EP0061894A2 - Additif à deux composants pour améliorer l'écoulement des huiles combustibles distillats moyens - Google Patents

Additif à deux composants pour améliorer l'écoulement des huiles combustibles distillats moyens Download PDF

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Publication number
EP0061894A2
EP0061894A2 EP82301556A EP82301556A EP0061894A2 EP 0061894 A2 EP0061894 A2 EP 0061894A2 EP 82301556 A EP82301556 A EP 82301556A EP 82301556 A EP82301556 A EP 82301556A EP 0061894 A2 EP0061894 A2 EP 0061894A2
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EP
European Patent Office
Prior art keywords
vinyl acetate
nitrogen compound
flow
oil
soluble nitrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP82301556A
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German (de)
English (en)
Other versions
EP0061894B1 (fr
EP0061894A3 (en
Inventor
Robert Dryden Tack
Brian William Davies
Kenneth Lewtas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Filing date
Publication date
Application filed by Exxon Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to AT82301556T priority Critical patent/ATE15496T1/de
Publication of EP0061894A2 publication Critical patent/EP0061894A2/fr
Publication of EP0061894A3 publication Critical patent/EP0061894A3/en
Application granted granted Critical
Publication of EP0061894B1 publication Critical patent/EP0061894B1/fr
Expired legal-status Critical Current

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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
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • 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

