EP0254284B1 - Procédé pour améliorer la fluidité d'huiles minérales et de distillats d'huile minérales - Google Patents
Procédé pour améliorer la fluidité d'huiles minérales et de distillats d'huile minérales Download PDFInfo
- Publication number
- EP0254284B1 EP0254284B1 EP87110581A EP87110581A EP0254284B1 EP 0254284 B1 EP0254284 B1 EP 0254284B1 EP 87110581 A EP87110581 A EP 87110581A EP 87110581 A EP87110581 A EP 87110581A EP 0254284 B1 EP0254284 B1 EP 0254284B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- vinyl acetate
- ethylene
- weight
- parts
- mineral oil
- 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.)
- Expired - Lifetime
Links
- 239000002480 mineral oil Substances 0.000 title claims description 40
- 235000010446 mineral oil Nutrition 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 11
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 29
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 229920001897 terpolymer Polymers 0.000 claims abstract description 20
- 239000005977 Ethylene Substances 0.000 claims abstract description 19
- 229920001577 copolymer Polymers 0.000 claims abstract description 13
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 19
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 238000000214 vapour pressure osmometry Methods 0.000 claims description 6
- 230000001747 exhibiting effect Effects 0.000 claims 2
- 229920000642 polymer Polymers 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 239000010779 crude oil Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- GFJUOMJGSXRJJY-UHFFFAOYSA-N 2-methylprop-1-ene Chemical compound CC(C)=C.CC(C)=C GFJUOMJGSXRJJY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RBWPSNAYKUWOCG-UHFFFAOYSA-N CC(C)=C.CC(C)=C.C(C)(=O)OC=C.C=C Chemical group CC(C)=C.CC(C)=C.C(C)(=O)OC=C.C=C RBWPSNAYKUWOCG-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000010763 heavy fuel oil Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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
- 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
Definitions
- the present invention relates to a process for improving the flowability of mineral oils and mineral oil distillates by adding mixtures of an ethylene-vinyl acetate-diisobutylene terpolymer and an ethylene-vinyl acetate copolymer.
- Mineral oils such as crude oil, diesel fuel or heating oil contain dissolved paraffin, which crystallizes out at low temperatures. These solid deposits often lead to disruptions in the extraction and use of mineral oils. For example, the ability of crude oil production and transport facilities to function until their complete failure are impaired. In diesel engines and combustion plants, the filters can become clogged, which ultimately results in an interruption in the fuel or heating medium supply.
- additives are added to mineral oils that counteract the formation of wax crystals. This prevents an increase in the viscosity of the oils and lowers their pour point.
- Copolymers of ethylene and carboxylic acid esters of vinyl alcohol have become very important as pour point depressants and flow improvers for crude oils and middle distillates.
- ethylene-vinyl acetate copolymers have proven particularly useful.
- Such copolymers and their use are described, for example, in DE-PS 19 14 756. They are generally manufactured by copolymerization of the monomers in autoclaves at temperatures from 80 to 150 ° C and pressures from 5 to 15 MPa in the presence of peroxides as initiators and organic solvents as the reaction medium.
- the remedy is to add large quantities or to mix the mineral oil or mineral oil distillate with low-boiling hydrocarbons.
- DE 26 39 672 Al describes mixtures of polymers with an ethylene skeleton and copolymers of C2bis C50 olefins, which can lead to a synergistic improvement in the flow properties of distillate hydrocarbon oils in the cold.
- the object was therefore to find additives which have an even greater range of uses than the known flow improvers. They are also intended to increase the flowability of oils in which the known additives have little or no effect.
- the object described above is achieved by a method for improving the flowability of mineral oils and mineral oil distillates. It is characterized in that mixtures of an ethylene-vinyl acetate-diisobutylene terpolymer and an ethylene-vinyl acetate copolymer are added to the mineral oils or mineral oil distillates.
- the ethylene-vinyl acetate-diisobutylene terpolymers used according to the invention contain 25 to 78 parts by weight of vinyl acetate and 0.5 to 45 parts by weight of diisobutylene per 100 parts by weight of ethylene. Terpolymers with 30 to 55 parts by weight of vinyl acetate and 1.0 to 27.5 parts by weight of diisobutylene per 100 parts by weight of ethylene have proven particularly useful.
