Classifications

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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
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  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
  • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
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  • C10L1/00—Liquid carbonaceous fuels
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  • 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
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  • C10L1/00—Liquid carbonaceous fuels
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  • 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
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1981—Condensation polymers of aldehydes or ketones
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1983—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyesters
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  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
  • C10L1/1986—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters complex polyesters
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  • 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
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  • C10L1/00—Liquid carbonaceous fuels
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  • 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
  • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/22—Organic compounds containing nitrogen
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  • C10L1/224—Amides; Imides carboxylic acid amides, imides
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  • C10L1/00—Liquid carbonaceous fuels
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  • 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

Definitions

• the invention relates to low sulfur mineral oil distillates having improved cold flowability and paraffin dispersion comprising an ester of an alkoxylated polyol and a copolymer of ethylene and unsaturated esters, paraffin dispersing additives and their use.
• crude oils and middle distillates obtained by distillation of crude oils such as gas oil, diesel oil or fuel oil
• crude oils and middle distillates obtained by distillation of crude oils contain different amounts of n-paraffins which crystallize out as platelet-shaped crystals when the temperature is lowered and partly agglomerate with the inclusion of oil.
• the flow properties of the oils or distillates deteriorate, which can lead to disruptions in the extraction, transport, storage and / or use of the mineral oils and mineral oil distillates.
• the crystallization phenomenon especially in winter, can lead to deposits on the pipe walls, in individual cases, for example when a pipeline is at a standstill, even to its complete blockage.
• mineral oils In storage and Further processing of the mineral oils may also be required in winter to store the mineral oils in heated tanks.
• blockages of the filters in diesel engines and firing systems may occur, as a result of which reliable metering of the fuels is prevented and, under certain circumstances, a complete interruption of the fuel or heating agent supply occurs.
• Typical flow improvers for crude oils and middle distillates are copolymers and terpolymers of ethylene with carboxylic acid esters of vinyl alcohol.
• Another object of flow improver additives is the dispersion of paraffin crystals, i. the delay or prevention of the sedimentation of paraffin crystals and thus the formation of a paraffin-rich layer at the bottom of storage containers.
• EP-A-0 061 895 discloses cold flow improvers for mineral oil distillates which Contain esters, ethers or mixtures thereof.
• the esters / ethers contain two linear saturated C 10 to C 30 alkyl groups and one polyoxyalkylene group at 200 to 5000 g / mol.
• EP 0 973 848 and EP 0 973 850 disclose mixtures of esters of alkoxylated alcohols having more than 10 carbon atoms and fatty acids having 10 to 40 carbon atoms in combination with ethylene copolymers as flow improvers.
• EP-A-0 935 645 discloses alkylphenol-aldehyde resins as an oil-improving additive in low-sulfur middle distillates.
• EP-A-0857776 and EP 1088045 disclose processes for improving the flowability of paraffin-containing mineral oils and mineral oil distillates by adding ethylene copolymers and alkylphenol-aldehyde resins and optionally further, nitrogen-containing paraffin dispersants.
• US-A-3,762,888 discloses additive blends containing, in addition to oil-soluble, polymeric cold flow improvers, another oil-soluble nitrogen-free and flow-improving additive component and improving the cold flow properties of middle distillates.
• an additive which, in addition to copolymers of ethylene and unsaturated esters, also contains fatty acid esters of certain alkoxylated polyols, represents a particularly good cold flow improver.
• the invention thus middle distillates with a maximum of 0.05 wt .-% sulfur content, the fatty acid esters of alkoxylated polyols (A) having an OH number of at most 15 mg KOH / g and at least one Kaltf occidentalverlutterer (B), said Kaltf occidentalverlutterer at least one Copolymer of ethylene and one or more ethylenically unsaturated carboxylic acid esters having an ethylene content of 60 to 90 mol%, and the polyols contain at least 3 OH groups.