Definitions

  • This invention relates to the use of certain mixtures of additives to improve the flow and filterability properties of distillate fuels at low temperatures to fuels containing the mixtures and to concentrates of the additives for incorporation into the fuel.
  • the invention relates to an additive system composed of a nitrogen-containing wax crystal growth inhibitor and a particular category of ethylene-vinyl acetate copolymer.
  • additives are disclosed in the art for improving the flow properties of middle distillate fuel oils.
  • Combinations of additives which function both as wax nucleators and/or wax crystal growth stimulators and as wax growth arrestors are well-known and disclosed for example in U.S. Patent 3,961,916 issued June 8th 1976 to Ilnyckyj et al, which shows an additive combination comprising ethylene copolymerised with ethylenically unsaturated mono- or dicarboxylic acid alkyl esters or a vinyl ester of a C 1 -C 17 saturated fatty acid.
  • Additive systems comprising nitrogen containing amide or amine salts as used in the present invention are disclosed in U.S. Patent 4,211,534 issued July 8th, 1980 to Feldman which discloses a three component combination additive flow improver consisting of an ethylene polymer or copolymer, a second polymer of an oil soluble ester and/or C 3 and higher olefin polymer and, as a third component, a nitrogen containing compound.
  • This three component system is said to have advantages over combinations consisting of any two of the additive components for improving the cold flow properties of distillate fuels.
  • U.S. Patent 3,982,909 issued September 28th, 1976 to Hollyday discloses an additive system comprising amides, diamides and ammonium salts alone or in combination with certain hydrocarbons such as microcrystalline waxes or petrolatums and/or an ethylene backbone polymeric pour depressant, the combination being useful as a flow improver for middle distillate fuels.
  • Nitrogen containing oil soluble succinic acid or its derivatives are disclosed in U.S. Patent 4,147,520 issued April 3, 1975 to Ilynckyj which describes these materials in combination with ethylene vinyl acetate copolymer wax nucleators.
  • the present invention is based on the discovery that a two component additive system consisting essentially of an amine salt that is an alkyl ammonium or amide compound having a total of 30-200 preferably 50-150 carbon atoms derived from certain carboxylic acids or anhydrides in combination with a certain ethylene vinyl acetate copolymer is highly effective at relatively lower treatment levels for improving the flow and filterability properties of middle distillate fuels below their cloud points.
  • wax containing petroleum fuel oil compositions comprising a wax containing middle distillate fuel oil, boiling in the range of about 120°C-500°C, which has been improved in its low temperature properties by the addition of 0.005 to 0.5 wt.%, preferably 0.005 to 0.25 wt.% of a flow and filterability improver consisting essentially of:
  • the flow improver combination of the present invention is useful in a broad category of distillate fuels boiling in the range of about 120°C to about 500°C (ASTM D1160), preferably those distillate fuels boiling in the range of about 150°C-400°C.
  • the invention is especially applicable to fuels which have a relatively high final boiling point (FB P ), that is, above 360°C.
  • the nitrogen containing wax crystal growth inhibitors used in the present invention are generally those having a total of 30-300, preferably 50-150 carbon atoms and being those oil-soluble amine salts and amides formed by reacting at least 1 molar portion of a hydrocarbyl substituted amine with 1 molar portion of the aromatic or cycloaliphatic polycarboxylic acid, e.g. 2 to 4 carboxyl groups preferably dicarboxylic acids, or their anhydrides or partial esters of dicarboxylic e.g. mono-esters of dicarboxylic acids.
  • the amines may be primary, secondary, tertiary or quaternary, but preferably are secondary. Tertiary and quaternary amines can only form amine salts. Examples of amines include tetradecyl amine, cocoamine, hydrogenated tallow amine and the like. Examples of secondary amines include cocomethyl amine, dioctadecyl amine, methyl-benhenyl amine and the like. Amine mixtures are also suitable and many amines derived from natural materials are mixtures.
  • the preferred amine is a secondary hydrogenated tallow amine of the formula HNR 1 R 2 wherein R 1 and R 2 are alkyl groups derived from tallow fat composed of approximately 4% C 14 , 31% C 16 , 59% C 18 .
  • carboxylic acids examples include cyclohexane dicarboxylic acid, cyclohexene dicarboxylic acid, cyclopentane dicarboxylic acid, naphthalene dicarboxylic acid, and the like. Generally these acids will have about 5-13 carbon atoms in the cyclic moiety.