- the average molecular weight of the terpolymers measured by vapor pressure osmometry is 500 to 10 000 g.mol -1 , preferably 1000 to 5000.g mol -1 and in particular 1500 to 3500.g mol -1 .
- Each 100 CH2 groups have 6 to 20 and preferably 7 to 15 CH3 groups in the side chains, which do not result from the acetate residue of the vinyl acetate.
- the number of CH3 groups is determined by H-NMR spectroscopy.
- the production of the ethylene-vinyl acetate-diisobutylene terpolymers is known. It can e.g. by polymerization of the monomer mixture at pressures above 50 MPa and temperatures from 150 to 350 ° C. in the presence of oxygen or radical initiators in autoclaves or tubular reactors.
- Diisobutylene is a mixture consisting essentially of 2,4,4-trimethylpentene (1) and 2,4,4-trimethylpentene (2). It is formed during the dimerization of isobutylene (2-methylpropene) with acidic catalysts (e.g. ion exchangers).
- acidic catalysts e.g. ion exchangers
- the ethylene-vinyl acetate copolymers used according to the invention contain 5 to 54 parts by weight of vinyl acetate per 100 parts by weight of ethylene. Copolymers with 11 to 33 parts by weight of vinyl acetate per 100 parts by weight of ethylene have proven particularly useful.
- the average molecular weight of the copolymers which, like the average molecular weight of the terpolymers, is measured by vapor pressure osmometry, is 500 to 10 000 g.mo l-1 .
- Copolymers with a molecular weight of 1,000 to 5,000 g.mol -1 have proven particularly useful.
- Each l00 CH2 groups have the copolymers l to l0 and preferably 3 to 7 CH3 groups in the side chains, which do not result from the acetate residue of the vinyl acetate.
- the number of CH3 groups is determined by H-NMR spectroscopy.
- the production of the ethylene-vinyl acetate copolymers is known. It can e.g. by polymerization of the monomer mixture at pressures of 5 to 15 MPa and temperatures of 70 to 150 ° C in the presence of free radical initiators.
- An organic solvent or suspension medium such as toluene can be used as the reaction medium.
- the weight ratio of ethylene-vinyl acetate-diisobutylene terpolymer and ethylene-vinyl acetate copolymer in the mixtures is 100: 1 to 1: 1. Mixtures containing the terpolymer and copolymer in a weight ratio of 20: 1 to 3: 1 are preferred.
- the process according to the invention improves both the flowability of mineral oils and of mineral oil distillates.
- mineral oils is understood to mean crude oils and distillation residues such as heavy fuel oil.
- Mineral oil distillates are hydrocarbon fractions with a boiling temperature between about 150 and 400 ° C. These include, for example, petroleum, light heating oils and diesel fuel. Middle distillates such as heating oil EL and diesel fuel are of particular importance.
- the mixture of terpolymer and copolymer is added to mineral oils or mineral oil distillates in the form of solutions which contain 20 to 70% by weight (based on the solution) of the polymers.
- Suitable solvents are aliphatic or aromatic hydrocarbons or hydrocarbon mixtures, e.g. Gasoline fractions. Kerosene is particularly suitable.
- the amount of polymer based on mineral oil or mineral oil distillates should be 0.001 to 2, preferably 0.005 to 0.5% by weight.
- the polymer mixtures can be used alone or together with other additives, e.g. with other pour point depressants or dewaxing aids, with corrosion inhibitors, antioxidants, sludge inhibitors and additives to lower the cloud point.
- additives e.g. with other pour point depressants or dewaxing aids, with corrosion inhibitors, antioxidants, sludge inhibitors and additives to lower the cloud point.
