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  • 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 with improved low-temperature stability, and their use for Improvement of the lubricating effect of middle distillate fuel oils.
• Mineral oils and mineral oil distillates used as fuel oils generally contain 0.5 wt .-% and more sulfur, when burning causes the formation of sulfur dioxide. To the resulting To reduce environmental pollution, the sulfur content of fuel oils lowered further and further.
• the diesel fuel standard EN 590 writes in Germany currently has a maximum sulfur content of 350 ppm. In Scandinavia already comes in with fuel oils with less than 50 ppm Exceptional cases with less than 10 ppm sulfur for use.
• This Fuel oils are usually made by taking those from petroleum Fractions obtained by distillation hydrogenated refined. In the Desulphurization also removes other substances that Give fuel oils a natural lubricating effect. About these substances include polyaromatic and polar compounds.
• EP-A-0 798 364 discloses salts and amides from mono- to tetracarboxylic acids 2 to 50 carbon atoms and aliphatic mono- / polyamines with 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, e.g. Coconut fatty amine, tallow fatty amine and Oleylamine.
• WO-A-95/33805 discloses the use of cold flow improvers to improve the lubricating effect 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 carbon atoms and which can be in the form of a cation, are also mentioned as suitable substances.
• WO-A-96/18706 in analogy to WO-A-95/33805, discloses the use of those therein mentioned nitrogenous compounds in combination with lubricity additives.
• WO-A-96/23855 in analogy to WO-A-95/33805, discloses the use of those therein mentioned nitrogenous compounds in combination with detergent additives.
• the fatty acids used according to the prior art have the disadvantage that when stored at low temperatures, i.e. often at room temperature, mostly solidify at temperatures of 0 ° C at the latest at -5 ° C, or that separate crystalline components and cause handling problems. This Problem is also only partially due to dilution with organic solvents solve, since portions crystallize from these solutions or the solution gelled and froze. So they have to be strong for use as lubricity additives diluted, or held in heated storage containers and over heated Lines are dosed.
• the object underlying the present invention was to provide lubricity additives find that reduced the lubricating effect of middle distillates Improve dosing rates, but homogeneous, clear and in particular even in the cold remain fluid.
• Another object of the invention are cold stabilized solutions of Additives according to the invention in organic solvents, the solutions 1 to Contain 90 wt .-% solvent.
• Suitable solvents are aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures.
• the cold stabilized solutions according to the invention have an own pour point of below -40 ° C, preferably -45 ° C, especially -50 ° C.
• Another object of the invention is the use of the above Mixtures of components A and B to improve the Lubrication properties of low-sulfur middle distillates with up to 0.05% by weight Sulfur content.
• Preferred fatty acids are those with 8-40 carbon atoms, especially 12 - 22 carbon atoms.
• the alkyl residues of the fatty acids consist of essentially from carbon and hydrogen. However, you can choose more Substituents such as Hydroxy, halogen, amino or nitro groups, provided these do not affect the predominant hydrocarbon character.
• Component A2) can contain one or more double bonds and more natural or synthetic origin. With polyunsaturated carboxylic acids whose double bonds can be isolated or 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 means the combination of A1) and A2) contain at least 50% by weight, in particular at least 75% by weight, especially at least 90% by weight of the components one or more Double bonds.
• These preferred fatty acids (blends) have iodine numbers of at least 40 g I / 100 g, preferably at least 80 g I / 100 g, in particular at least 125 g I / 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, elaeosteric and Arachidonic acid, ricinoleic acid and those obtained from natural fats and oils Fatty acid mixtures, e.g. Coconut oil, peanut oil, fish, linseed oil, palm oil, Rapeseed oil, castor oil, castor oil, rapeseed oil, soybean oil, sunflower oil and tall oil fatty acid.
• Fatty acid mixtures e.g. Coconut oil, peanut oil, fish, linseed oil, palm oil, Rapeseed oil, castor oil, 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 as Paraffin dispersant in middle distillates effective polar nitrogenous compound.
• Paraffin dispersants reduce the size of those that precipitate in the cold Paraffin crystals and cause the paraffin particles not to settle, but to colloidal with significantly reduced sedimentation efforts, remain dispersed.
• Paraffin dispersants have become oil-soluble polar compounds with ionic or polar groups, e.g. Amine salts and / or amides proven by reaction aliphatic or aromatic amines, preferably long-chain aliphatic Amines, with aliphatic or aromatic mono-, di-, tri- or tetracarboxylic acids or their anhydrides are obtained.