  • Preferred acids useful in the present invention are benzene dicarboxylic acids such as phthalic acid, terephthalic acid, and isophthalic acid. Isophthalic acid or its anhydride is the particularly preferred embodiment.
  • the nitrogen containing compound has at least one straight chain alkyl segment extending from the compound containing 8-40 preferably 14-24 carbon atoms.
  • the nitrogen compound contains at least three alkyl chains each containing from 8 to 40 carbon atoms and preferably at least two of these chains are normal.
  • at least one ammonium salt, amine salt or amide linkage is required to be present in the molecule.
  • the particularly preferred amine compound is the amide-amine salt formed by reacting 1 molar portion of phthalic anhydride with 2 molar portions of di-hydrogentated tallow amine. Another preferred embodiment is the diamide formed by dehydrating this amide-amine salt.
  • amide or amine salts of monoesters of the aforesaid dicarboxylic acids are also suitable.
  • lower alkyl monoesters may also be suitable provided the nitrogen compound is an oil-soluble compound and has about 30-300 preferably 50-150 carbon atoms.
  • An octadecyl ester of an amine salt of phthalic anhydride is an example of a preferred embodiment in this category.
  • both the type of nitrogen-containing compounds and the type of ethylene vinyl acetate copolymer used have been found to be significant parameters to provide an effective two-component additive system which is a superior flow improver.
  • the flow improver combination of the present invention is a highly effective one compared with three-component systems such as disclosed in U.S. Patent 4,211,534 which are used at relatively high treatment concentrations. It has been found in the present invention that the use of a third component with its associated costs may not be necessary in many fuels.
  • the nitrogen containing compounds of the present invention are highly effective in inhibiting the growth of wax crystals.
  • the longer alkanes crystallising first generally the maximum is at around 20 to 22 carbon atoms.
  • the nitrogen containing compounds appear to be highly effective in controlling the growth of the bulk of the alkane waxes but appear to be slightly less effective in controlling the initial stages of wax precipitation.
  • the ethylene vinyl acetate copolymer contain from 10 to 40 wt.% more preferably 10 to 35 wt.%, most preferably from 10 to 20 wt.% vinyl acetate; has a number average molecular weight (M n ) as measured by Vapour Phase Osmometry within the range of about 1,000 to 30,000, preferably 1500 to 7000 more preferably 1500 to 5500 most preferably of 2500 to 5500 and a degree of branching in the range of 1 to 20 preferably 2 to 12.
  • M n number average molecular weight
  • the degree of branching is the number of methyl groups other than those of the vinyl acetate in the polymer molecule per 100 methylene groups as determined by proton nuclear magnetic resonance spectroscopy as for example using a Perkin-Elmer R-34 Spectrometer on 20% (W/W) solution in orthodichlorobenzene at 100 * C operating at 220 MHz in the continuous wave mode.
  • W e have also found that the relative proportions of the nitrogen containing compound and the ethylene vinyl acetate copolymer is important in achieving the improvement in flow and filterability.
  • at least 25 wt.% preferably at least 50 wt.% of the nitrogen containing compound should be used and more preferably between 25 and 95 wt.% preferably 50 to 95 Wt.% most preferably between 60 and 90 wt.%, especially between 60 and 80 wt.% the balance being the ethylene/vinyl acetate copolymer.
  • the additive systems of the present invention may conveniently be supplied as concentrates of the mixture of the nitrogen containing compound and the ethylene vinyl acetate copolymer in oil or other suitable inert solvent for incorporation into the bulk distillate fuel. These concentrates may also contain other additives as required. These concentrates which contain from 3 to 90 wt.% preferably from 3 to 60 wt.%, more preferably 10 to 50 wt.% of the additives in oil or other solvent are also within the scope of the present invention.
  • DOT test Flow Improved Distillate Operability Test
  • the cold flow properties of the described fuels containing the additives were determined by the slow cool flow test as follows. 300 ml of fuel are cooled linearly at I * C/hour to the test temperature then that temperature is held constant. After 2 hours at the test temperature, approximately 20 ml of the surface layer is removed by suction to prevent the test being influenced by the abnormally large wax crystals which tend to form on the oil/air interface during cooling. Wax which has settled in the bottle is dispersed by gentle stirring, then a CF PP filter assembly as described hereafter in relation to CF PP Test is inserted.
