WO2004035715A1 - Utilisation d'homopolymères d'éther vinylique hydrocarbyle pour améliorer l'effet de promoteurs d'écoulement à froid - Google Patents

Utilisation d'homopolymères d'éther vinylique hydrocarbyle pour améliorer l'effet de promoteurs d'écoulement à froid Download PDF

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WO2004035715A1
WO2004035715A1 PCT/EP2003/011309 EP0311309W WO2004035715A1 WO 2004035715 A1 WO2004035715 A1 WO 2004035715A1 EP 0311309 W EP0311309 W EP 0311309W WO 2004035715 A1 WO2004035715 A1 WO 2004035715A1
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fuel oil
cold flow
use according
component
fuel
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PCT/EP2003/011309
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German (de)
English (en)
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Wolfgang Ahlers
Uwe Rebholz
Jan Van Trier
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Basf Aktiengesellschaft
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Priority to AT03748128T priority Critical patent/ATE430186T1/de
Priority to AU2003267442A priority patent/AU2003267442A1/en
Priority to CN200380101356.4A priority patent/CN1705734B/zh
Priority to DE50311484T priority patent/DE50311484D1/de
Priority to EP03748128A priority patent/EP1554365B1/fr
Publication of WO2004035715A1 publication Critical patent/WO2004035715A1/fr

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Definitions

  • the present invention relates to the use of hydrocarbyl vinyl ether homopolymers to improve the effect of cold flow improvers for fuel oil compositions.
  • the invention further relates to the use of an additive which comprises such a polymer and a customary cold flow improver for reducing the CFPP value and, if appropriate, furthermore for reducing the CFPP2 value and / or the aspiration value of a fuel oil composition.
  • Mineral oils and crude oils containing paraffinic waxes show a marked deterioration in the flow properties when the temperature is lowered.
  • the reason for this lies in the crystallization of long-chain paraffins which occur from the temperature of the cloud point (cloud point) and form large platelet-shaped wax crystals. These wax crystals have a sponge-like structure and lead to the inclusion of other fuel components in the crystal composite.
  • additives have been added to the mineral oils and crude oils in small concentrations for a long time, which often consist of a combination of nucleators with the actual cold flow improvers.
  • Nucleators are substances that generate crystal nuclei that promote the formation of tiny crystals.
  • Cold flow improvers have similar crystallization properties to the paraffins contained in mineral oil or crude oil, but prevent their growth.
  • the crude and mineral oils are wax Anti-settling additives (WASA) added to prevent the tiny crystals from sinking into the oils.
  • WASA wax Anti-settling additives
  • CFPP Cold Filter Plugging Point
  • EP-A-0 360 419 describes additives for improving the cold flow properties of fuel compositions which contain homo- or copolymers of alkyl vinyl ethers and, if appropriate, other customary cold flow improvers.
  • DE-A-2 047 448 describes an additive mixture of polyvinyl ethers with ethylene-vinyl acetate copolymers to improve the pumpability of crude oils. The use in fuel oils is not described.
  • a disadvantage of the additives of the prior art is that they sometimes do not, or only slightly, reduce the CFPP value of fuel oils.
  • the prior art does not describe any additives which have an effect on the CFPP2 and / or aspiration value of the fuel oils.
  • the object of the present invention was therefore to further improve the effect of conventional cold flow improvers.
  • the additive should improve the effect of the cold flow improvers on reducing the CFPP value of fuel oil compositions and, if appropriate, lead to a reduction or elimination of the CFPP2 values and / or to avoid aspiration effects.
  • the object was achieved by using a homopolymer of a hydrocarbyl vinyl ether to improve the effect of cold flow improvers for fuel oil compositions.
  • hydrocarbyl is understood as a hydrocarbon radical which is bonded to the ether function of the vinyl ether via a carbon atom.
