferred mixing ratio of A: B is between 1:10 and 1: 0.0001, in particular between 1: 4 and 1: 0.0005, especially between 1: 1 and 1: 0.001.
  • the additives according to the invention are added to oils in amounts of from 0.001 to 0.5% by weight, preferably from 0.001 to 0.1% by weight. They may be used as such or dissolved in solvents, such as aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures such as toluene, xylene, ethylbenzene, decane, pentadecane, gasoline fractions, kerosene or commercial solvent mixtures such as Solvent Naphtha, ® Shellsol AB, ® Solvesso 150 , ® Solvesso 200, ® Exxsol, ® Isopar and ® Shellsol D types.
  • solvents such as aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures such as toluene, xylene, ethylbenzene, decane, pentadecane, gasoline fractions, kerosene or commercial solvent mixtures such as Solvent Naphtha, ® Shellsol
  • the additives according to the invention preferably contain 1 to 80%, especially 10 to 70%, in particular 25 to 60%, of solvent.
  • the additives which can be used without problems even at low temperatures of, for example, -40 ° C and lower, improve the lubricity of the additized oils and their cold and corrosion protection properties.
  • the additives according to the invention can also be used together with one or more oil-soluble co-additives, which in themselves improve the cold flow properties and / or lubricity of crude oils, lubricating oils or fuel oils.
  • oil-soluble co-additives are vinyl acetate-containing copolymers or terpolymers of ethylene, comb polymers, alkylphenol-aldehyde resins and oil-soluble amphiphiles.
  • the additives according to the invention are used in admixture with ethylene / vinyl acetate / vinyl neononanoate terpolymers or ethylene / vinyl acetate / vinyl neodecanoate terpolymers to improve the flowability of mineral oils or mineral oil distillates.
  • the terpolymers of vinyl neononanoate or vinyl neodecanoate contain, in addition to ethylene, 10 to 35% by weight of vinyl acetate and 1 to 25% by weight of the respective neo compound.
  • copolymers contain besides ethylene and 10 to 35% by weight of vinyl esters or from 0.5 to 20% by weight of olefins such as diisobutylene, 4-methylpentene or norbornene.
  • the mixing ratio of the additives according to the invention with the ethylene-vinyl acetate copolymers described above or the terpolymers of ethylene, vinyl acetate and the vinyl esters of neononanic or neodecanoic acid is (in parts by weight) 20: 1 to 1:20, preferably 10: 1 to 1: 10th
  • these alkylphenol-formaldehyde resins are those of the formula in which R 51 is C 4 -C 50 -alkyl or -alkenyl, R 50 is ethoxy- and / or propoxy, n is a number from 5 to 100 and p is a number from 0 to 50.
  • the additives according to the invention are used together with comb polymers.
  • This term refers to polymers in which hydrocarbon radicals having at least 8, in particular at least 10, carbon atoms are bonded to a polymer backbone.
  • they are homopolymers whose alkyl side chains contain at least 8 and in particular at least 10 carbon atoms.
  • at least 20%, preferably at least 30% of the monomers have side chains (cf. Comb-like Polymers-Structure and Properties; NA Platé and VP Shibaev, J. Polym. Sci. Macromolecular Revs. 1974, 8, 117 ff ).
  • Suitable comb polymers are, for example, fumarate / vinyl acetate copolymers (cf. EP 0 153 176 A1 ), Copolymers of a C 6 -C 24 ⁇ -olefin and a NC 6 -C 22 -alkylmaleimide (cf. EP 0 320 766 Further, esterified olefin / maleic anhydride copolymers, polymers and copolymers of ⁇ -olefins and esterified copolymers of styrene and maleic anhydride.
  • the mixing ratio (in parts by weight) of the inventive additives with resins or comb polymers is 1:10 to 20: 1, preferably 1: 1 to 10: 1.
