Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
  • C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-carboxylic
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
  • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups

Definitions

• the present invention relates to petroleum middle distillates which contain small amounts of a conventional flow improver based on ethylene and copolymers of ethylenically unsaturated carboxylic acid esters of long-chain n-alkanols with long-chain alkyl vinyl ethers and ethylenically unsaturated dicarboxylic acid derivatives which are characterized by improved flow properties in the cold.
• Middle distillates such as gas oils, diesel oils or heating oils, which are obtained from petroleum by distillation, have different levels of paraffins depending on the origin of the crude oil and depending on the processing method in the refinery.
• the proportion of long-chain n-paraffins in particular determines the cold flow behavior of such distillates.
• the n-paraffins Upon cooling, the n-paraffins separate out as platelet-shaped, interlocking crystals that build up a three-dimensional network (house of cards structure), in which large quantities of still liquid distillate are enclosed and immobilized.
• the crystallization of the n-paraffins is accompanied by a decrease in fluidity and an increase in viscosity. This makes it difficult to supply middle distillates to the combustion units, the failed paraffins clog upstream filters, so that in extreme cases the supply can completely stop.
• ethylene copolymers especially copolymers of ethylene and unsaturated esters, such as those e.g. are described in DE-A-21 02 469 or EP-A-84 148.
• DE-A-25 31 234 recommends the addition of alternating copolymers containing maleic acid diamide or maleimide structures as stabilizers in mineral oils, i.e. the carboxyl groups are completely reacted with amines to give the diamides or imides.
• reaction products of monoamines with maleic anhydride polymers to the corresponding imides are also described, wherein when using less than one mole of amine per mole of maleic anhydride unit, remaining carboxyl groups are converted into metal salts by neutralization.
• alkyl vinyl ether and monovinyl hydrocarbons are preferably used.
• FR-A-2 592 658 describes mixtures of an ethylene polymer and a reaction product of a primary amine with a copolymer of, for example, alkyl acrylates and / or alkyl vinyl ethers, diisobutene and maleic anhydride and their use as an additive to middle distillates.
• EP-A-360 419 describes middle distillates which contain polymers of vinyl ethers with hydrocarbon radicals of 1 to 17 carbon atoms.
• the following are among the comonomers: Called alkyl acrylates or methacrylates. In the examples, however, only polymers from alkyl vinyl ethers with up to 4 carbon atoms in the side chain are described.
• These C1 to C4 vinyl ethers are copolymerized with maleic or fumaric acid derivatives. Examples of copolymers with acrylic acid derivatives are not given.
• the claimed additives can be used together with other flow improvers.
• EP-A-283 293 discloses the use of polymers with at least one amide group from a secondary amine and a carboxyl group as an additive to middle distillates.
• the polymers can include by copolymerization of unsaturated esters with maleic anhydride and subsequent reaction with the secondary amine.
• the unsaturated ester monomers include Dialkyl fumarates and vinyl acetate are described.
• the copolymers B consist of 10 to 90 mol%, preferably 40 to 90 mol% and particularly preferably 60 to 90 mol% of alkyl (meth) acrylates, 5 to 60 mol%, preferably 5 to 40 mol -% and especially preferably 10 to 30 mol% of olefinically unsaturated dicarboxylic acids or their anhydrides, 5 to 60 mol%, preferably 5 to 40 mol% and particularly preferably 10 to 30 mol% of alkyl vinyl ethers.
• the weight ratio of flow improver A to copolymer B is between 40:60 and 95: 5, preferably between 60:40 and 95: 5 and particularly preferably between 70:30 and 90:10.
• alkyl groups of the alkyl (meth) acrylates consist of 1 to 30, preferably 4 to 22 and particularly preferably 8 to 18 carbon atoms. They are preferably straight-chain and unbranched. However, up to 20% by weight of cyclic and / or branched portions can also be present.
• alkyl (meth) acrylates examples include n-octyl (meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate, n-tetradecyl (meth) acrylate, n-hexadecyl (meth) acrylate and n-octadecyl (meth) acrylate and mixtures thereof.
• ethylenically unsaturated dicarboxylic acids are maleic acid, tetrahydrophthalic acid, citraconic acid or itaconic acid or their anhydrides, fumaric acid and mixtures thereof.
• Maleic anhydride is preferred.