  • the hydrocarbon radical can be, for example, an aliphatic radical, such as alkyl and alkenyl, which is optionally substituted by at least one aromatic and / or alicyclic radical, an alicyclic radical, such as cycloalkyl or cycloalkenyl, which may optionally be substituted by at least one aromatic and / or aliphatic Radical is substituted, or an aromatic radical which is optionally substituted with at least one aliphatic and / or alicyclic radical.
  • the aliphatic and alicyclic radicals can be interrupted by at least one group 0, S, NR 5 , or CO.
  • the hydrocarbon radical can furthermore be substituted by at least one radical such as OR 5 , SR 5 , NR 5 R 6 , COR 5 , COOR 5 or CONR 5 R 6 , the radicals R 5 and R 6 being as defined below. - ⁇ • ⁇ •
  • the homopolymer of hydrocarbyl vinyl ether preferably has the following structural formula I:
  • R 1 for C 1 -C 4 -alkyl which is optionally interrupted by one or more groupings which are selected from CO, NR 5 , 0 and S, and / or by one or more Radicals which are selected from NR 5 R 6 , OR 5 , SR 5 , COR 5 , COOR 5 , CONR 5 R 6 and aryl, or are aryl,
  • R 2 , R 3 and R 4 each independently represent H or C 1 -C 4 -alk l,
  • R 5 and R 6 are each independently of one another H or C 1 -C 4 -alkyl and
  • n stands for a number from 2 to 3000.
  • radicals R 1 , R 2 , R 3 and R 4 -C 1 -C 4 o-alkyl 'is in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert- Butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eggcosyl, docosyl, tricosyl, tetracosyl, pentac Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Squalyl and the higher homologues
  • C 1 -C 4 alkyl is in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl.
  • aryl is preferably C 6 -C 4 -aryl, such as phenyl, naphthyl, anthracenyl and phenanthryl, the aryl radical being optionally by one or more radicals selected from C 1 -C 4 o-alkyl, OR 5 , SR 5 , NR 5 R 6 , COOR 5 , CONR 5 R 6 " 'and aryl.
  • R 1 is preferably C ⁇ -C 4 -alkyl, particularly preferably C ⁇ -C 3 -alkyl and in particular C 2 -C 22 alkyl.
  • the alkyl radical is preferably not very branched or linear, in particular linear. Furthermore, the alkyl radical is neither interrupted nor substituted by the groups listed above.
  • R 2 , R 3 and R 4 are preferably H.
  • Preferred compounds of the formula I also have a number-average molecular weight Mn in the range from about 1000 to 20,000, in particular 2,000 to 20,000, preferably 3,000 to 15,000.
  • the cold flow improvers are preferably selected from a) copolymers of ethylene with at least one further ethylenically unsaturated monomer;
  • the monomer is preferably selected from alkenyl carboxylic acid esters, (meth) acrylic acid esters and olefins.
  • Suitable olefins are, for example, those with 3 to 10 carbon atoms and with 1 to 3, preferably with 1 or 2, in particular with one, carbon-carbon double bond. In the latter case, the carbon-carbon double bond can be arranged both terminally ( ⁇ -olefin) and internally.
  • ⁇ -olefins particularly preferably ⁇ -olefins having 3 to 6 carbon atoms, such as propene, 1-butene, 1-pentene and 1-hexene.
  • Suitable (meth) acrylic acid esters are, for example, esters of (meth) acrylic acid with Ci-Cio-alkanols, in particular with methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert-butanol, pentanol, hexanol, Heptanol, octanol, 2-ethyl 'hexanol, nonanol and decanol.
  • Suitable alkenyl carboxylic acid esters are, for example, the vinyl and propenyl esters of carboxylic acids having 2 to 20 carbon atoms, the hydrocarbon radical of which can be linear or branched. Among these, the vinyl esters are preferred. Among the carboxylic acids with branched hydrocarbon radical, those are preferred whose branch is in the ⁇ position to the carboxyl group, the ⁇ carbon atom being particularly preferably tertiary, ie the carboxylic acid being a so-called neocarboxylic acid. However, the hydrocarbon residue of the carboxylic acid is preferably linear.