- the vinyl acetate content in the polymer is determined using the pyrolysis method. For this purpose, 200 mg of the polymer are heated with 300 mg of pure polyethylene in a pyrolysis flask to 450 ° C. for 5 minutes and the cracked gases are collected in a 250 ml round-bottom flask. The resulting acetic acid is reacted with a NaJ / KJO3 solution and the iodine released is titrated with Na2S2O3 solution. The diisobutylene content in the polymer is determined by 13 C-NMR spectroscopy.
- Table 2 summarizes the results which describe the effectiveness of the process according to the invention for improving the flowability of mineral oils and mineral oil distillates.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Claims (3)
- Procédé pour améliorer la fluidité d'huiles minérales et de leurs distillats, caractérisé en ce que l'on ajoute aux huiles minérales ou à leurs distillats des mélanges d'un copolymère ternaire éthylène-acétate de vinyle-diisobutylène et d'un copolymère éthylène-acétate de vinyle, à des proportions relatives de 100:1 à 1:1, de préférence de 20:1 à 3:1, entre le copolymère ternaire et le copolymère, le copolymère ternaire éthylène-acétate de vinyle-diisobutylène contenant de 25 à 78, plus spécialement de 35 à 55 parties en poids d'acétate de vinyle et de 0,5 à 45, plus spécialement de 1,0 à 27,5 parties en poids de diisobutylène pour 100 parties en poids d'éthylène, ayant une masse moléculaire moyenne (mesurée par osmométrie de pression de vapeur) de 500 à 10 000, de préférence de 1 000 à 5 000 et plus spécialement de 1 500 à 3 500 g.mol -1 et contenant dans les chaînes latérales, pour 100 groupes CH₂, de 6 à 20, de préférence de 7 à 15 groupes CH₃ ne provenant pas du radical acétate de l'acétate de vinyle, et le copolymère éthylène-acétate de vinyle contenant de 5 à 54, plus spécialement de 11 à 33 parties en poids d'acétate de vinyle pour 100 parties en poids d'éthylène, ayant une masse moléculaire moyenne (mesurée par osmométrie de pression de vapeur) de 500 à 10 000, plus spécialement de 1 000 à 5 000 g.mol-1 et contenant dans les chaînes latérales, pour 100 groupes cH₂, de 1 à 10, de préférence de 3 à 7 groupes CH₃ ne provenant pas du radical acétate de l'acétate de vinyle.
- Huile minérale ou distillat d'huile minérale ayant une fluidité améliorée, caractérisés en ce qu'ils contiennent de 0,001 à 2, de préférence de 0,005 à 0,5 % de leurs poids d'un mélange consistant en un copolymère ternaire éthylène-acétate de vinyle-diisobutylène et un copolymère éthylène-acétate de vinyle dans des proportions relatives en poids de 100:1 à 1:1, de préférence de 20:1 à 3:1.
- Huile minérale ou distillat d'huile minérale selon la revendication 2, caractérisés en ce que :- le copolymère ternaire éthylène-acétate de vinyle-diisobutylène contient de 25 à 78, plus spécialement de 30 à 55 parties en poids d'acétate de vinyle et de 0,5 à 45, plus spécialement de 1,0 à 27,5 parties en poids de diisobutylène pour 100 parties en poids d'éthylène, il a une masse moléculaire moyenne (mesurée par osmométrie de pression de vapeur) de 500 à 10 000, de préférence de 1 000 à 5 000 et plus spécialement de 1 500 à 3 500 g.mol-1 et il contient dans les chaînes latérales, pour 100 groupes CH₂, de 6 à 20, de préférence de 7 à 15 groupes cH₃ qui ne proviennent pas du radical acétate de l'acétate de vinyle,- le copolymère éthylène-acétate de vinyle contient de 5 à 54, plus spécialement de 11 à 33 parties en poids d'acétate de vinyle pour 100 parties en poids d'éthylène, il a une masse moléculaire moyenne (mesurée par osmométrie de pression de vapeur) de 500 à 10 000, plus spécialement de 1 000 à 5 000 g.mol-1 et il contient dans les chaînes latérales, pour 100 groupes CH₂, de 1 à 10, de préférence de 3 à 7 groupes CH₃ ne provenant pas du radical acétate de l'acétate de vinyle.