• Another object of the invention is the use of an additive comprising at least one fatty acid ester of alkoxylated polyols (A) having an OH number of at most 15 mg KOH / g and at least one cold flow improver (B), said cold flow improver at least one copolymer of ethylene and a or more ethylenically unsaturated carboxylic acid esters having an ethylene content of 60 to 90 mol%, and the polyols contain at least 3 OH groups to improve the cold flow properties and paraffin dispersion of middle distillates with a maximum of 0.05 wt .-% sulfur content.
• A fatty acid ester of alkoxylated polyols
• B cold flow improver
• the polyols contain at least 3 OH groups to improve the cold flow properties and paraffin dispersion of middle distillates with a maximum of 0.05 wt .-% sulfur content.
• Another object of the invention is a method for improving the cold flow properties of middle distillates with a maximum of 0.05 wt .-% sulfur content by the middle distillates an additive containing at least one fatty acid ester of alkoxylated polyols (A) having an OH number of at most 15 mg KOH / g and at least one cold flow improver (B), said cold flow improver comprising at least one copolymer of ethylene and one or more ethylenically unsaturated carboxylic acid esters having an ethylene content of 60 to 90 mole%, and said polyols containing at least 3 OH groups.
• A fatty acid ester of alkoxylated polyols
• B cold flow improver comprising at least one copolymer of ethylene and one or more ethylenically unsaturated carboxylic acid esters having an ethylene content of 60 to 90 mole%, and said polyols containing at least 3 OH groups.
• the esters (A) are derived from polyols having 3 or more OH groups, in particular glycerol, trimethylolpropane, pentaerythritol and the oligomers having 2 to 10 monomer units, such as polyglycerol, obtainable therefrom by condensation.
• the polyols are generally containing from 1 to 100 mol of alkylene oxide, preferably 3 to 70, in particular 5 to 50 mol of alkylene oxide reacted per mole of polyol.
• Preferred alkylene oxides are ethylene oxide, propylene oxide and butylene oxide.
• the alkoxylation is carried out by known methods.
• the fatty acids suitable for the esterification of the alkoxylated polyols preferably have 8 to 50, in particular 12 to 30, especially 16 to 26 C-atoms.
• Suitable fatty acids are, for example, lauric, tridecane, myristic, pentadecane, palmitic, margarine, stearic, isostearic, arachic and behenic, oleic and erucic acid, palmitoleic, myristolein, ricinoleic acid, as well as natural fats and Oils derived fatty acid mixtures.
• Preferred fatty acid mixtures contain more than 50% fatty acids with at least 20 C atoms.
• fatty acids used for esterification contain double bonds, in particular less than 10%; specifically, they are largely saturated. Under largely saturated here is an iodine value of the fatty acid used of up to 5 g l per 100 g fatty acid are understood.
• Esterification may also be carried out starting from reactive derivatives of the fatty acids such as esters with lower alcohols (e.g., methyl or ethyl esters) or anhydrides.
• polybasic carboxylic acids dimer fatty acids, alkenylsuccinic acids and aromatic polycarboxylic acids and derivatives thereof such as anhydrides and C 1 - to C 5 -esters.
• Alkenylsuccinic acid and its derivatives with alkyl radicals having 8 to 200, in particular 10 to 50, C atoms are preferred.
• Examples are dodecenyl, octadecenyl and poly (isobutenyl) succinic anhydride.
• the polybasic carboxylic acids are preferably used to lower levels of up to 30 mol%, preferably 1 to 20 mol%, in particular 2 to 10 mol%.
• Ester and fatty acid are used for the esterification based on the content of hydroxyl groups on the one hand and carboxyl groups on the other hand in the ratio of 1.5: 1 to 1: 1.5, preferably 1.1: 1 to 1: 1.1, in particular equimolar.
• the paraffin-dispersing action is particularly pronounced when working with an excess of acid of up to 20 mol%, especially up to 10 mol%, in particular up to 5 mol%.
• the esterification is carried out by conventional methods. Has proven particularly useful the implementation of Polyolalkoxilat with fatty acid, optionally in the presence of catalysts such as para-toluenesulfonic acid, C 2 - to C 50- alkylbenzene sulfonic acids, methanesulfonic acid or acidic ion exchangers.