  • a vacuum of 300 mm of water is applied and 200 ml of.the fuel is passed through the filter into the graduated receiver, A PASS is recorded if the 200 ml are collected within sixty seconds through a given mesh size or a FAIL if the filter becomes blocked and the flow rate is too slow.
  • Filter assemblies with filter screens of 20, 30, 40, 60, 80, 100, 120, 150, 200, 250, 350 mesh number are used to determine the finest mesh number that a wax containing fuel will pass. The smaller are the wax crystals and therefore the finer the mesh the greater the effectiveness of the additive flow improver. It should be noted that no two fuels will give exactly the same test results at the same treatment level for the same flow improver additive, and, therefore, actual treat levels will vary somewhat from fuel to fuel.
  • Fuel 1 was evaluated in the DOT test using a flow improver composed of 75% by weight of Nitrogen Compound A, and 25% by weight of EVA Polymer 1 and the results at -12°C are reported below:
  • Example 1 -' was conducted with the conventional flow improver additive as reported in Example 1, polymer 1 in U.S. Patent 4,211,534.
  • This flow improver additive is described as a polymer mixture of about 75 wt.% of a wax growth arrestor and about 25 wt.% of a nucleator, both compounds being ethylene vinyl acetate polymer, henceforth referred to as Polymer 15.
  • Example 1 The DOT test used in Example 1 was repeated using Fuel 3. All tests were at -12 * C with 100 ppm flow improver composed of 75 ppm Nitrogen Compound A of Example 1 and 25 ppm of various ethylene vinyl acetate copolymers (EVA) tabulated below. Results are in Table 1. The purpose of this example is to demonstrate the importance of the particular category of ethylene-vinyl acetate copolymers.
  • Example 6 The comparison of Example 6 was repeated in Fuels 2 and 3 and the results are shown in Figures 2 and 3 respectively.
  • Example 9 was repeated but using Fuels 2 and 3 and the results are shown in Figures 5 and 6 respectively.
  • a 40 ml sample of the oil to be tested is cooled in a bath which is maintained at about -34°C to give non-linear cooling at about 1'C/min.
  • a test device which is a pipette to whose lower end is attached an inverted funnel which is positioned below the surface of the oil to be tested. Stretched across the mouth of the funnel is a 350 mesh screen having an area defined by a 12 millimetre diameter.
  • the periodic tests are each initiated by applying a vacuum to the upper end of the pipette whereby oil is drawn through the screen up into the pipette to a mark indicating 20 ml of oil. After each successful passage the oil is returned immediately to the CFPP tube. The test is repeated with each one degree drop in temperature until the oil fails to fill the pipette within 60 seconds. This temperature is reported as the CFPP temperature. The difference between the CF PP of an additive free fuel and of the same fuel containing additive is reported as the CFPP depression by the additive. A more effective additive flow improver gives a greater CF P P depression at the same concentration of additive.
  • Example 12 The evaluations of Example 12 were repeated in Fuels 2 and 3 and the results are recorded in Figures 8 and 9 respectively.
  • Example 15 was repeated but using Fuels 2 and 3 and the results are recorded in Figures 11 and 12 respectively.
  • the performance of the additives is evaluated in a test developed for the low temperature properties of diesel fuels in which a sample of the fuel is brought to the test temperature by cooling at 2'F per hour and testing the filterability at that temperature by determining if the fuel will pass through a 350 mesh screen under a vacuum of 6 inches of mercury within 60 seconds. If so the fuel is considered to PASS.
  • the ethylene vinyl acetate copolymers used in this Example had the following structure Mixtures of Nitrogen Compound A with varying amounts of ethylene vinyl acetate copolymers 9 to 14 were tested in Fuels 4 and 5, the amount of additive needed to PASS the test being recorded in Figures 13 and 14 respectively. The lower the amount of additive showing the better performance of the additive.
  • the fuel in one barrel contained 135 parts per million of Polymer 15 and only passed a 30 mesh screen whilst the fuel in the other barrel which contained 135 parts per million of a mixture of 4 parts of Nitrogen Compound A and 1 part of EVA Polymer 1 passed a 100 mesh screen.
  • the results are from four 25 m 3 tanks of Fuel 7 which were tested side by side. Over a period of three weeks storage, under natural cold conditions (including natural temperature cycling), the fuel at -14°C was pumped out of the tanks as in a fuel distribution situation - and the finest filter screen that the fuel would flow through was recorded as follows