  • the additives according to the invention are suitable for improving the lubricating properties of animal, vegetable, mineral or synthetic fuel oils with only low dosing rates. Due to their improved cold properties can be dispensed with storage and application to a warming and / or dilution. In addition, they simultaneously improve the refrigeration and Corrosion protection properties of the additized oils. The emulsifying properties of the additized oils are less affected than is the case with the lubricating additives of the prior art.
  • the additives of the invention are particularly well suited for use in middle distillates. As middle distillates are in particular those mineral oils which are obtained by distillation of crude oil and boil in the range of 120 to 450 ° C, for example kerosene, jet fuel, diesel and fuel oil.
  • the oils may also contain or consist of alcohols such as methanol and / or ethanol.
  • the additives of the invention are used in middle distillates containing 0.05% by weight of sulfur and less, more preferably less than 350 ppm of sulfur, more preferably less than 200 ppm of sulfur and in special cases less than 50 ppm of sulfur. These are generally those middle distillates that have been subjected to a hydrogenating refining, and therefore contain only small amounts of polyaromatic and polar compounds that give them a natural lubricating effect.
  • the additives according to the invention are furthermore preferably used in middle distillates which have 95% distillation points below 370.degree. C., in particular 350.degree. C. and in special cases below 330.degree. They can also be used as components in lubricating oils.
  • the mixtures can be used alone or together with other additives, e.g. with other pour point depressants or dewaxing aids, with corrosion inhibitors, antioxidants, sludge inhibitors, dehazers, conductivity improvers, lubricity additives, and cloud point depressant additives. Furthermore, they are successfully used in conjunction with additive packages, which i.a. known ashless dispersing additives, detergents, defoamers and corrosion inhibitors.
  • Table 1 Own point (pour point) of the additives of the invention Composition (parts by weight) Pour point example A1 A2 B1 B4 1 80 20 -9 2 50 50 -24 3 20 80 0 4 80 20 -9 5 50 50 -18 6 20 80 -15 7 80 20 -27 8th 50 50 -27 9 20 80 -6 10 80 20 -21 11 50 50 -21 12 20 80 -9 13 * 99.95 0.05 -36 14 * 99.95 0.05 -36 15 99.95 0.05 -15 V1 100 -9 V2 100 6 V3 100 9 V4 100 -6 V5 * 100 -36 * These examples are obtained with a 50% by weight adjustment of the fatty acid in solvent naphtha.
  • Composition (parts by weight) Cloud point example A1 A2 B1 B4 V6 * 100 -27.0 16. * 99.9995 0.0005 -33.0 17 * 99.9995 0.0005 -30.5 18 * 99,998 0,002 -33.5 19 * 99,998 0,002 -33.5 20 * 99.995 0.005 -31.0 21 * 99.995 0.005 -32.2 * These examples were obtained with a 50% by weight adjustment of the fatty acid in solvent naphtha.
  • MS is a mixture of a number of aliphatic and cyclic non-aromatic hydrocarbons.
  • the main components of MS can be found in the following table: Table 6: Components of MS component Concentration range (wt%) Di-2-ethylhexyl 10 - 25 2-ethylhexyl acid-2-ethylhexyl 10 - 25 C 16 lactones 4 - 20 2-Ethylhexylbutyrat 3 - 10 2-ethylhexanediol- (1,3) glycol mono-n-butyrate 5 - 15 2-ethylhexanol 4 - 10 C 4 to C 8 acetates 2 - 10 2-ethylhexanediol- (1,3) 2 - 5 Ethers and esters ⁇ C 20 0 - 20
  • the lubricating effect of the additives was carried out using an HFRR instrument from PCS Instruments on additized oils at 60 ° C.
  • the High Frequency Reciprocating Rig Test (HFRR) is described in D. Wei, H. Spikes, Wear, Vol. 111, No.2, p.217, 1986 , The results are given as coefficient of friction and Wear Scar (WS1.4). A low coefficient of friction and a low Wear Scar show a good lubricating effect.
  • test oils having the following characteristics were used: Test oil 1 Test oil 2 boiling range: 170 - 344 ° C 182-304 ° C density 0.830 g / cm 3 0.821 g / cm 3 Cloud point -9 ° C -33 ° C sulfur content 45 ppm 6 ppm