• catalysts such as para-toluenesulfonic acid, C 2 - to C 50- alkylbenzene sulfonic acids, methanesulfonic acid or acidic ion exchangers.
• the separation of the water of reaction can be carried out by distillation by direct condensation or preferably by azeotropic distillation in the presence of organic solvents, in particular aromatic solvents such as toluene, xylene or higher boiling mixtures such as ® Shellsol A, Shellsol B, Shellsol AB or Solvent Naphtha.
• the esterification is preferably carried out completely, ie for the esterification 1.0 to 1.5 moles of fatty acid are used per mole of hydroxyl groups.
• the acid number of the esters is below 15 mg KOH / g, preferably below 10 mg KOH / g especially below 5 mg KOH / g.
• Copolymer (B) is preferably an ethylene copolymer having an ethylene content of 60 to 90 mol% and a comonomer content of 10 to 40 mol%, preferably 12 to 18 mol%.
• Copolymer (B) is more preferably a main chain polymer which is not a graft copolymer.
• Suitable comonomers are vinyl esters of aliphatic carboxylic acids having 2 to 15 carbon atoms.
• Preferred vinyl esters for copolymer B) are vinyl acetate, vinyl propionate, vinyl hexanoate, vinyl octanoate, vinyl 2-ethylhexanoate, vinyl laurate and vinyl esters of neocarboxylic acids, here in particular neononan, neodecane and neoundecanoic acid.
• an ethylene-vinyl acetate copolymer an ethylene-vinyl propionate copolymer, an ethylene-vinyl acetate-vinyl octanoate terpolymer, an ethylene-vinyl acetate-vinyl-2-ethylhexanoate terpolymer, an ethylene-vinyl acetate-neononanoic acid vinyl ester terpolymer, or an ethylene -Vinylacetat-neodecanoate terpolymer.
• Preferred acrylic acid esters are acrylic esters having alcohol radicals of from 1 to 20, in particular from 2 to 12 and especially from 4 to 8 carbon atoms, such as, for example, methyl acrylate, ethyl acrylate and 2-ethylhexyl acrylate.
• the Copolymers may contain up to 5% by weight of other comonomers.
• Such comonomers may be, for example, vinyl esters, vinyl ethers, alkyl acrylates, alkyl methacrylates having C 1 to C 20 alkyl radicals, isobutylene and olefins.
• Preferred as higher olefins are hexene, isobutylene, octene and / or diisobutylene.
• Suitable comonomers are olefins such as propene, hexene, butene, isobutene, diisobutylene, 4-methylpentene-1 and norbornene. Particularly preferred are ethylene-vinyl acetate-diisobutylene and ethylene-vinyl acetate-4-methylpentene-1 terpolymers.
• the copolymers have melt viscosities at 140 ° C of 20 to 10,000 mPas, especially from 30 to 5000 mPas, especially from 50 to 2000 mPas.
• the copolymers (B) can be prepared by the usual copolymerization methods such as suspension polymerization, solvent polymerization, gas phase polymerization or high-pressure bulk polymerization. Preference is given to the high-pressure mass polymerization at pressures of preferably 50 to 400, in particular 100 to 300 MPa and temperatures of preferably 50 to 350, in particular 100 to 250 ° C.
• the reaction of the monomers is initiated by free radical initiators (free radical initiators).
• 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 permalate, 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 individually or as a mixture of two or more substances in amounts of 0.01 to 20 wt .-%, preferably 0.05 to 10 wt .-%, based on the monomer mixture.
• the high-pressure mass polymerization is carried out batchwise or continuously in known high-pressure reactors, for example autoclaves or tubular reactors, 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.
• the solvent-free mode of operation is preferred.
• the monomer streams may be composed differently (EP-A-0 271 738).
• alkylphenol-aldehyde resins (C), paraffin dispersants (D) and / or comb polymers can also be added to the fuel oils according to the invention which contain components (A) and (B). Accordingly, preferred embodiments are also the use according to the invention of additives which additionally contain alkylphenol-aldehyde resins (C), paraffin dispersants (D) and / or comb polymers, and the corresponding process.