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP82301556A 1981-03-31 1982-03-24 Additif à deux composants pour améliorer l'écoulement des huiles combustibles distillats moyens Expired EP0061894B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82301556T ATE15496T1 (de) 1981-03-31 1982-03-24 Zwei-komponentenzusatz zur verbesserung der fliessfaehigkeit von mittleren destillat-heizoelen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8110082 1981-03-31
GB8110082 1981-03-31

Publications (3)

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EP0061894A2 true EP0061894A2 (fr) 1982-10-06
EP0061894A3 EP0061894A3 (en) 1983-01-19
EP0061894B1 EP0061894B1 (fr) 1985-09-11

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EP82301556A Expired EP0061894B1 (fr) 1981-03-31 1982-03-24 Additif à deux composants pour améliorer l'écoulement des huiles combustibles distillats moyens

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EP (1) EP0061894B1 (fr)
JP (2) JPS581792A (fr)
AT (1) ATE15496T1 (fr)
AU (1) AU547501B2 (fr)
BG (1) BG60057B2 (fr)
CA (1) CA1182641A (fr)
CS (1) CS275637B6 (fr)
DD (1) DD208170A5 (fr)
DE (1) DE3266117D1 (fr)
GB (1) GB2095698A (fr)
HU (1) HU199552B (fr)
IN (1) IN158487B (fr)
MX (2) MX172089B (fr)
PL (1) PL129941B1 (fr)
RU (1) RU2017794C1 (fr)
SG (1) SG58888G (fr)
YU (1) YU45106B (fr)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0104015A2 (fr) * 1982-09-16 1984-03-28 Exxon Research And Engineering Company Concentrés d'additif pour combustibles distillés
EP0113581A1 (fr) * 1983-01-04 1984-07-18 Exxon Research And Engineering Company Compositions distillées intermédiaires avec propriété d'écoulement à basse température améloirée
EP0153176A2 (fr) * 1984-02-21 1985-08-28 Exxon Research And Engineering Company Compositions de distillat moyen à caractéristiques d'écoulement à froid
EP0155807A2 (fr) * 1984-03-22 1985-09-25 Exxon Research And Engineering Company Compositions de distillat moyen avec des caractéristiques d'écoulement à froid
US4569679A (en) * 1984-03-12 1986-02-11 Exxon Research & Engineering Co. Additive concentrates for distillate fuels
EP0203812A1 (fr) * 1985-05-28 1986-12-03 Exxon Research And Engineering Company Composition pour l'écoulement des combustibles à base de distillats moyens
EP0217602A1 (fr) * 1985-09-24 1987-04-08 Mitsubishi Petrochemical Co., Ltd. Additif pour huile combustible et huile combustible ayant une fluidité modifiée
EP0261958A2 (fr) * 1986-09-24 1988-03-30 Exxon Chemical Patents Inc. Compositions de distillat moyen avec des cristaux de cire de taille réduite
EP0261959A2 (fr) * 1986-09-24 1988-03-30 Exxon Chemical Patents Inc. Additifs pour mazout
WO1988002393A2 (fr) * 1986-09-24 1988-04-07 Exxon Chemical Patents, Inc. Additifs pour carburant
GB2208517B (en) * 1986-09-24 1990-10-03 Exxon Chemical Patents Inc Middle distillate compositions with reduced wax crystal size
GB2231584A (en) * 1986-09-24 1990-11-21 Exxon Chemical Patents Inc Improved fuel additives
AT394569B (de) * 1986-09-24 1992-05-11 Exxon Chemical Patents Inc Mitteldestillatzusammensetzungen mit verminderter wachskristallgroesse
WO1993014178A1 (fr) * 1992-01-14 1993-07-22 Exxon Chemical Patents Inc. Additifs et compositions du type combustible
EP0857776A1 (fr) 1997-01-07 1998-08-12 Clariant GmbH Amélioration de la fluidité d'huiles minérales et de distillates d'huiles minérales par l'utilisation de résines alkylphénol-aldéhyde
US5814110A (en) * 1986-09-24 1998-09-29 Exxon Chemical Patents Inc. Chemical compositions and use as fuel additives
US6010989A (en) * 1997-09-08 2000-01-04 Clariant Gmbh Additive for improving the flow properties of mineral oils and mineral oil distillates
US7041738B2 (en) 2002-07-09 2006-05-09 Clariant Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
GB2435884A (en) * 2006-03-09 2007-09-12 Infineum Int Ltd Ethylene/vinyl ester and phenolic resin fuel additive package
US7435271B2 (en) 2000-01-11 2008-10-14 Clariant Produkte (Deutschland) Gmbh Multifunctional additive for fuel oils
US7550019B2 (en) 2003-07-21 2009-06-23 Clariant Produkte (Deutschland) Gmbh Fuel oil additives and additized fuel oils having improved cold properties
US7713315B2 (en) 2005-07-28 2010-05-11 Clariant Produkte (Deutschland) Gmbh Mineral oils with improved conductivity and cold flowability
EP2230226A1 (fr) * 2009-03-18 2010-09-22 Infineum International Limited Additifs pour huiles de carburant
US7815696B2 (en) 2002-07-09 2010-10-19 Clariant Produkte (Deutschland) Gmbh Oxidation-stabilized lubricant additives for highly desulfurized fuel oils
US8133852B2 (en) 2005-07-28 2012-03-13 Clariant Produkte (Deutschland) Gmbh Mineral oils with improved conductivity and cold flowability
US8283298B2 (en) 2005-07-28 2012-10-09 Clariant Produkte (Deutschland) Gmbh Mineral oils with improved conductivity and cold flowability
US8298402B2 (en) 2005-09-22 2012-10-30 Clariant Produkte (Deutschland) Gmbh Additives for improving the cold flowability and lubricity of fuel oils
EP3885424A1 (fr) 2020-03-24 2021-09-29 Clariant International Ltd Compositions et procédés de dispersion des paraffines dans des huiles de combustible à faible teneur en soufre