• alkyl vinyl ethers examples include octadecyl vinyl ether, eicosyl vinyl ether, docosyl vinyl ether, tetracosyl vinyl ether, hexacosyl vinyl ether and octacosyl vinyl ether and mixtures thereof.
• copolymers B show synergistic effects together with flow improvers. Although the copolymers B alone show little or no flow-improving effect, the combination of A and B far exceeds the individual efficacies.
• the carboxylic acid (anhydride) groups on the copolymer B can be completely or partially reacted with compounds containing amino or hydroxyl groups. This is not necessary to get the desired effectiveness. However, the effectiveness can be increased in some cases by the reaction and the solubility in the middle distillate or the compatibility with other components can be influenced favorably.
• Alkylamines are compounds containing amino groups preferably in which R1 is a straight-chain or branched alkyl radical having 1 to 30, preferably 8 to 26 and particularly preferably 12 to 24 carbon atoms and R2 is hydrogen, methyl or R1.
• R1 is a straight-chain or branched alkyl radical having 1 to 30, preferably 8 to 26 and particularly preferably 12 to 24 carbon atoms and R2 is hydrogen, methyl or R1.
• Ethylhexylamine, octadecylamine, oleylamine, tallow fatty amine, N-methyloctadecylamine and preferably behenylamine, dibehenylamine and hydrogenated ditallow fatty amine may be mentioned in particular.
• alkylaryl or aryl amines and cyclic amines which may have a hetero atom, can also be used.
• R1- (OR2) n -OH compounds containing hydroxyl groups R1- (OR2) n -OH wherein R1 is C1 to C30 alkyl, C6 to C12 aryl or C1 to C30 alkylaryl and R2 is C1 to C4 alkyl and n is an integer from 0 to 30, preferably.
• Examples of compounds containing hydroxyl groups include: alcohols such as 2-ethylhexanol, n-hexadecanol and n-octadecanol, alkylphenols such as iso-octylphenol, iso-nonylphenol and their reaction products with alkylene oxides such as ethylene oxide, propylene oxide and butylene oxide.
• Examples of flow improvers A are the polymers already mentioned, described in DE-A-21 02 469 and EP-A-84 148, such as copolymers of ethylene with vinyl acetate, vinyl propionate, vinyl butyrate, vinyl pivalate or with esters of (meth) acrylic acid, which are derived from alkanols with 1 to 12 carbon atoms.
• the alkyl (meth) acrylates are easily accessible. They can be obtained by the known esterification processes. For example, a solution of (meth) acrylic acid and an alkanol or one is heated Mixing various alkanols in an organic solvent with the addition of the usual polymerization inhibitors, for example hydroquinone derivatives and esterification catalysts such as sulfuric acid, p-toluenesulfonic acid or acidic ion exchangers at the boil and removes the water of reaction formed by azeotropic distillation.
• the usual polymerization inhibitors for example hydroquinone derivatives and esterification catalysts such as sulfuric acid, p-toluenesulfonic acid or acidic ion exchangers
• alkyl (meth) acrylates Further possibilities for the preparation of the alkyl (meth) acrylates are the reaction of (meth) acrylic acid chloride or anhydride with the corresponding alkanols and the known transesterification reaction of lower (meth) acrylic acid esters with the corresponding C8 to C18 alkanols with the addition of acidic or basic catalysts and distillative removal of the lower alkanol. In these production processes, too, the ester should be worked up to such an extent that no acid is present.
• the vinyl ethers can be obtained by known processes by reacting alkanols with acetaldehyde and subsequent elimination of water or by catalytic addition of acetylene to alkanols. Particularly pure monomers can also be obtained here by distillation. In the case of vinyl ethers with more than 20 to 22 carbon atoms in the alkyl part, the undecomposed distillation is technically difficult to carry out. In these cases, cleaning by filtration, extraction or recrystallization to remove the catalysts is recommended.
• the dicarboxylic acids in the form of the anhydrides, if available, in the copolymerization, e.g. Maleic anhydride, itaconic anhydride, citraconic anhydride and tetrahydrophthalic anhydride, since the anhydrides generally copolymerize better with the (meth) acrylates.
• the anhydride groups of the copolymers can then be reacted directly with compounds containing amino or hydroxyl groups.
• the reaction of the polymers with amines takes place at temperatures of 50 to 250 ° C in the course of 0.3 to 30 hours.