• Alkylphenol-aldehyde resins (C) are known in principle and, for example, in Römpp Chemie Lexikon, 9th edition, Thieme Verlag 1988-92, Volume 4, p 3351ff. described.
• the alkyl radicals of the o- or p-alkylphenol have 1 to 50, preferably 4 to 20, in particular 6 to 12, carbon atoms; it is preferably 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 as well as tetrapropenyl, pentapropenyl and polyisobutenyl.
• the alkylphenol-aldehyde resin may also contain up to 50 mole% phenol units.
• the same or different alkylphenols may be used.
• the aliphatic aldehyde in the alkylphenol-aldehyde resin has 1 to 10, preferably 1 to 4, carbon atoms and may carry other functional groups such as aldehyde or carboxyl groups. It is preferably formaldehyde.
• the molecular weight of the alkylphenol-aldehyde resins is 400-10,000, preferably 400-5,000, g / mol. The prerequisite here is that the resins are oil-soluble.
• the preparation of the alkylphenol-aldehyde resins is carried out in a known manner by basic catalysis, resulting in condensation products of the resol type, or by acid catalysis to produce novolac-type condensation products.
• the condensates obtained according to both types are suitable for the compositions according to the invention.
• the condensation is in the presence of acidic catalysts.
• alkylphenol-aldehyde resins are a bifunctional o- or p-alkylphenol having 1 to 50 carbon atoms, preferably 4 to 20, in particular 6 to 12 carbon atoms per alkyl group, or mixtures thereof and an aliphatic aldehyde with 1 to 10 C atoms reacted with each other, wherein per mole of alkylphenol about 0.5 to 2 mol, preferably 0.7 to 1.3 mol and in particular equimolar amounts of aldehyde are used.
• Suitable alkylphenols are, in particular, C 4 -C 50 -alkylphenols, for example o- or p-cresol, n-, sec- and tert-butylphenol, n- and i-pentylphenol, n- and isohexylphenol, n- and - iso-octylphenol, n- and iso-nonylphenol, n- and iso-decylphenol, n- and iso-dodecylphenol, tetradecylphenol, hexadecylphenol, octadecylphenol, eicosylphenol, tripropenylphenol, tetrapropenylphenol and polyis (isobutenyl) phenol.
• C 4 -C 50 -alkylphenols for example o- or p-cresol, n-, sec- and tert-butylphenol, n- and i-p
• the alkylphenols are preferably para-substituted. They are preferably substituted at most 7 mol%, in particular at most 3 mol% with more than one alkyl group.
• aldehydes are formaldehyde, acetaldehyde, butyraldehyde and glutaraldehyde, with formaldehyde being preferred.
• the formaldehyde can be used in the form of paraformaldehyde or in the form of a preferably 20 to 40% strength by weight aqueous formalin solution. Corresponding amounts of trioxane can also be used.
• alkylphenol and aldehyde is usually carried out in the presence of alkaline catalysts, for example alkali metal hydroxides or alkylamines, or of acidic catalysts, for example inorganic or organic Acids such as hydrochloric acid, sulfuric acid, phosphoric acid, sulfonic acid, sulfamido acids or haloacetic acids, and in the presence of an azeotrope with water forming organic solvent, for example toluene, xylene, higher aromatics or mixtures thereof.
• the reaction mixture is heated to a temperature of 90 to 200 ° C, preferably 100 to 160 ° C, wherein the resulting reaction water is removed during the reaction by azeotropic distillation.
• Solvents that do not release protons under condensation conditions may remain in the products after the condensation reaction.
• the resins can be used directly or after neutralization of the catalyst, optionally after further dilution of the solution with aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures, eg gasoline fractions, kerosene, decane, pentadecane, toluene, xylene, ethylbenzene or solvents such as ® Solvent Naphtha, ® Shellsol AB, ® Solvesso 150, ® Solvesso 200, ® Exxsol, ® ISOPAR and ® Shellsol D types.
• the alkylphenol resins can then optionally be alkoxylated by reaction with 1 to 10, especially 1 to 5 moles of alkylene oxide such as ethylene oxide, propylene oxide or butylene oxide per phenolic OH group.