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Claims (16)

  1. Additifs stables au froid pour huiles combustibles d'une teneur en soufre allant jusqu'à 0,05 % en poids, contenant des mélanges d'acides gras composés de :
    A1) 1 à 99 % en poids d'au moins un acide mono- ou dicarboxylique saturé ayant de 6 à 50 atomes de carbone,
    A2) 1 à 99 % en poids d'au moins un acide mono- ou dicarboxylique insaturé ayant de 6 à 50 atomes de carbone,
    et
    B) au moins un composé azoté polaire, actif en tant que dispersant de paraffine dans les distillats moyens, présent dans une quantité allant de 0,01 à 90 % en poids par rapport au poids total des composants A1), A2) et B), qui comprend des terpolymères à base d'anhydrides d'acide dicarboxylique α,β-insaturés, de composés α,β-insaturés et d'éthers de polyoxyalkylène et d'alcools inférieurs insaturés, qui sont caractérisés en ce qu'ils contiennent
    de 20 à 80 % en mole de motifs structuraux bivalents des formules 12 et/ou 14, et éventuellement 13, les motifs structuraux 13 étant issus de radicaux anhydride n'ayant pas réagi,
    Figure imgb0049
    Figure imgb0050
    Figure imgb0051
     où
    R22 et R23 représentent, indépendamment l'un de l'autre, l'hydrogène ou un groupe méthyle,
    a, b valent zéro ou un et a + b vaut un,
    R24 et R25 sont identiques ou différents et représentent les groupes -NHR6, N (R6)2 et/ou -OR27, et R27 représente un cation de formule H2N(R6)2 ou H3NR6,
    Figure imgb0052
    de 19 à 80 % en mole de motifs structuraux bivalents de formule 15
    Figure imgb0053
     où
    R28 représente l'hydrogène ou un groupe alkyle en C1 à C4 et
    R29 un groupe alkyle en C6 à C60 ou aryle en C6 à C18, et
    de 1 à 30 % en mole de motifs structuraux bivalents de formule 16
    Figure imgb0054
     où
    R30 représente l'hydrogène ou un groupe méthyle,
    R31 l'hydrogène ou un groupe alkyle en C1 à C4,
    R33 un groupe alkylène en C1 à C4,
    m vaut de 1 à 100,
    R32 représente un groupe alkyle en C1 à C24, cycloalkyle en C5 à C20, aryle en C6 à C18 ou -C (O) -R34, et où
    R34 représente un groupe alkyle en C1 à C40, cycloalkyle en C5 à C10 ou aryle en C6 à C18.
  2. Additifs selon la revendication 1, dans lesquels le composant A comprend des acides carboxyliques ayant de 12 à 22 atomes de carbone.
  3. Additifs selon la revendication 1 et/ou 2, contenant de 1 à moins de 20 % en poids de composant A1) et plus de 80 à 99 % en poids de composant A2).
  4. Additifs selon une ou plusieurs des revendications 1 à 3, dans lesquels le mélange des composés A1) et A2) présente un indice d'iode d'au moins 40 g I/100 g.
  5. Additifs selon une ou plusieurs des revendications 1 à 4, dans lesquels le mélange des composés A1) et A2) comprend de 1 à 40 % en poids d'acides résiniques.
  6. Additifs selon une ou plusieurs des revendications 1 à 5, dans lesquels le composant B) contient de 40 à 60 % en mole de motifs structuraux bivalents des formules 12 et/ou 14, et éventuellement 13, de 39 à 60 % en mole de motifs structuraux bivalents de formule 15 et de 1 à 20 % en mole de motifs structuraux bivalents de formule 16.
  7. Additifs selon une ou plusieurs des revendications 1 à 6, dans lesquels les motifs structuraux des formules 12 à 14 sont dérivés de l'anhydride maléique, de l'anhydride itaconique ou de l'anhydride citraconique.
  8. Additifs selon une ou plusieurs des revendications 1 à 7, dans lesquels les motifs structuraux de formule 15 sont dérivés du styrène, de 1'α-méthylstyrène, du diméthylstyrène, de l'α-éthylstyrène, du diéthylstyrène, de l'i-propylstyrène, du tert.-butylstyrène, diisobutylène, décène, dodécène, tétradécène, pentadécène, hexadécène, octadécène, d'une α-oléfine en C20, d'une α-oléfine en C24, d'une α-oléfine en C30, du tripropényle, tétrapropényle, pentapropényle et de leurs mélanges.