• the amine is used in amounts of about one to two moles per mole of polymerized dicarboxylic anhydride, ie about 0.9 to 2.1 moles / mole. The use of larger or smaller amounts is possible, but has no advantage.
• the usage of 2 moles of amine per mole of anhydride leads to the amide / ammonium salt. This can be converted into the diamide by heating to 150 to 200 ° C with elimination of water.
• 1 mole of a primary amine per mole of anhydride the resulting monoamide can be converted into the imide by heating to 150 to 250 ° C.
• the reaction of the polymers with alcohols, alkylphenols or their alkoxylates also takes place at temperatures of 50 to 250 ° C.
• the alcohol or the phenol are used in amounts of 1 to 2 moles per mole of anhydride. If 1 mole of alcohol is used, the half-ester is formed; with 2 moles of alcohol, an esterification catalyst has to be added and the water of reaction has to be removed so that the diester can be formed completely.
• the copolymers B can also be reacted both with an amino group-containing compound and with a hydroxyl group-containing compound. If the reaction is first carried out with an alcohol, then with an amine, an ester / ammonium salt is obtained, depending on the conditions, or an ester / amide at a higher temperature and removal of the water of reaction. If the reaction is first carried out with the amine, then with the alcohol, an ester / amide is obtained at the same time with removal of the water of reaction at a higher temperature.
• the copolymers B are prepared by known batch or continuous polymerization processes such as bulk, suspension, precipitation or solution polymerization and initiation with customary radical donors such as acetylcyclohexanesulfonyl peroxide, diacetyl peroxidicarbonate, dicyclohexyl peroxidicarbonate, di-2-ethylhexyl peroxidicylate, 2,2'-dodecarboxylate, tert.
• customary radical donors such as acetylcyclohexanesulfonyl peroxide, diacetyl peroxidicarbonate, dicyclohexyl peroxidicarbonate, di-2-ethylhexyl peroxidicylate, 2,2'-dodecarboxylate, tert.
• -Azobis (4-methoxy-2,4-dimethylvaleronitrile), tert-butyl perpivalate, tert-butyl per-2-ethylhexanoate, tert-butyl permaleinate, 2,2'-azobis (isobutyronitrile), bis (tert-butyl peroxide ) -cyclohexane, tert-butyl peroxyisopropyl carbonate, tert-butyl peracetate, di-cumyl peroxide, di-tert-amyl peroxide, di-tert-butyl peroxide, p-menthane hydroperoxide, cumene hydroperoxide or tert-butyl hydroperoxide and mixtures among themselves.
• these initiators are used in amounts of 0.1 to 20% by weight, preferably 0.2 to 15% by weight, based on the monomers.
• the polymerization is generally carried out at temperatures of 40 to 400 ° C., preferably 70 to 300 ° C., the use of solvents with boiling temperatures below the polymerization temperature advantageously being carried out under pressure.
• the polymerization is conveniently carried out in the absence of air, i.e. if it is not possible to work under boiling conditions, e.g. carried out under nitrogen or carbon dioxide, since oxygen delays the polymerization.
• the reaction can be accelerated by using redox coinitiators such as benzoin, dimethylaniline, ascorbic acid and organically soluble complexes of heavy metals such as copper, cobalt, manganese, iron, nickel and chromium.
• the amounts usually used are 0.1 to 2000 ppm by weight, preferably 0.1 to 1000 ppm by weight.
• regulators are, for example, allyl alcohols, such as 1-buten-3-ol, organic mercapto compounds, such as 2-mercaptoethanol, 2-mercaptopropanol, mercaptoacetic acid, mercaptopropionic acid, tert-butyl mercaptan, n-butyl mercaptan, n-octyl mercaptan, n-dodecyl mercaptan and tert.- Dodecyl mercaptan, which are generally used in amounts of 0.1 to 10 wt .-%.
• Equipment suitable for the polymerization is e.g. Conventional stirred kettles with, for example, armature, blade, impeller or multi-stage impulse countercurrent stirrers and for the continuous production of stirred kettle cascades, tubular reactors and static mixers.
• the simplest method of polymerization is bulk polymerization.
• the monomers are polymerized in the presence of an initiator and in the absence of solvents.
• all monomers are mixed in the desired composition and a small part, for example about 5 to 10%, is placed in the reactor, heated to the desired polymerization temperature with stirring and metered in the remaining monomer mixture and the initiator and, if appropriate, coinitiator and regulator within 1 to 10 hours, preferably 2 to 5 hours, evenly.