• the polar nitrogen-containing paraffin dispersants (D) are low molecular weight or polymeric, oil-soluble nitrogen compounds, for example amine salts, imides and / or amides, which are 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.
• Particularly preferred paraffin dispersants contain reaction products of secondary fatty amines having 8 to 36 carbon atoms, in particular dicoco fatty amine, ditallow fatty amine and distearylamine.
• Other paraffin dispersants are copolymers of maleic anhydride and .alpha.,.
• Beta.-unsaturated compounds which can optionally be reacted with primary monoalkylamines and / or aliphatic alcohols, the reaction products of alkenylspirobislactones with amines and reaction products of ⁇ , ⁇ -unsaturated terpolymers Dicarboxylic acid anhydrides, ⁇ , ⁇ -unsaturated compounds and polyoxyalkylene ethers of lower unsaturated alcohols.
• D paraffin dispersants
• 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 having 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 1 and 3 and 4 and 5 and optionally 2. 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 1 to 3 are derived from ⁇ , ⁇ -unsaturated dicarboxylic acid anhydrides of the formulas 6 and 7 such as maleic anhydride, itaconic anhydride, citraconic anhydride, preferably maleic anhydride.
• the structural units of the formula 4 are derived from the ⁇ , ⁇ -unsaturated compounds of the formula 8.
• ⁇ -unsaturated olefins examples which may be mentioned are the following ⁇ , ⁇ -unsaturated olefins: 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.
• ⁇ -olefins having 10 to 24 C atoms and
• the structural units of the formula 5 are derived from polyoxyalkylene ethers of lower, unsaturated alcohols of the formula 9.
• ⁇ -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 butene-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 II R 32 - OH (11) wherein R 32 is C 1 -C 24 -alkyl, C 5 -C 20 -cycloalkyl or C 6 -C 18 -aryl, deposited by known methods and with polymerizable lower, unsaturated halides of the formula 12th 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 preferably 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 primary amines for the preparation of the terpolymers are the following: n-hexylamine, n-octylamine, n-tetradecylamine, n-hexadecylamine, n-stearylamine or else N, N-dimethylaminopropylenediamine, cyclohexylamine, dehydroabietylamine and mixtures thereof.
• 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 listed in EP 606,055.
• the structural units of the formulas 13, 14 and 15 are derived from ⁇ , ⁇ -unsaturated dicarboxylic acid anhydrides of the formulas 6 and / or 7.
• the structural units of the formula 4 are derived from the ⁇ , ⁇ -unsaturated Olefins of the formula 8 from.
• the abovementioned alkyl, cycloalkyl and aryl radicals have the same meanings as under 8.
• radicals R 37 and R 38 in formula 13 or R 39 in formula 15 are derived from polyetheramines or alkanolamines of the formulas 16 a) and b), amines of the formula NR 6 R 7 R 8 and optionally of alcohols having 1 to 30 carbon atoms from.
• polyetheramines used are possible, for example, by reductive amination of polyglycols. Furthermore, it is possible to prepare polyetheramines having a primary amino group by addition of polyglycols to acrylonitrile and subsequent catalytic hydrogenation. In addition, polyetheramines are accessible by reaction of polyethers with phosgene or thionyl chloride and subsequent amination to the polyetheramine.
• the polyetheramines used according to the invention are commercially available (for example) under the name Jeffamine (Texaco). Its molecular weight is up to 2000 g / mol and the ethylene oxide / propylene oxide ratio is from 1:10 to 6: 1.
• a further possibility for derivatizing the structural units of the formulas 6 and 7 is that, instead of the polyether amines, an alkanolamine of the formula 16a) or 16b) is used and subsequently subjected to alkoxylation.
• reaction temperature is between 50 and 100 ° C (amide formation). In the case of primary amines, the reaction takes place at temperatures above 100 ° C (imide formation).
• the alkoxylation is usually carried out at temperatures between 70 and 170 ° C with catalysis of bases, such as NaOH or NaOCH 3 , by gassing of 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 include: Monoethanolamine, diethanolamine, N-methylethanolamine, 3-aminopropanol, isopropanol, diglycolamine, 2-amino-2-methylpropanol and theirs Mixtures.
