EP0061894B1 - 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
EP0061894B1
EP0061894B1 EP82301556A EP82301556A EP0061894B1 EP 0061894 B1 EP0061894 B1 EP 0061894B1 EP 82301556 A EP82301556 A EP 82301556A EP 82301556 A EP82301556 A EP 82301556A EP 0061894 B1 EP0061894 B1 EP 0061894B1
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EP
European Patent Office
Prior art keywords
process according
flow
vinyl acetate
nitrogen compound
oil
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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.)
Expired
Application number
EP82301556A
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German (de)
English (en)
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EP0061894A2 (fr
EP0061894A3 (en
Inventor
Robert Dryden Tack
Brian William Davies
Kenneth Lewtas
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Priority to AT82301556T priority Critical patent/ATE15496T1/de
Publication of EP0061894A2 publication Critical patent/EP0061894A2/fr
Publication of EP0061894A3 publication Critical patent/EP0061894A3/en
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    • 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 IInyckyj 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 llynckyj 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 30-300 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.
  • improved 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 two component 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 120°C to 500°C (ASTM D1160), preferably those distillate fuels boiling in the range of 150°C-400°C.
  • the invention is especially applicable to fuels which have a relatively high final boiling point (FBP), 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 I 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 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-hydrogenated 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 provided the nitrogen compound is an oil-soluble compound and has 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 contains from 10 to 40 wt.% preferably 10 to 35 wt.%, more 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 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.
  • 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 1°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 CFPP filter assembly as described hereafter in relation to CFPP 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 repeated but using Fuel 2 with the following results:
  • Example 1 For the purpose of comparison, the test of 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. * Branching is the number of methyls per 100 methylene groups excluding the vinyl acetate methyls as measured by'H NMR Nuclear Magnetic Resonance spectroscopy. All spectra were run on a Perkin-Elmer R-34 spectrometer on 20% (w/w) solution in orthodichlorobenzene at 100°C operating at 220 MHz.
  • 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.
  • Periodically at each one degree Centigrade drop in temperature starting from at least 2°C above the cloud point, the cooled oil is tested for its ability to flow through a fine screen in a prescribed time period using 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 CFPP 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 CFPP 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.
  • 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 fitter 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)

Claims (20)