• Paraffin dispersants also contain reaction products of secondary fatty amines 8 to 36 carbon atoms, especially dicocos fatty amine, ditallow fatty amine and Distearyl.
• Other paraffin dispersants are copolymers of Maleic anhydride and ⁇ , ⁇ -unsaturated compounds, optionally with primary monoalkylamines and / or aliphatic alcohols are implemented can, the reaction products of alkenylspirobislactones with amines and Reaction products of terpolymers based on ⁇ , ⁇ -unsaturated Dicarboxylic anhydrides, ⁇ , ⁇ -unsaturated compounds and polyoxyalkylene ethers lower unsaturated alcohols.
• Alkylphenol-formaldehyde resins are also available Paraffin dispersants suitable. The following are some suitable ones Paraffin dispersants listed.
• alkyl, cycloalkyl and aryl radicals can 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. The following may be mentioned in detail: 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 with 6 to 18 carbon atoms.
• the terpolymers consist of the bivalent structural units of the formulas 12 and 14 and 15 and 16 and possibly 13. They only contain in known in the polymerization by initiation, inhibition and chain termination end groups.
• Structural units of the formulas 12 to 14 are derived in particular 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.
• ⁇ , ⁇ -unsaturated olefins may be mentioned by way of example: styrene, ⁇ -methylstyrene, dimethylstyrene, ⁇ -ethylstyrene, diethylstyrene, i-propylstyrene, tert-butylstyrene, diisobutylene and ⁇ -olefins, such as decene, dodecene, tetradecene, pentadecene, Hexadecene, octadecene, C 20 - ⁇ -olefin, C 24 - ⁇ -olefin, C 30 - ⁇ -olefin, tripropenyl, tetrapropenyl, pentapropenyl and mixtures thereof.
• Alpha-olefins having 10 to 24 carbon atoms and styrene are preferred, alpha-olefin
• the structural units of the formula 16 are derived from polyoxyalkylene ethers of lower, unsaturated alcohols of the 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 -buten-2-ol and 3-methyl-3-buten-1-ol. Addition products of ethylene oxide and / or propylene oxide onto allyl alcohol are preferred.
• etherification products of the polyoxyalkylene ethers can also be prepared by adding ⁇ -olefin oxides, preferably ethylene oxide, propylene oxide and / or butylene oxide, to alcohols of the formula 22 R 32 - OH 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 and with polymerizable lower, unsaturated halides of the formula 23 implemented, where W stands for a halogen atom.
• the chlorides and bromides are preferably used as halides. Suitable production processes are mentioned, for example, in J. March, Advanced Organic Chemistry, 2nd edition, p.357f (1977).
• the esterification of the polyoxyalkylene ethers takes place by reaction with common esterification agents, such as carboxylic acids, carboxylic acid halides, carboxylic acid anhydrides or carboxylic acid esters with C 1 -C 4 alcohols.
• esterification agents such as carboxylic acids, carboxylic acid halides, carboxylic acid 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 aryl carboxylic acids are preferably used.
• the esterification is generally carried out at temperatures from 0 to 200 ° C., preferably 10 to 100 ° C.
• the index m indicates the degree of alkoxylation, i.e. the number of moles of ⁇ -olefin, the per mole of formula 20 or 21 be attached.
• Suitable primary amines suitable for the preparation of the terpolymers are the following: n-hexylamine, n-octylamine, n-tetradecylamine, n-hexadecylamine, n-stearylamine or also N, N-dimethylaminopropylenediamine, cyclohexylamine, dehydroabietylamine and mixtures thereof.
• Secondary amines which are suitable for the preparation of the terpolymers are for example: didecylamine, ditetradecylamine, distearylamine, Dicocos fatty amine, ditallow fatty amine and mixtures thereof.
• the terpolymers have K values (measured according to Ubbelohde in a 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 approximately 500 and 100,000. Suitable examples are listed in EP 606 055.
• the structural units of the formula 15 are derived from the ⁇ , ⁇ -unsaturated ones Olefins of the formula 19.
• the aforementioned alkyl, cycloalkyl and aryl radicals have the same meanings as under 8.
• radicals R 37 and R 38 in formula 25 and R 39 in formula 27 are derived from polyetheramines or alkanolamines of the formulas 28 a) and b), amines of the formula NR 6 R 7 R 8 and, if appropriate, from alcohols having 1 to 30 carbon atoms from.