  9. Additifs selon une ou plusieurs des revendications 1 à 8, dans lesquels les monomères de formule 20 sont produits par addition d'oxyde d'éthylène, d'oxyde de propylène et/ou d'oxyde de butylène sur l'alcool allylique, l'alcool méthallylique, le 3-butèn-1-ol, le 1-butèn-3-ol, le 2-méthyl-3-butèn-1-ol, le 2-méthyl-3-butèn-2-ol et le 3-méthyl-3-butèn-1-ol.
  10. Additifs selon une ou plusieurs des revendications 1 à 9, dans lesquels les amines utilisées dans la production des terpolymères sont choisies parmi la n-hexylamine, la n-octylamine, la n-tétradécylamine, la n-hexadécylamine, la n-stéarylamine, la N,N-diméthylaminopropylène diamine, la cyclohexylamine, la déhydroabiétylamine, la didécylamine, la ditétradécylamine, la distéarylamine, la diamine de coprah, la diamine de suif et leurs mélanges.
  11. Additifs selon une ou plusieurs des revendications 1 à 10, dans lesquels les terpolymères possèdent des valeurs K allant de 8 à 100 (mesurées selon Ubbelohde dans une solution à 5 % en poids de toluène à 25 °C).
  12. Solutions stables au froid d'additifs selon une ou plusieurs des revendications 1 à 11 dans des solvants organiques, les solutions contenant de 1 à 80 % en poids de solvant.
  13. Solutions stables au froid selon la revendication 12, dans lesquelles le solvant consiste en des hydrocarbures aliphatiques et/ou aromatiques et/ou oxygénés.
  14. Mélanges d'acides gras stables au froid composés de :
    A1) 1 à 99 % en poids d'au moins un acide mono- ou dicarboxylique saturé ayant de 6 à 50 atomes de carbone,
    A2) 1 à 99 % en poids d'au moins un acide mono- ou dicarboxylique insaturé ayant de 6 à 50 atomes de carbone,
    et
    B) au moins un composé azoté polaire, actif en tant que dispersant de paraffine dans les distillats moyens, présent dans une quantité allant de 0,01 à 90 % en poids par rapport au poids total des composants A1), A2) et B), qui comprend des terpolymères à base d'anhydrides d'acide dicarboxylique α,β-insaturés, de composés α,β-insaturés et d'éthers de polyoxyalkylène et d'alcools inférieurs insaturés, qui sont caractérisés en ce qu'ils contiennent
    de 20 à 80 % en mole de motifs structuraux bivalents des formules 12 et/ou 14, et éventuellement 13, les motifs structuraux 13 étant issus de radicaux anhydride n'ayant pas réagi,
    Figure imgb0055
    Figure imgb0056
    Figure imgb0057
     où
    R22 et R23 représentent, indépendamment l'un de l'autre, l'hydrogène ou un groupe méthyle,
    a, b valent zéro ou un et a + b vaut un,
    R24 et R25 sont identiques ou différents et représentent les groupes -NHR6, N(R6)2 et/ou -OR27 , et R27 représente un cation de formule H2N(R6)2 ou H3NR6,
    de 19 à 80 % en mole de motifs structuraux bivalents de formule 15
    Figure imgb0058
     où
    R28 représente l'hydrogène ou un groupe alkyle en C1 à C4 et
    R29 un groupe alkyle en C6 à C60 ou aryle en C6 à C18, et
    de 1 à 30 % en mole de motifs structuraux bivalents de formule 16
    Figure imgb0059
     où
    R30 représente l'hydrogène ou un groupe méthyle,
    R31 l'hydrogène ou un groupe alkyle en C1 à C4,
    R33 un groupe alkylène en C1 à C4,
    m vaut de 1 à 100,
    R32 représente un groupe alkyle en C1 à C24, cycloalkyle en C5 à C20, aryle en C6 à C18 ou -C (O) -R34, et où .
    R34 représente un groupe alkyle en C1 à C40, cycloalkyle en C5 à C10 ou aryle en C6 à C18.
  15. Huiles combustibles, contenant, outre un distillat moyen dont la teneur en soufre va jusqu'à 0,05 % en poids, un additif selon une ou plusieurs des revendications 1 à 14.
  16. Utilisation d'additifs selon une ou plusieurs des revendications 1 à 14 pour améliorer le pouvoir lubrifiant de distillats moyens pauvres en soufre, dont la teneur en soufre va jusqu'à 0,05 % en poids.
EP01126254A 2000-11-24 2001-11-06 Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant Expired - Lifetime EP1209215B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP07005870A EP1803791B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant
EP07005871A EP1801188B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant

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DE10058359A DE10058359B4 (de) 2000-11-24 2000-11-24 Brennstofföle mit verbesserter Schmierwirkung, enthaltend Mischungen aus Fettsäuren mit Paraffindispergatoren, sowie ein schmierverbesserndes Additiv
DE10058359 2000-11-24

Related Child Applications (2)

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EP07005871A Division EP1801188B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant
EP07005870A Division EP1803791B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant

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EP1209215A2 EP1209215A2 (fr) 2002-05-29
EP1209215A3 EP1209215A3 (fr) 2003-08-13
EP1209215B1 true EP1209215B1 (fr) 2007-10-10

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EP01126254A Expired - Lifetime EP1209215B1 (fr) 2000-11-24 2001-11-06 Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant
EP07005871A Expired - Lifetime EP1801188B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant
EP07005870A Revoked EP1803791B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant

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EP07005871A Expired - Lifetime EP1801188B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant
EP07005870A Revoked EP1803791B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant

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US (3) US6610111B2 (fr)
EP (3) EP1209215B1 (fr)
JP (1) JP5317380B2 (fr)
CA (1) CA2363700C (fr)
DE (4) DE10058359B4 (fr)
ES (1) ES2295098T3 (fr)

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Also Published As

Publication number Publication date
DE50114718D1 (de) 2009-04-02
USRE40758E1 (en) 2009-06-23
EP1209215A3 (fr) 2003-08-13
US6610111B2 (en) 2003-08-26
EP1801188A2 (fr) 2007-06-27
US20040083644A1 (en) 2004-05-06
DE10058359A1 (de) 2002-06-06
EP1803791B1 (fr) 2009-02-18
EP1801188B1 (fr) 2009-02-18
CA2363700A1 (fr) 2002-05-24
US20020095857A1 (en) 2002-07-25
JP2002167586A (ja) 2002-06-11
DE50114719D1 (de) 2009-04-02
DE10058359B4 (de) 2005-12-22
CA2363700C (fr) 2010-04-06
JP5317380B2 (ja) 2013-10-16
EP1803791A2 (fr) 2007-07-04
EP1803791A3 (fr) 2007-10-03
EP1209215A2 (fr) 2002-05-29
ES2295098T3 (es) 2008-04-16
DE50113115D1 (de) 2007-11-22
EP1801188A3 (fr) 2007-10-03

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