1. Procédé pour améliorer les propriétés d'écoulement à basse température d'une huile combustible du type d'un distillat moyen contenant une cire, bouillant dans l'intervalle de 120 à 500°C, consistant à incorporer à cette huile 0,005 à 0,5 % en poids, de préférence 0,005 à 0,25 % en poids d'un agent à deux composants améliorant l'écoulement et l'aptitude à la filtration, comprenant essentiellement:
comme premier composant
(a) 25 à 95 % en poids, sur la base d'un poids total d'agent améliorant l'écoulement, d'un composé azoté soluble dans l'huile en C30 à C300 inhibant la croissance des cristaux de cire, portant au moins une chaîne alkylique droite en Cs à C40 et étant choisi dans la classe comprenant des sels d'alkylammonium et/ou des amides d'acides polycarboxyliques aromatiques ou cycloaliphatiques ou de leurs anhydrides ou des sels d'amide/amine de mono-esters desdits acides polycarboxyliques, et
comme second composant
(b) 75 à 5 % en poids d'un copolymère éthylène-acétate de vinyle ayant une teneur en acétate de vinyle de 10 à 40 % en poids et une moyenne en nombre (Mn) du poids moléculaire de 1000 à 30 000 et un degré de ramification dans l'intervalle de 1 à 20 groupes méthyle par 100 groupes méthylène comme déterminé par spectroscopie de résonance magnétique nucléaire (RMN 'H).
2. Procédé suivant la revendication 1, dans lequel l'agent améliorant l'écoulement et l'aptitude à la filtration est essentiellement formé de 50 à 90 % en poids de (a) et de 50 à 10 % en poids de (b).
3. Procédé suivant la revendication 1 ou la revendication 2, dans lequel le composé azoté soluble dans l'huile contient 50 à 150 atomes de carbone.
4. Procédé suivant l'une quelconque des revendications précédentes, dans lequel le composé azoté soluble dans l'huile contient au moins trois chaînes alkyliques renfermant 8 à 40 atomes de carbone.
5. Procédé suivant l'une quelconque des revendications précédentes, dans lequel le composé azoté soluble dans l'huile est obtenu en faisant réagir une amine secondaire de suif hydrogéné avec un acide polycarboxylique aromatique ou cycloaliphatique ou son anhydride.
6. Procédé suivant la revendication 5, dans lequel l'acide polycarboxylique aromatique est l'acide phtalique ou son anhydride.
7. Procédé suivant la revendication 5 ou la revendication 6, dans lequel le composé azoté soluble dans l'huile est le sel d'amide-amine formé en faisant réagir une proportion molaire d'anhydride phtalique et 2 proportions molaires de di-(suif hydrogéné)-amine.
8. Procédé suivant l'une quelconque des revendications précédentes, dans lequel l'agent améliorant l'écoulement et l'aptitude à la filtration contient 60 à 80 % en poids du composé azoté soluble dans l'huile.
9. Procédé suivant la revendication 1 ou la revendication 2, dans lequel le copolymère d'éthylène et d'acétate de vinyle contient 10 à 20 % en poids d'acétate de vinyle.
10. Procédé suivant la revendication 1 ou la revendication 2, dans lequel le composé azoté soluble dans l'huile contient 50 à 150 atomes de carbone.
11. Procédé suivant l'une quelconque des revendications précédentes, dans lequel l'agent améliorant l'écoulement et l'aptitude à la filtration est incorporé à l'huile combustible du type d'un distillat moyen par addition à cette huile de la quantité appropriée d'une solution dans un solvant inerte contenant 3 à 60 % en poids d'un mélange de deux composants améliorant l'écoulement et l'aptitude à la filtration, comprenant essentiellement:
comme premier composant
(a) 25 à 95 % en poids, sur la base d'un poids total d'agent améliorant l'écoulement, d'un composé azoté soluble dans l'huile en C30 à C300 inhibant la croissance des cristaux de cire, portant au moins une chaîne alkylique droite en Cs à C40 et étant choisi dans la classe comprenant des sels d'alkylammonium et/ou des amides d'acides polycarboxyliques aromatiques ou cycloaliphatiques ou de leurs anhydrides ou des sels d'amide/amine de monoesters desdits acides polycarboxyliques, et
comme second composant
(b) 75 à 5 % en poids d'un copolymère éthylène-acétate de vinyle ayant une teneur en acétate de vinyle de 10 à 40 % en poids et une moyenne en nombre (Mn) du poids moléculaire de 1000 à 30 000 et un degré de ramification dans l'intervalle de 1 à 20 groupes méthyle par 100 groupes méthylène comme déterminé par spectroscopie de résonance magnétique nucléaire (RMN 1H).
12. Procédé suivant la revendication 11, dans lequel la solution contient 10 à 50 % en poids du mélange améliorant l'écoulement et l'aptitude à la filtration.
13. Procédé suivant la revendication 11 ou la revendication 12, dans lequel la solution contient 50 à 90 % en poids de (a) et 50 à 10 % en poids de (b).
14. Procédé suivant l'une quelconque des revendications 11 à 13, dans lequel le copolymère d'éthylène et d'acétate de vinyle a un degré de ramification de 2 à 12.
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 EP0061894A2 (fr) 1982-10-06
EP0061894A3 EP0061894A3 (en) 1983-01-19
EP0061894B1 true EP0061894B1 (fr) 1985-09-11