• the preparation of the polyetheramines used is, for example, by reductive amination of polyglycols possible. Furthermore, it succeeds Production of polyetheramines with a primary amino group by Addition of polyglycols to acrylonitrile and subsequent catalytic Hydrogenation.
• polyetheramines are produced by the reaction of Polyethers with phosgene or thionyl chloride and subsequent amination accessible to polyetheramine.
• Polyetheramines are (e.g.) under the name ® Jeffamine (Texaco) commercially available. Their molecular weight is up to 2000 g / mol and the ethylene oxide / propylene oxide ratio is from 1:10 to 6: 1.
• Another way to derivatize the structural units of the Formulas 17 and 18 is that instead of the polyether amines Alkanolamine of the formulas 28a) or 28b) used and subsequently one Oxalkylation is subjected.
• 0.01 to 2 mol, preferably 0.01 to 1 mol, are used per mole of anhydride Alkanolamine used.
• the reaction temperature is between 50 and 100 ° C (amide formation). In the case of primary amines, the conversion takes place at temperatures above 100 ° C (imide formation).
• the oxyalkylation is usually carried out at temperatures between 70 and 170 ° C. with catalysis of bases, such as NaOH or NaOCH 3 , by gassing up alkylene oxides, such as ethylene oxide (EO) and / or propylene oxide (PO).
• bases such as NaOH or NaOCH 3
• alkylene oxides such as ethylene oxide (EO) and / or propylene oxide (PO).
• EO ethylene oxide
• PO propylene oxide
• 1 to 500, preferably 1 to 100, moles of alkylene oxide are added per mole of hydroxyl groups.
• alkanolamines Monoethanolamine, diethanolamine, N-methylethanolamine, 3-aminopropanol, Isopropanol, diglycolamine, 2-amino-2-methylpropanol and their mixtures.
• n-hexylamine n-octylamine, n-tetradecylamine, n-hexadecylamine, n-stearylamine or also N, N-dimethylaminopropylenediamine, cyclohexylamine, dehydroabietylamine and mixtures thereof.
• secondary amines examples include: Didecylamine, Ditetradecylamine, Distearylamine, Dicocosfettamin, Ditalgfettamin and their mixtures.
• alcohols examples include: Methanol, ethanol, propanol, isopropanol, n-, sec-, tert-butanol, octanol, tetradecanol, hexadecanol, octadecanol, tallow fatty alcohol, behenyl alcohol and mixtures thereof. Suitable examples are listed in EP-A-688 796.
• Preferred dicarboxylic acid is maleic acid or maleic anhydride.
• Copolymers of 10 to 90% by weight of C 6 -C 24 - ⁇ -olefins and 90 to 10% by weight of NC 6 -C 22 alkylmaleimide are preferred.
• the mixing ratio between A and B can vary within wide limits. So even small amounts B of 100 ppm to 50,000 ppm, preferably 1,000 ppm, are effective up to 10,000 ppm, in fatty acid solutions as a cold additive for A. They can do that Prevent self-crystallization of the fatty acid, which leads to a lowering of the Cloud Points leads, or to prevent the sedimentation of formed crystals and enable easy handling at reduced temperatures. For special solutions to problems can also range from 5% to 50%, in particular Cases up to 90% of ingredient B based on the amount of ingredient A. to be present. In particular, the additive's own pour point lowered and the lubricity of the additive oil improved. As a result, 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 oils in amounts of 0.001 to 0.5% by weight, preferably 0.001 to 0.1 wt .-% added. They can be as such or also dissolved in solvents such as aliphatic and / or aromatic Hydrocarbons or hydrocarbon mixtures such as e.g. 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 can be used.
• solvents such as aliphatic and / or aromatic Hydrocarbons or hydrocarbon mixtures such as e.g. Toluene, xylene, Ethylbenzene, decane, pentadecane, gasoline fractions, kerosene or commercial Solvent mixtures such as
• the additives even at low Temperatures of, for example, -40 ° C and lower are easily used can improve the lubricity of the additive oils and their Cold and corrosion protection properties.
• additives according to the invention also together with one or more oil-soluble Co-additives are used, which alone have the cold flow properties and / or improve the lubricating effect of crude oils, lubricating oils or fuel oils.
• oil-soluble Co-additives are copolymers containing vinyl acetate or Terpolymers of ethylene, comb polymers, alkylphenol-aldehyde resins and oil-soluble amphiphiles.