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60166389A (ja) * 1984-02-09 1985-08-29 Nippon Oil & Fats Co Ltd 燃料油用流動性向上剤
GB8510719D0 (en) * 1985-04-26 1985-06-05 Exxon Chemical Patents Inc Fuel compositions
GB2197878A (en) * 1986-10-07 1988-06-02 Exxon Chemical Patents Inc Middle distillate compositions with reduced wax crystal size
GB2197877A (en) * 1986-10-07 1988-06-02 Exxon Chemical Patents Inc Additives for wax containing distillated fuel
DE4237662A1 (de) * 1992-11-07 1994-05-11 Basf Ag Erdölmitteldestillatzusammensetzungen
GB9818210D0 (en) * 1998-08-20 1998-10-14 Exxon Chemical Patents Inc Oil additives and compositions
DE102004014080A1 (de) * 2004-03-23 2005-10-13 Peter Dr. Wilharm Nukleierungsmittel auf der Basis von hyperverzweigten Polymeren
GB0902009D0 (en) * 2009-02-09 2009-03-11 Innospec Ltd Improvements in fuels

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3850587A (en) * 1973-11-29 1974-11-26 Chevron Res Low-temperature flow improves in fuels
US3961916A (en) * 1972-02-08 1976-06-08 Exxon Research And Engineering Company Middle distillate compositions with improved filterability and process therefor
FR2300792A1 (fr) * 1975-02-13 1976-09-10 Exxon Research Engineering Co Composition de fuel-oil comportant un agent azote d'amelioration de l'ecoulement a froid
FR2384014A1 (fr) * 1977-03-16 1978-10-13 Exxon Research Engineering Co Combinaisons de copolymeres aliphatiques avec des derives azotes d'acides succiniques substitues et leur utilisation comme agents d'amelioration de l'ecoulement des huiles combustibles
FR2426730A1 (fr) * 1978-05-25 1979-12-21 Exxon Research Engineering Co Compositions d'additifs pour ameliorer l'ecoulement et la filtrabilite des fuel-oils distilles

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE858666A (fr) * 1977-09-13 1978-03-13 Exxon Research Engineering Co Combinaisons de polymeres convenant dans des huiles d'hydrocarbures pour ameliorer les proprietes d'ecoulement aux basses temperatures

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3961916A (en) * 1972-02-08 1976-06-08 Exxon Research And Engineering Company Middle distillate compositions with improved filterability and process therefor
US3850587A (en) * 1973-11-29 1974-11-26 Chevron Res Low-temperature flow improves in fuels
FR2300792A1 (fr) * 1975-02-13 1976-09-10 Exxon Research Engineering Co Composition de fuel-oil comportant un agent azote d'amelioration de l'ecoulement a froid
FR2384014A1 (fr) * 1977-03-16 1978-10-13 Exxon Research Engineering Co Combinaisons de copolymeres aliphatiques avec des derives azotes d'acides succiniques substitues et leur utilisation comme agents d'amelioration de l'ecoulement des huiles combustibles
FR2426730A1 (fr) * 1978-05-25 1979-12-21 Exxon Research Engineering Co Compositions d'additifs pour ameliorer l'ecoulement et la filtrabilite des fuel-oils distilles