  • alkenyl carboxylic acid esters examples include vinyl acetate, vinyl propiona, vinyl butyrate, vinyl neopentanoate, vinyl hexanoate, vinyl neononanoate, vinyl neodecanoate and the corresponding propenyl esters, with the vinyl esters being preferred.
  • a particularly preferred alkenyl carboxylic acid ester is vinyl acetate.
  • the ethylenically unsaturated monomer is particularly preferably selected from alkenyl carboxylic acid esters.
  • Copolymers which contain two or more different alkenyl carboxylic acid esters in copolymerized form are also suitable, these differing in the alkenyl function and / or in the carboxylic acid group. Also suitable are copolymers which, in addition to the alkenyl carboxylic acid ester (s), contain at least one olefin and / or at least one (meth) acrylic acid ester in copolymerized form.
  • the ethylenically unsaturated monomer is copolymerized in the copolymer in an amount of preferably 1 to 30 mol%, particularly preferably 1 to 25 mol% and in particular 5 to 20 mol%, based on the total copolymer.
  • the copolymer a) preferably has a number average molecular weight M n of 500 to 20,000, particularly preferably of 1,000 to 15,000.
  • Comb polymers b) are, for example, those described in "Comb-Like Polymers. Structure and Properties", N.A. Plat and V.P. Shibaev, J. Poly. Be. Macromolecular Revs. 8, pages 117 to 253 (1974). Of the compounds described there, comb polymers of the formula II are suitable, for example
  • D represents R 7 , COOR 7 , OCOR 7 , R 8 , COOR 7 or OR 7 ,
  • E represents H, CH 3 , D or R 8 ,
  • G represents H or D
  • J represents H, R 8 , R 8 COOR 7 'aryl or heterocyclyl
  • K represents H, COOR 8 , OCOR 8 , OR 8 or COOH
  • L represents H, R 8 , COOR 8 , OCOR 8 , COOH or aryl
  • R 7 represents a hydrocarbon radical with at least 10 carbon atoms, preferably with 10 to 30 carbon atoms,
  • R 8 represents a hydrocarbon radical with at least one carbon atom, preferably with 1 to 30 carbon atoms,
  • m stands for a mole fraction in the range from 1.0 to 0.4
  • n stands for a mole fraction in the range from 0 to 0.6.
  • Preferred comb polymers are, for example, by copolymerizing maleic anhydride or fumaric acid with another ethylenically unsaturated monomer, for example with an ⁇ -olefin or an unsaturated ester, such as vinyl acetate, and then esterifying the anhydride or acid function with an alcohol having at least 10 carbon atoms available.
  • Further preferred comb polymers are copolymers of a-olefins and esterified ⁇ comonomers, for example esterified copolymers of styrene and maleic anhydride or esterified copolymers of styrene and fumaric acid. Mixtures of comb polymers are also suitable.
  • Comb polymers can also be polyfumarates or polymaleates.
  • Suitable polyoxyalkylenes c) are, for example, polyoxyalkylene esters, ethers, esters / ethers and mixtures thereof.
  • the polyoxyalkylene compounds preferably contain at least one, particularly preferably at least two linear alkyl groups with 10 to 30 carbon atoms and a polyoxyalkylene group with a molecular weight of up to 5000.
  • the alkyl group of the polyoxyalkylene radical preferably contains 1 to 4 carbon atoms.
  • Such polyoxyalkylene compounds are described, for example, in EP-A-0 061 895 and in US 4,491,455, which are hereby incorporated by reference in their entirety.