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EP (1) EP0061894B1 (fr)
JP (2) JPS581792A (fr)
AT (1) ATE15496T1 (fr)
AU (1) AU547501B2 (fr)
BG (1) BG60057A3 (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) MX160804A (fr)
PL (1) PL129941B1 (fr)
RU (1) RU2017794C1 (fr)
SG (1) SG58888G (fr)
YU (1) YU45106B (fr)

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DE102004014080A1 (de) * 2004-03-23 2005-10-13 Peter Dr. Wilharm Nukleierungsmittel auf der Basis von hyperverzweigten Polymeren
US11993756B2 (en) 2020-03-24 2024-05-28 Clariant International Ltd Compositions and methods of dispergating paraffins in sulphur-low fuel oils

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US4569679A (en) * 1984-03-12 1986-02-11 Exxon Research & Engineering Co. Additive concentrates for distillate fuels
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EP0261958A3 (fr) * 1986-09-24 1988-06-15 Exxon Chemical Patents Inc. Compositions de distillat moyen avec des cristaux de cire de taille réduite
EP0261959B1 (fr) * 1986-09-24 1995-07-12 Exxon Chemical Patents Inc. Additifs pour mazout
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GB2197877A (en) * 1986-10-07 1988-06-02 Exxon Chemical Patents Inc Additives for wax containing distillated fuel
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DE4237662A1 (de) * 1992-11-07 1994-05-11 Basf Ag Erdölmitteldestillatzusammensetzungen
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EP1116780B1 (fr) 2000-01-11 2005-08-31 Clariant GmbH Additif polyfonctionnel pour huiles combustibles
DE50307929D1 (de) 2002-07-09 2007-09-27 Clariant Produkte Deutschland Oxidationsstabilisierte Schmieradditive für hochentschwefelte Brennstofföle
CA2431746C (fr) 2002-07-09 2011-11-01 Clariant Gmbh Ameliorant de l'ecoulement a froid pour des huiles combustibles d'origine vegetale ou animale
DE10333043A1 (de) 2003-07-21 2005-03-10 Clariant Gmbh Brennstofföladditive und additivierte Brennstofföle mit verbesserten Kälteeigenschaften
DE102005035276B4 (de) 2005-07-28 2007-10-11 Clariant Produkte (Deutschland) Gmbh Mineralöle mit verbesserter Leitfähigkeit und Kältefließfähigkeit
DE102005035275B4 (de) 2005-07-28 2007-10-11 Clariant Produkte (Deutschland) Gmbh Mineralöle mit verbesserter Leitfähigkeit und Kältefließfähigkeit
DE102005035277B4 (de) 2005-07-28 2007-10-11 Clariant Produkte (Deutschland) Gmbh Mineralöle mit verbesserter Leitfähigkeit und Kältefließfähigkeit
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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

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PL129941B1 (en) 1984-06-30
GB2095698A (en) 1982-10-06
YU70082A (en) 1985-03-20
BG60057A3 (en) 1993-08-16
JPH02289686A (ja) 1990-11-29
JPS581792A (ja) 1983-01-07
JPH0258318B2 (fr) 1990-12-07
PL235709A1 (fr) 1982-10-25
DE3266117D1 (en) 1985-10-17
AU8218382A (en) 1982-10-07
RU2017794C1 (ru) 1994-08-15
HU199552B (en) 1990-02-28
JPH0353355B2 (fr) 1991-08-14
EP0061894A2 (fr) 1982-10-06
CS275637B6 (en) 1992-03-18
SG58888G (en) 1989-03-10
CA1182641A (fr) 1985-02-19
AU547501B2 (en) 1985-10-24
ATE15496T1 (de) 1985-09-15
DD208170A5 (de) 1984-03-28
IN158487B (fr) 1986-11-22
EP0061894A3 (en) 1983-01-19
MX160804A (es) 1990-05-25
CS8202251A2 (en) 1991-04-11
YU45106B (en) 1992-03-10
MX172089B (es) 1993-12-02

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