Cited By (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0104015A2 (fr) * 1982-09-16 1984-03-28 Exxon Research And Engineering Company Concentrés d'additif pour combustibles distillés
EP0104015A3 (en) * 1982-09-16 1984-06-27 Exxon Research And Engineering Company Improved additive concentrates for distillate fuels
US4537602A (en) * 1982-09-16 1985-08-27 Exxon Research & Engineering Co. Additive concentrates for distillate fuels
EP0113581A1 (fr) * 1983-01-04 1984-07-18 Exxon Research And Engineering Company Compositions distillées intermédiaires avec propriété d'écoulement à basse température améloirée
EP0153176A3 (en) * 1984-02-21 1985-11-27 Exxon Research And Engineering Company Middle distillate compositions with improved cold flow properties
EP0153177A2 (fr) * 1984-02-21 1985-08-28 Exxon Research And Engineering Company Compositions de distillat moyen à caractéristiques d'écoulement à froid
EP0153177A3 (en) * 1984-02-21 1985-12-04 Exxon Research And Engineering Company Middle distillate compositions with improved low temperature properties
EP0153176A2 (fr) * 1984-02-21 1985-08-28 Exxon Research And Engineering Company Compositions de distillat moyen à caractéristiques d'écoulement à froid
US4569679A (en) * 1984-03-12 1986-02-11 Exxon Research & Engineering Co. Additive concentrates for distillate fuels
EP0155807A2 (fr) * 1984-03-22 1985-09-25 Exxon Research And Engineering Company Compositions de distillat moyen avec des caractéristiques d'écoulement à froid
EP0156577A2 (fr) * 1984-03-22 1985-10-02 Exxon Research And Engineering Company Compositions de distillat moyen avec des caractéristiques d'écoulement à froid
EP0155807A3 (fr) * 1984-03-22 1985-11-27 Exxon Research And Engineering Company Compositions de distillat moyen avec des caractéristiques d'écoulement à froid
EP0156577A3 (en) * 1984-03-22 1985-12-04 Exxon Research And Engineering Company Middle distillate compositions with improved cold flow properties
EP0203812A1 (fr) * 1985-05-28 1986-12-03 Exxon Research And Engineering Company Composition pour l'écoulement des combustibles à base de distillats moyens
US4802892A (en) * 1985-09-24 1989-02-07 Mitsubishi Petrochemical Co., Ltd. Fuel oil additive and fuel oil having improved flowability
EP0217602A1 (fr) * 1985-09-24 1987-04-08 Mitsubishi Petrochemical Co., Ltd. Additif pour huile combustible et huile combustible ayant une fluidité modifiée
GB2208517B (en) * 1986-09-24 1990-10-03 Exxon Chemical Patents Inc Middle distillate compositions with reduced wax crystal size
GB2231584A (en) * 1986-09-24 1990-11-21 Exxon Chemical Patents Inc Improved fuel additives
WO1988002393A2 (fr) * 1986-09-24 1988-04-07 Exxon Chemical Patents, Inc. Additifs pour carburant
US5814110A (en) * 1986-09-24 1998-09-29 Exxon Chemical Patents Inc. Chemical compositions and use as fuel additives
AT394569B (de) * 1986-09-24 1992-05-11 Exxon Chemical Patents Inc Mitteldestillatzusammensetzungen mit verminderter wachskristallgroesse
EP0261958A3 (fr) * 1986-09-24 1988-06-15 Exxon Chemical Patents Inc. Compositions de distillat moyen avec des cristaux de cire de taille réduite
EP0261959A3 (en) * 1986-09-24 1988-06-29 Exxon Chemical Patents Inc. Improved fuel additives
EP0261959A2 (fr) * 1986-09-24 1988-03-30 Exxon Chemical Patents Inc. Additifs pour mazout
EP0261958A2 (fr) * 1986-09-24 1988-03-30 Exxon Chemical Patents Inc. Compositions de distillat moyen avec des cristaux de cire de taille réduite
WO1988002394A2 (fr) * 1986-09-24 1988-04-07 Exxon Chemical Patents, Inc. Compositions distillees moyennes avec grandeur reduite des cristaux de paraffine
GB2231584B (en) * 1986-09-24 1991-03-06 Exxon Chemical Patents Inc Improved fuel additives
AT394568B (de) * 1986-09-24 1992-05-11 Exxon Chemical Patents Inc Verbesserte brennstoffadditive