  • Preferred polyoxyalkylene esters, ethers and esters / ethers have the general formula III wherein
  • R 9 and R 10 each independently represent R 11 , RH-CO-, R 11 _0-CO (CH 2 ) z - or R H -0-CO (CH 2 ) z -CO-,
  • R 11 represents linear C 1 -C 3 -alkyl
  • y represents a number from 1 to 4,
  • x represents a number from 2 to 200
  • z represents a number from 1 to 4.
  • Preferred polyoxyalkylene compounds of the formula III in which both R 9 and R 10 are R 11 are polyethylene glycols and polypropylene glycols with a number average molecular weight of 100 to 5000.
  • Preferred polyoxyalkylenes of the formula III in which one of the radicals R 9 and R 10 are R 11 and the other stands for R 1: 1 -CO- are polyoxyalkylene esters of fatty acids with 10 to 30 carbon atoms, such as stearic acid or behenic acid.
  • Preferred polyoxyalkylene compounds in which both R 9 and R 10 stand for a radical R —CO— are diesters of fatty acids with 10 to; Carbon atoms, preferably stearic or behenic acid.
  • the polar nitrogen compounds d), suitably öllös lent are 'can both ionically and non-be nonionic and preferably have at least one, more preferably at least 2 substituents of the formula> NR 12 wherein R 12 is a C 8 -C 4 o -Carbon residue stands.
  • the nitrogen substituents can also be quaternized, that is to say in cationic form.
  • An example of such nitrogen compounds are ammonium salts and / or amides which can be obtained by reacting at least one amine substituted with at least one hydrocarbon radical with a carboxylic acid having 1 to 4 carboxyl groups or with a suitable derivative thereof.
  • the amines preferably contain at least a linear Cs-C 4 o-alkyl radical.
  • Suitable primary amines are, for example, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tetradecylamine and the higher linear homologues.
  • Suitable secondary amines are, for example, dioctadecylamine and methylbehenylamine.
  • Amine mixtures in particular amine mixtures accessible on a large industrial scale, such as fatty amines or hydrogenated tallamines, as described, for example, in Ull ann's Encyclopedia of Industrial Chemistry, 6th edition, 2000 electronic release, chapter "Airlines, aliphatic", are also suitable. the.
  • Acids suitable for the reaction are, for example, cyclohexane-1,2-dicarboxylic acid, cyclohexene-1,2-dicarboxylic acid, cyclopentane-1,2-dicarboxylic acid, naphthalenedicarboxylic acid, phthalic acid, isophthalic acid, terephthalic acid and succinic acids substituted with long-chain hydrocarbon radicals ,
  • A stands for a linear or branched aliphatic hydrocarbon group, which may be replaced by one or more groups selected from O , S, NR and CO, is interrupted, and R 13 and R 14 stand for a C 9 -C 4 o-hydrocarbon residue which may be replaced by one or more groups selected from 0, S, NR 5 and CO , interrupted and / or substituted by one or more substituents selected from OH, SH and NR 5 R 6 , where R 5 and R 6 are as defined above.
  • A is preferably a methylene or polymethylene group having 2 to 20 methylene units.
  • radicals R 13 and R 14 are 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 2-ketopropyl, ethoxyethyl and propoxypropyl.
  • the cyclic system can be homocyclic, heterocyclic, condensed polycyclic or uncondensed polycyclic systems.
  • the ring system is preferably carbo- or heteroaromatic, in particular carboaromatic.
  • polycyclic ring systems examples include condensed benzoid structures, such as naphthalene, anthracene, phenanthrene and pyrene, condensed nonbenzoic structures, such as azulene, indene, hydrindenes and fluorene, uncondensed polycycles, such as diphenyl, heterocycles, such as quinoline, indole, Dihydroindole, benzofuran, coumarin, isocoumarin, benzthiophene, carbazole, diphenylene oxide and diphenylene sulfide, non-aromatic or partially saturated ring systems such as decalin, and three-dimensional structures such as ⁇ -pinene, camphene, bornylene, norbonane, norbornene, bicyclooctane and bicyclooctene.