• n-hexylamine for example, the following may be mentioned: n-hexylamine, n-octylamine, n-tetradecylamine, n-hexadecylamine, n-stearylamine or else N, N-dimethylaminopropylenediamine, cyclohexylamine, dehydroabietylamine and mixtures thereof.
• secondary amines examples include: Didecylamine, ditetradecylamine, distearylamine, dicocosfettamine, ditallow fatty amine and mixtures thereof.
• alcohols which may be mentioned are: 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 (in parts by weight) of the additives according to the invention with paraffin dispersants, resins or comb polymers is in each case 1:10 to 20: 1, preferably 1: 1 to 10: 1.
• the additive components according to the invention can be separated or mixed in mineral oils or mineral oil distillates.
• the individual additive constituents or else the corresponding mixture are dissolved or dispersed in an organic solvent or dispersion medium before addition to the middle distillates.
• the solution or dispersion generally contains 5-90, preferably 5-75 wt .-% of the additive or additive mixture.
• Suitable solvents or dispersants are aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures, for example gasoline fractions, kerosene, decane, Pentadecane, toluene, xylene, ethylbenzene or commercial solvent mixtures such as Solvent Naphtha, Shellsol AB, Solvesso 150, Solvesso 200, Exxsol, ISOPAR and Shellsol D grades.
• polar solubilizers such as 2-ethylhexanol, decanol, iso-decanol or iso-tridecanol can be added.
• Mineral oils or mineral oil distillates improved in their refrigeration properties by the additives according to the invention contain from 0.001 to 2, preferably from 0.005 to 0.5,% by weight of the additives, based on the mineral oil or mineral oil distillate.
• the additives according to the invention are particularly suitable for improving the cold flow properties of animal, vegetable or mineral oils. At the same time they improve the dispersion of the precipitated paraffins below the cloud point. They are particularly well suited for use in middle distillates.
• 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 additives of the present invention are used in low sulfur middle distillates containing 350 ppm sulfur and less, more preferably less than 200 ppm sulfur, and more preferably less than 50 ppm sulfur.
• the additives according to the invention are furthermore preferably used in middle distillates which have 95% distillation points below 365 ° C., in particular 350 ° C. and in special cases below 330 ° C., and in addition to high contents of paraffins having 18 to 24 C atoms only small proportions Containing paraffins with chain lengths of 24 and more carbon atoms. They can also be used as components in lubricating oils.
• the mineral oils or mineral oil distillates may also contain other conventional additives such as dewaxing aids, corrosion inhibitors, antioxidants, lubricity additives, sludge inhibitors, cetane number improvers, detergent additives, dehazers, Contains conductivity improvers or dyes.
• esters A were used as a 50% solution in aromatic solvent (EO stands for ethylene oxide, PO stands for propylene oxide): Table 1: Characterization of the esters used (constituent A) Main components of fatty acids acid number OH number additive polyol alkoxylation C 18 C 20 C 22 [mg KOH / g] [mg KOH / g] A1 glycerin 22 mol EO 2 7 88 7 13 A2 glycerin 22 mol EO 95% 5 4 A3 glycerin 22 mol EO 37 10 48 1 2 A4 glycerin 16 mol PO 37 10 48 7 9 A5 glycerin 16 mol PO 2 7 88 5 7 A6 glycerin 24 mol PO 37 10 48 8th 11 A7 glycerin 10 mol EO 2 7 88 7 9 A8 glycerin 30 mol EO 2 7 88 2 4 A9 glycerin 40 mol EO 2 7 88 12 10 A10 g
• the viscosity is determined according to ISO 3219 / B using a rotary viscometer (Haake RV20) with a plate-and-cone measuring system at 140 ° C.
• the additives are used to improve the handling as 50% solutions in solvent naphtha or kerosene.
• the boiling characteristics are determined according to ASTM D-86, the CFPP value according to EN 116 and the determination of the cloud point according to ISO 3015.