• the copolymer can then be converted into the flow improver according to the invention directly in the melt or after absorption in a suitable solvent.
• a continuous high-pressure process which permits space-time yields of 1 to 10 kg of polymer per liter of reactor and hour is also suitable for producing the desired copolymers.
• a polymerization apparatus e.g. a pressure vessel, a pressure vessel cascade, a pressure tube or a pressure vessel with a downstream reaction tube, which is provided with a static mixer, can be used.
• the monomers are preferably polymerized from (meth) acrylic esters, unsaturated dicarboxylic acids or their anhydrides and vinyl ethers in at least two polymerization zones connected in series.
• One reaction zone can consist of a pressure-tight vessel, the other of a heatable static mixer. You get sales of more than 99%.
• a copolymer of (meth) acrylic acid esters, maleic anhydride and octadecyl vinyl ether can be prepared, for example, by continuously feeding the monomers and a suitable initiator to a reactor or two reaction zones connected in series, for example a reactor cascade, and the reaction product after a residence time of 2 to 60 preferably from 5 to 30 minutes, at temperatures between 200 and 400 ° C. continuously discharged from the reaction zone.
• the polymerization is advantageously carried out at pressures of more than 1 bar, preferably between 1 and 200 bar.
• the copolymers obtained have solids contents of over 99%.
• Another simple method for producing the copolymers B is solution polymerization. It is carried out in solvents in which the monomers and the copolymers formed are soluble. All solvents which fulfill this requirement and which do not react with the monomers are suitable for this. For example, these are toluene, xylene, ethylbenzene, cumene, high-boiling aromatic mixtures such as Solvesso® 100, 150 and 200, aliphatic and cycloaliphatic hydrocarbons such as n-hexane, cyclohexane, methylcyclohexane, n-octane, iso-octane, paraffin oils, Shellsol® TD , T and K, as well as tetrahydrofuran and dioxane, tetrahydrofuran and dioxane being particularly suitable for achieving low molecular weight copolymers.
• the solution polymerization it is expedient to initially introduce solvent and part of the monomer mixture (for example about 5 to 20%) and to meter in the rest of the monomer mixture with the initiator and, if appropriate, coinitiator, regulator and solvent.
• the monomers can also be metered in individually at different rates. This is recommended for monomers with very different reactivities and if the distribution is particularly uniform of the less reactive monomer in the polymer is desired. The less reactive monomer is metered in faster and the more reactive monomer more slowly. It is also possible to introduce the entire amount of a monomer, preferably the less reactive anhydride or vinyl ether, and to meter in only the (meth) acrylate.
• polymers A and B should be present together in the form of a concentrate, since the use of 2 concentrates - one each for polymer A and polymer B - makes handling more difficult. Due to the possible incompatibility of polymers A and B, phase separation can occur when the two polymers are mixed in a common solvent. This can optionally be suppressed by suitable solvents and / or additives. Suitable are e.g.
• Alkanols such as iso-butanol, n-hexanol, 2-ethylhexanol, iso-decanol and their adducts with ethylene oxide, propylene oxide and / or butylene oxide, alkylphenols and their adducts with ethylene oxide, propylene oxide and / or butylene oxide as well as half esters or diesters of dicarboxylic acids with alkanols or (Oligo) alkylene oxide half ethers such as motto or dibutyl phthalate, mono- or di-2-ethylhexyl phthalate or di- (2-methoxyethyl) phthalate.
• Another method of avoiding possible phase separation is to graft copolymer B at least in part onto the flow improver.
• Bulk or solution polymerization is preferably used for the grafting.
• the polymerization can be carried out according to the "batch" or feed procedure.
• the entire amount of flow improver A to be grafted is initially introduced together with the monomers and initiator and, if appropriate, coinitiator and Regulator dosed.
• the total amount of flow improver A to be grafted is optionally introduced together with some of the monomers and the rest of the monomers, initiator and, if appropriate, coinitiator and regulator are metered in.
• the copolymer B As already mentioned, it is not necessary to graft the copolymer B onto the entire proportion of the flow improver A. For example, at a ratio A: B of 90:10, for reasons of space-time yield, the copolymer B will only be grafted to a proportion of 2 to 20% by weight of the total amount of A. With a ratio of A: B of 40:60, however, to a proportion of 30 to 100% by weight of the total amount of A.