  • condensed benzoid structures such as naphthalene, anthracene, phenanthrene and pyren
  • Suitable polar nitrogen compounds are condensates of long-chain primary or secondary amines with carboxyl group-containing ⁇ Polymeren.-
  • Suitable polar nitrogen compounds are also described, for example, in DE-A-198 48 621, DE-A-196 22 052 or EP-B-398 101, to which reference is hereby made.
  • Suitable sulfocarboxylic acids / sulfonic acids or their derivatives e) are, for example, those of the general formula IV
  • R 15 represents a hydrocarbon radical
  • R 16 and R 17 represent alkyl, alkoxyalkyl or polyalkoxyalkyl with at least 10 carbon atoms in the main chain,
  • R 18 represents C ⁇ -C 5 alkylene
  • a and B represent alkyl, alkenyl or two substituted hydrocarbon radicals or together with the carbon atoms to which they are attached form an aromatic or cycloaliphatic ring system.
  • Suitable poly (meth) acrylic acid esters f) are both homo- and copolymers of acrylic and methacrylic acid esters. Copolymers of at least two mutually different (meth) acrylic acid esters which differ with respect to the condensed alcohol are preferred. If appropriate, the copolymer contains a further, different olefinically unsaturated mono- polymerized. The weight average molecular weight of the polymer is preferably 50,000 to 500,000.
  • a particularly preferred polymer is a copolymer of methacrylic acid and methacrylic acid esters of saturated C 14 and cis alcohols, the 5 acid groups being neutralized with hydrogenated tallamine. Suitable poly (meth) acrylic acid esters are described, for example, in WO 00/44857, to which reference is hereby made in full.
  • copolymers of ethylene with at least one further ethylenically unsaturated monomer a) are used as cold flow improvers.
  • preferred copolymers reference is made to the statements made above.
  • Mixtures of copolymers a) with at least one of the cold flow improvers b) to f) are also suitable.
  • Fuel oil compositions are preferably understood to mean fuels. Suitable fuels are petrol and middle distillates, such as diesel fuels, heating oil or kerosene, with diesel fuel and heating oil being preferred.
  • the heating oils are, for example, low-sulfur or high-sulfur petroleum refines or stone or brown coal
  • the heating oils 1 are preferably low-sulfur heating oils, for example those with a sulfur content of at most 0.1% by weight, preferably at most 0.05% by weight, particularly preferably at most 0.005% by weight, and INS
  • Diesel fuels are, for example, petroleum raffinates, which usually have a boiling range of 100 to 400 ° C. These are mostly distillates with a 95% point up to
  • the additive mixture according to the invention is particularly preferred for the additivation of diesel fuels with a low sulfur content, that is to say with a sulfur content of less than 0.05% by weight, preferably less than 0.02% by weight, in particular less than 0.005% by weight. % and especially less than 0.001% by weight sulfur or for the additive of heating oil with a low sulfur content, for example with a sulfur content of at most 0.1% by weight, preferably at most 0.05% by weight, particularly preferably at most 0.005 % By weight, and in particular of at most 0.001% by weight, is used.
  • the hydrocarbyl vinyl ether hemopolymer (activity improver) is preferably used in a proportion, based on the total amount of the fuel oil composition, which per se has essentially no influence on the cold flow properties of the fuel oil compositions.
  • the activity enhancer is particularly preferably used in an amount of 0.0001 to 0.005% by weight, in particular 0.0001 to 0.001% by weight, based on the total amount of the fuel oil composition.
  • the weight ratio of effect improver to cold flow improver is preferably 1: 1 to 1: 500, particularly preferably 1: 4 to 1: 500, even more preferably 1: 9 to 1: 500, in particular 1:19 to 1: 500 and especially 1:24 up to 1: 200.