• Table 2 Characteristics of the test oils Test oil 1 Test oil 2 Test oil 3 Test oil 4 Start of boiling [° C] 169 200 174 241 20% [° C] 211 251 209 256 90% [° C] 327 342 327 321 95% [° C] 344 354 345 341 Cloud Point [° C] -9.0 -4.2 -6.7 -8.2 CFPP [° C] -10 -6 -8th -10 sulfur content 33 ppm 35 ppm 210 ppm 45 ppm
• Table 4 describes the superior efficiency of the inventive additives in comparison with the prior art together with ethylene copolymers for mineral oils and mineral oil distillates by means of the CFPP test (Cold Filter Plugging Test according to EN 116).
• the paraffin dispersion in middle distillates was determined in the short sediment test as follows: 150 ml of the middle distillates added with the additive components indicated in the table were cooled to -13 ° C. in a cold cabinet at -2 ° C./hour in 200 ml graduated cylinders and stored at this temperature for 16 hours. Subsequently, the volume and appearance of both the sedimented paraffin phase and the overlying oil phase were determined and assessed visually.
• a small amount of sediment with simultaneously homogeneously turbid oil phase or a large sediment volume with a clear oil phase show a good paraffin dispersion.
• the lower 20% by volume were isolated and the cloud point was determined according to ISO 3015. Only a small deviation of the cloud point of the lower phase (CP KS ) from the blank value of the oil shows a good paraffin dispersion.
• Table 3 CFPP activity in test oil 1
• the CFPP activity of the esters A according to the invention was measured in combination with equal amounts of C and D in test oil 1 as follows: A C D B3 in ppm 50 75 100 example 1 50 ppm A1 50 ppm C1 50 ppm D2 -29 -31 -30
• Example 2 50 ppm A11 50 ppm C2 50 ppm D1 -27 -30 -30
• Example 3 50 ppm A7 50 ppm C1 50 ppm D2 -17 -28 -29
• Example 4 50 ppm A12 50 ppm C1 50 ppm D2 -19 -31 -29
• Example 5 50 ppm A8 50 ppm C1 50 ppm D2 -21 -29 -29
• Example 6 50 ppm A9 50 ppm C1 50 ppm D2 -18 -24 -29
• Example 7 50 ppm A2 50 ppm C1 50 ppm D2
• Test oil 3 (CP -6.7 ° C) A C Sediment [vol.%] Appearance oil phase CFPP [° C] CP KS [° C]
• Example 21 100 ppm A1 50 ppm C1 0 cloudy -23 -5.9
• Example 22 100 ppm A1 50 ppm C2 7 cloudy -24 -3.3
• Example 23 100 ppm A2 50 ppm C2 10 cloudy -21 -2.4
• Example 24 100 ppm A1 50 ppm C3 20 cloudy -21 -0.8
• Example 25 50 ppm A2 100 ppm C1 20 cloudy -26 -ä1,4
• Example 26 100 ppm A3 50 ppm C1 10 cloudy -28 -1.4
• Example 27 50 ppm A3 100 ppm C1 0 cloudy -28 -5.3
• Example 28 100 ppm A4 100 ppm C1 7 cloudy -21 -3.6
• Example 29 50 ppm A4
• Test oil 4 (CP -8,2 ° C) A C Sediment [vol.%] Appearance oil phase CFPP [° C] CP KS [° C]
• Example 40 100 ppm A1 100 ppm C1 0 cloudy -24 -6.3
• Example 41 100 ppm A1 100 ppm C1 0 cloudy -24 -7.5
• Example 42 50 ppm A3 100 ppm C1 0 cloudy -24 -5.4
• Example 43 50 ppm A3 100 ppm C1 0 cloudy -28 -5.3
• Example 44 100 ppm A5 50 ppm C1 50 cloudy -23 -3.3
• Example 45 100 ppm A5 100 ppm C1 0 cloudy -23 -5.5
• Example 46 50 ppm A5 100 ppm C1 70 cloudy -24 -4.3
• Example 47 100 ppm A14 50 ppm C1 16 clear -18 -1.1
• Example 48 150 ppm A1

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