• copolymer B may also be present in the concentrates described.
• the K values (according to H. Fikentscher, Cellulosechemie, Volume 13, pages 58 to 64 and 71 to 74 (1932)), determined in 2% (w / v) xylene solution of the copolymers B, are between 10 and 50 , preferably between 10 and 40 and particularly preferably between 13 and 30.
• the particularly preferred range corresponds to molecular weights between approximately 5000 and 25,000 g / mol (number average values, determined by gel permeation chromatography against polystyrene standards).
• the additives A and B according to the invention are added to the petroleum middle distillates in amounts of altogether 50 to 5000 ppm, preferably 100 to 2000 ppm.
• the middle distillates according to the invention containing small amounts of a flow improver A and a copolymer B, can, depending on the intended use, other additives or additives such as dispersants, anti-foam additives, corrosion inhibitors, antioxidants, dyes and others. contain.
• a clear, light yellow, viscous, about 50% by weight polymer solution was obtained.
• the K value of the polymer was 30.6; the molar ratio of acrylate to maleic anhydride to vinyl ether is approximately 80:10:10.
• Example 1 In a reactor according to Example 1 was 104.4 g of a C18- to C22-alkyl vinyl ether (made from a commercially available fatty alcohol mixture consisting of a maximum of 41 to 43 wt .-% n-octadecanol, 9 to 13 wt .-% n-eicosanol , 43 to 46% by weight of n-docosanol), 29.8 g of maleic anhydride and 185 g of Shellsol® K in a gentle stream of nitrogen with stirring to 100 ° C. and heated with 50 g of a solution of 375 g of lauryl acrylate in 202 g of Shellsol® K added and the rest of the solution metered in evenly within 2 hours.
• a C18- to C22-alkyl vinyl ether made from a commercially available fatty alcohol mixture consisting of a maximum of 41 to 43 wt .-% n-octadecanol, 9 to 13
• an n-alkyl acrylate mixture prepared from a commercially available fatty alcohol mixture of the following composition, was used: 5 to 8 wt.% N-octanol, 5 to 7 wt.% N-decanol, 44 to 50 wt.% N-dodecanol, 14 to 20 wt.% N-tetradecanol, 8 to 10 wt. % n-hexadecanol and 8 to 12% by weight n-octadecanol.
• a clear, light yellow, viscous, about 50% by weight polymer solution was obtained.
• the K value of the polymer was 18.5; the molar ratio of acrylate to maleic anhydride to vinyl ether is about 70:15:15.
• Example 5 but 94 g of n-octadecyl vinyl ether were used instead of the C18 to C22 vinyl ether. A clear, light yellow, viscous, about 50% by weight polymer solution was obtained. The K value of the polymer was 20.3; the molar ratio of acrylate to maleic anhydride to vinyl ether is about 70:15:15.
• the flow improvers FI (A) and FI (B) are commercially available products, e.g. the Keroflux® brands from BASF.
• Middle distillate I Heating oils and diesel fuels in commercial West German refinery quality were used as middle distillates. They are referred to as middle distillate I, II, III and IV. Middle distillate I. II III IV Cloud point (° C) + 6 + 2 + 4th + 5 CFPP (° C) 0 - 3rd - 1 - 2nd Initial boiling point (° C) 155 175 169 174 20% boiling point (° C) 232 247 222 219 50% boiling point (° C) 280 285 262 272 90% boiling point (° C) 352 354 351 365 End of boiling point (° C) 382 375 381 385

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Cited By (9)

Citations (9)

• 1990
  • 1990-11-14 DE DE4036226A patent/DE4036226A1/de not_active Withdrawn
• 1991
  • 1991-10-24 ES ES91118117T patent/ES2049072T3/es not_active Expired - Lifetime
  • 1991-10-24 DE DE91118117T patent/DE59101025D1/de not_active Expired - Lifetime
  • 1991-10-24 EP EP91118117A patent/EP0485774B1/fr not_active Expired - Lifetime
  • 1991-10-24 AT AT91118117T patent/ATE101640T1/de not_active IP Right Cessation
  • 1991-10-30 FI FI915127A patent/FI915127A/fi unknown
  • 1991-11-13 NO NO91914444A patent/NO914444L/no unknown
  • 1991-11-13 CA CA002055417A patent/CA2055417A1/fr not_active Abandoned

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