  • Another object of the present invention is the use of an additive mixture comprising
  • component A at least one homopolymer of a hydrocarbyl vinyl ether
  • component B at least one conventional cold flow improver
  • Another object of the present invention is the use of an additive mixture comprising i) as component A at least one homopolymer of a hydrocarbyl vinyl ether and
  • component B at least one conventional cold flow improver
  • component A to component B with a weight ratio of component A to component B of 1: 1 to 1: 500 for the additive of fuel oil compositions.
  • the additive mixtures used according to the invention preferably serve to improve the cold flow properties of fuel oil compositions, such as, for example, lowering the cloud point, the pour point, the viscosity and in particular the CFPP value.
  • the present invention furthermore relates to an additive mixture comprising
  • weight ratio of component A to component is 1: 5 to 1: 500.
  • the weight ratio of component A to component B is preferably 1: 9 to 1: 500, particularly preferably 1:15 to 1: 500, even more preferably 1:20 to 1: 500 and especially 1:24 to 1: 200.
  • the present invention also relates to a fuel oil composition
  • a fuel oil composition comprising a major amount of a hydrocarbon fuel and an effective amount of an additive mixture as defined above and optionally at least one further customary additive.
  • an additive mixture as defined above and optionally at least one further customary additive.
  • the subject of the present application is an additive concentrate containing an additive mixture as defined above and at least one diluent and optionally at least one further additive.
  • Suitable diluents are, for example, fractions obtained in petroleum processing, such as kerosene, naphtha or
  • Aromatic and aliphatic hydrocarbons and alkoxyalkanols are also suitable.
  • middle distillates particularly preferred diluents for diesel fuels and heating oils, naphtha, kerosene, diesel fuels, aromatic hydrocarbons, such as heavy solvent naphtha, Solvesso or Shellsol R, and mixtures of these solvents and diluents.
  • the additive mixture according to the invention is preferably present in the concentrates in an amount of 0.1 to 80% by weight, particularly preferably 1 to 70% by weight and in particular 20 to 60% by weight, based on the total weight of the concentrate, in front.
  • Suitable additives which may be present in the fuel or concentrate according to the invention in addition to the additive mixtures according to the invention, in particular for diesel fuels and heating oils, include detergents, corrosion inhibitors, dehazers, demulsifiers, antifoams ("antifoam”), antioxidants, metal deactivators, multifunctional stabilizers, cetane number improvers, combustion improvers, dyes, markers, solubilizers, antistatic agents, lubricity improvers, additives other than the abovementioned which improve the cold properties, such as flow improvers ("MDFI"), paraffin dispersants (“WASA”) and the combination of the latter two Additives (“WAFI").
  • MDFI flow improvers
  • WASA paraffin dispersants
  • hydrocarbyl vinyl ether homopolymers leads to an improved effect of conventional cold flow improvers on the cold flow properties of fuel oil compositions, in particular to a more effective reduction in the CFPP value.
  • the cold flow improvers can be used in significantly smaller quantities than previously required.
  • MDFI 1 ethylene-vinyl acetate-based polymer mixture (Keroflux 3283)
  • MDFI 2 ethylene-vinyl acetate-based polymer mixture (Keroflux ES 40 6103)
  • MDFI 3 ethylene-vinyl acetate-based polymer mixture (Keroflux ES 6305)
  • MDFI 4 ethylene-vinyl acetate-based polymer mixture (Keroflux ES 6309)
  • MDFI 5 ethylene-vinyl acetate-based polymer mixture (Keroflux ES 6100)
  • MDFI 6 ethylene-vinyl acetate-based polymer mixture (Keroflux ES 5 6204)
  • MDFI 7 ethylene-vinyl acetate-based polymer mixture (Keroflux ES 6203)
  • MDFI 9 ethylene-vinyl acetate-based polymer mixture (Keroflux ES 6310) 5
  • PVE polyvinyl ethers
  • PVE 2 10% by weight solution of polyoctadecyl vinyl ether / polystyrene vinyl ether mixture (85/15) in Solvesso 150
  • the effect improvers PVE 1 to 4 were used in an amount of 1 to 4% by weight of pure substance, based on the amount of cold flow improver.