WO1988002393A3 (fr) * 1986-10-07 1988-05-05 Exxon Chemical Patents Inc Additifs pour carburant
WO1988002394A3 (fr) * 1986-10-07 1988-05-05 Exxon Chemical Patents Inc Compositions distillees moyennes avec grandeur reduite des cristaux de paraffine
WO1993014178A1 (fr) * 1992-01-14 1993-07-22 Exxon Chemical Patents Inc. Additifs et compositions du type combustible
EP0857776A1 (fr) 1997-01-07 1998-08-12 Clariant GmbH Amélioration de la fluidité d'huiles minérales et de distillates d'huiles minérales par l'utilisation de résines alkylphénol-aldéhyde
US5998530A (en) * 1997-01-07 1999-12-07 Clariant Gmbh Flowability of mineral oils and mineral oil distillates using alkylphenol-aldehyde resins
US6010989A (en) * 1997-09-08 2000-01-04 Clariant Gmbh Additive for improving the flow properties of mineral oils and mineral oil distillates
US7435271B2 (en) 2000-01-11 2008-10-14 Clariant Produkte (Deutschland) Gmbh Multifunctional additive for fuel oils
US7041738B2 (en) 2002-07-09 2006-05-09 Clariant Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
US7815696B2 (en) 2002-07-09 2010-10-19 Clariant Produkte (Deutschland) Gmbh Oxidation-stabilized lubricant additives for highly desulfurized fuel oils
US7550019B2 (en) 2003-07-21 2009-06-23 Clariant Produkte (Deutschland) Gmbh Fuel oil additives and additized fuel oils having improved cold properties
US7713315B2 (en) 2005-07-28 2010-05-11 Clariant Produkte (Deutschland) Gmbh Mineral oils with improved conductivity and cold flowability
US8133852B2 (en) 2005-07-28 2012-03-13 Clariant Produkte (Deutschland) Gmbh Mineral oils with improved conductivity and cold flowability
US8283298B2 (en) 2005-07-28 2012-10-09 Clariant Produkte (Deutschland) Gmbh Mineral oils with improved conductivity and cold flowability
US8298402B2 (en) 2005-09-22 2012-10-30 Clariant Produkte (Deutschland) Gmbh Additives for improving the cold flowability and lubricity of fuel oils
GB2435884A (en) * 2006-03-09 2007-09-12 Infineum Int Ltd Ethylene/vinyl ester and phenolic resin fuel additive package
EP2230226A1 (fr) * 2009-03-18 2010-09-22 Infineum International Limited Additifs pour huiles de carburant
US10308593B2 (en) 2009-03-18 2019-06-04 Infineum International Limited Additives for fuel oils
EP3885424A1 (fr) 2020-03-24 2021-09-29 Clariant International Ltd Compositions et procédés de dispersion des paraffines dans des huiles de combustible à faible teneur en soufre
WO2021190793A1 (fr) 2020-03-24 2021-09-30 Clariant International Ltd Compositions et procédés de dispersion de paraffines dans des huiles combustibles à faible teneur en soufre
WO2021190794A1 (fr) 2020-03-24 2021-09-30 Clariant International Ltd Compositions et procédés de dispersion de paraffines dans des huiles combustibles à faible teneur en soufre
US11993756B2 (en) 2020-03-24 2024-05-28 Clariant International Ltd Compositions and methods of dispergating paraffins in sulphur-low fuel oils

Also Published As

Publication number Publication date
JPH02289686A (ja) 1990-11-29
PL129941B1 (en) 1984-06-30
AU8218382A (en) 1982-10-07
CS8202251A2 (en) 1991-04-11
CS275637B6 (en) 1992-03-18
YU45106B (en) 1992-03-10
JPH0353355B2 (fr) 1991-08-14
PL235709A1 (fr) 1982-10-25
DD208170A5 (de) 1984-03-28
IN158487B (fr) 1986-11-22
GB2095698A (en) 1982-10-06
CA1182641A (fr) 1985-02-19
JPS581792A (ja) 1983-01-07
MX160804A (es) 1990-05-25
ATE15496T1 (de) 1985-09-15
AU547501B2 (en) 1985-10-24
EP0061894B1 (fr) 1985-09-11
SG58888G (en) 1989-03-10
BG60057B2 (bg) 1993-08-30
RU2017794C1 (ru) 1994-08-15
YU70082A (en) 1985-03-20
EP0061894A3 (en) 1983-01-19
JPH0258318B2 (fr) 1990-12-07
HU199552B (en) 1990-02-28
MX172089B (es) 1993-12-02
DE3266117D1 (en) 1985-10-17

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