• the additives according to the invention in a mixture with ethylene / vinyl acetate / Vinyl neononanoic acid terpolymers or ethylene vinyl acetate / Vinyl neodecanoate terpolymers to improve the flowability of Mineral oils or mineral oil distillates.
• the terpolymers of Besides contain neononanoic acid vinyl ester or the neodecanoic acid vinyl ester Ethylene 10 to 35 wt .-% vinyl acetate and 1 to 25 wt .-% of the respective Neo compound.
• other preferred copolymers contain up to 35% by weight vinyl esters still 0.5 to 20% by weight olefin such as diisobutylene, 4-methylpentene or norbornene.
• the mixing ratio of the invention Additives with the ethylene / vinyl acetate copolymers described above or the terpolymers of ethylene, vinyl acetate and the vinyl esters of Neononanoic or neodecanoic acid is (in parts by weight) 20: 1 to 1:20, preferably 10: 1 to 1:10.
• alkylphenol-formaldehyde resins are those of the formula wherein R 50 is C 4 -C 50 alkyl or alkenyl, R 51 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.
• comb polymers This is understood to mean polymers in which hydrocarbon radicals having at least 8, in particular at least 10, carbon atoms are bonded to a polymer backbone. They are preferably homopolymers whose alkyl side chains contain at least 8 and in particular at least 10 carbon atoms. In copolymers, 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 an NC 6 -C 22 -alkylmaleimide (cf. EP 0 320 766) , also esterified olefin / maleic anhydride copolymers, polymers and copolymers of ⁇ -olefins and esterified copolymers of styrene and maleic anhydride.
• fumarate / vinyl acetate copolymers cf. EP 0 153 176 A1
• copolymers of a C 6 -C 24 - ⁇ -olefin and an NC 6 -C 22 -alkylmaleimide cf. EP 0 320 766
• esterified olefin / maleic anhydride copolymers polymers and copoly
• the additives according to the invention are suitable for the lubricating properties of animal, vegetable, mineral or synthetic fuel oils with only to improve low dosing rates. Due to their improved cold properties Can be heated and / or thinned during storage and use to be dispensed with. In addition, they improve the cold and Corrosion protection properties of the additive oils. The The emulsifying properties of the additive oils are less impaired than with the State-of-the-art lubricating additives are the case.
• the invention Additives are particularly well suited for use in middle distillates. As Middle distillates are referred to as those mineral oils that pass through Distillation of crude oil and boiling in the range of 120 to 450 ° C, for example kerosene, jet fuel, diesel and heating oil.
• the oils can also contain alcohols contain or consist of such as methanol and / or ethanol.
• the additives of the invention are used in such middle distillates that 0.05% by weight of sulfur and less, particularly preferably less than 350 ppm Sulfur, especially less than 200 ppm sulfur and in special cases contain less than 50 ppm sulfur. It is generally about those middle distillates which have been subjected to hydrogenating refining, and which therefore only contains small amounts of polyaromatic and polar compounds contain, which give them a natural lubricating effect.
• the Additives according to the invention are also preferably used in such Middle distillates used, the 95% distillation points below 370 ° C, in particular 350 ° C and in special cases below 330 ° C. You can also use it as a Components are used in lubricating oils.
• the mixtures can be used alone or together with other additives be used, e.g. with other pour point depressors or Dewaxing aids, with corrosion inhibitors, antioxidants, Sludge inhibitors, dehazers, conductivity improvers, lubricity additives, and Additions to lower the cloud point. Furthermore, they become successful used together with additive packages that include known ashless Contain dispersing additives, detergents, defoamers and corrosion inhibitors.
• 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 (% by weight) 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 device from PCS Instruments on additive 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 the 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 with the following characteristics were used to test the lubricating effect: 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
• the boiling data are determined in accordance with ASTM D-86 and the cloud point in accordance with ISO 3015.
• Wear Scar in Test Oil 1 example additive Wear scar Friction V15 Without 555 ⁇ m 0.33 63 100 ppm according to Ex. 37 385 ⁇ m 0.18 64 100 ppm A1 + 150 ppm B4 381 ⁇ m 0.18 V16 100 ppm A1 421 ⁇ m 0.18 V17 150 ppm B4 549 ⁇ m 0.34 Wear Scar in Test Oil 2 example additive Wear scar Friction V18 without 637 ⁇ m 0.30 65 200 ppm according to Ex. 42 386 0.18 66 200 ppm according to Ex. 48 395 0.18 V19 200 ppm according to example V13 405 0.19

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