  • the CFPP values were determined in accordance with EN 116.
  • a commercially available automatic CFPP analysis device e.g. available from WalterHerzog GmbH, Lauda-Koenigshofen, Germany, type MP842. Also compare the operating instructions for determining the CFPP 2 value.

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  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • Liquid Carbonaceous Fuels (AREA)
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  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne l'utilisation d'homopolymères d'éther vinylique hydrocarbyle pour améliorer l'effet de promoteurs d'écoulement à froid pour des compositions de combustibles. La présente invention porte également sur l'utilisation d'un additif comportant un polymère de ce type et un promoteur d'écoulement à froid usuel pour diminuer la valeur CFPP (température limite de filtrabilité des gazoles) et réduire éventuellement aussi la valeur CFPP2 et/ou la valeur d'aspiration d'une composition de combustible.
PCT/EP2003/011309 2002-10-14 2003-10-13 Utilisation d'homopolymères d'éther vinylique hydrocarbyle pour améliorer l'effet de promoteurs d'écoulement à froid WO2004035715A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AT03748128T ATE430186T1 (de) 2002-10-14 2003-10-13 Verwendung von hydrocarbylvinyletherhomopolymeren zur verbesserung der wirkung von kaltfliessverbesserern
AU2003267442A AU2003267442A1 (en) 2002-10-14 2003-10-13 Use of ether vinyl hydrocarbyl homopolymers for increasing effect of a cold flow improving agent
CN200380101356.4A CN1705734B (zh) 2002-10-14 2003-10-13 醚乙烯基烃基均聚物用于提高冷流改进剂的效用的用途
DE50311484T DE50311484D1 (de) 2002-10-14 2003-10-13 Verwendung von hydrocarbylvinyletherhomopolymeren zur verbesserung der wirkung von kaltfliessverbesserern
EP03748128A EP1554365B1 (fr) 2002-10-14 2003-10-13 Utilisation d'homopolymères d' éther vinylique hydrocarbyle pour améliorer l'effet de promoteurs d' écoulement à froid

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DE10247795.7 2002-10-14
DE10247795A DE10247795A1 (de) 2002-10-14 2002-10-14 Verwendung von Hydrocarbylvinyletherhomopolymeren zur Verbesserung der Wirkung von Kaltfliessverbesserern

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KR (1) KR101092726B1 (fr)
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DE (2) DE10247795A1 (fr)
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WO2018057694A2 (fr) 2016-09-21 2018-03-29 The Lubrizol Corporation Constituants polyacrylates antimousse destinés à être utilisés dans des carburants diesel
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DE102010001408A1 (de) 2009-02-06 2010-08-12 Basf Se Verwendung von Ketonen als Kraftstoffzusatz zur Verringerung des Kraftstoffverbrauches von Dieselmotoren
DE102010039039A1 (de) 2009-08-24 2011-03-03 Basf Se Verwendung von organischen Verbindungen als Kraftstoffzusatz zur Verringerung des Kraftstoffverbrauchs von Dieselmotoren
WO2011134923A1 (fr) 2010-04-27 2011-11-03 Basf Se Terpolymère quaternisé
US8790426B2 (en) 2010-04-27 2014-07-29 Basf Se Quaternized terpolymer
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EP1554365B1 (fr) 2009-04-29
AU2003267442A1 (en) 2004-05-04
KR20050061537A (ko) 2005-06-22
KR101092726B1 (ko) 2011-12-09
DE50311484D1 (de) 2009-06-10
CN1705734A (zh) 2005-12-07
CN1705734B (zh) 2011-07-27
ATE430186T1 (de) 2009-05-15
EP1554365A1 (fr) 2005-07-20
DE10247795A1 (de) 2004-04-22
ES2323686T3 (es) 2009-07-23

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