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT87110581T ATE64409T1 (de) | 1986-07-25 | 1987-07-22 | Verfahren zur verbesserung der fliessfaehigkeit von mineraloelen und mineraloeldestillaten. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19863625174 DE3625174A1 (de) | 1986-07-25 | 1986-07-25 | Verfahren zur verbesserung der fliessfaehigkeit von mineraloelen und mineraloeldestillaten |
DE3625174 | 1986-07-25 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0254284A1 EP0254284A1 (fr) | 1988-01-27 |
EP0254284B1 true EP0254284B1 (fr) | 1991-06-12 |
Family
ID=6305966
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP87110581A Expired - Lifetime EP0254284B1 (fr) | 1986-07-25 | 1987-07-22 | Procédé pour améliorer la fluidité d'huiles minérales et de distillats d'huile minérales |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0254284B1 (fr) |
AT (1) | ATE64409T1 (fr) |
DE (2) | DE3625174A1 (fr) |
ES (1) | ES2023855B3 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO2010081634A1 (fr) | 2009-01-13 | 2010-07-22 | Evonik Rohmax Additives Gmbh | Compositions de carburant ayant un point de trouble amélioré et des propriétés améliorées au stockage |
WO2011095249A1 (fr) | 2010-02-05 | 2011-08-11 | Evonik Rohmax Additives Gmbh | Composition ayant une filtrabilité améliorée |
DE10155774B4 (de) | 2001-11-14 | 2020-07-02 | Clariant Produkte (Deutschland) Gmbh | Additive für schwefelarme Mineralöldestillate, umfassend einen Ester alkoxylierten Glycerins und einen polaren stickstoffhaltigen Paraffindispergator |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3922146A1 (de) * | 1989-07-06 | 1991-01-17 | Roehm Gmbh | Additive fuer dieselkraftstoff |
CN1035676C (zh) * | 1991-12-12 | 1997-08-20 | 中国石油化工总公司石油化工科学研究院 | 柴油流动改进剂的制备方法 |
GB9213871D0 (en) † | 1992-06-30 | 1992-08-12 | Exxon Chemical Patents Inc | Oil additives and compositions |
DE19620118C1 (de) * | 1996-05-18 | 1997-10-23 | Hoechst Ag | Terpolymerisate des Ethylens, ihre Herstellung und ihre Verwendung als Additive für Mineralöldestillate |
DE19620119C1 (de) * | 1996-05-18 | 1997-10-23 | Hoechst Ag | Terpolymerisate des Ethylens, ihre Herstellung und ihre Verwendung als Additive für Mineralöldestillate |
US5681359A (en) * | 1996-10-22 | 1997-10-28 | Quantum Chemical Corporation | Ethylene vinyl acetate and isobutylene terpolymer as a cold flow improver for distillate fuel compositions |
DE19729056C1 (de) * | 1997-07-08 | 1998-12-03 | Clariant Gmbh | Fließverbesserer für Mineralöle |
DE19739271A1 (de) * | 1997-09-08 | 1999-03-11 | Clariant Gmbh | Additiv zur Verbesserung der Fließfähigkeit von Mineralölen und Mineralöldestillaten |
DE19802690C2 (de) * | 1998-01-24 | 2003-02-20 | Clariant Gmbh | Additiv zur Verbesserung der Kaltfließeigenschaften von Brennstoffölen |
DE19823565A1 (de) | 1998-05-27 | 1999-12-02 | Clariant Gmbh | Mischungen von Copolymeren mit verbesserter Schmierwirkung |
EP1294832B1 (fr) | 2000-06-15 | 2004-09-08 | Clariant International Ltd. | Additif pour ameliorer la fuidite a froid et la stabilite au stockage du petrole brut |
DE10155747B4 (de) | 2001-11-14 | 2008-09-11 | Clariant Produkte (Deutschland) Gmbh | Additive für schwefelarme Mineralöldestillate, umfassend einen Ester eines alkoxylierten Polyols und ein Alkylphenol-Aldehydharz |
US6673131B2 (en) | 2002-01-17 | 2004-01-06 | Equistar Chemicals, Lp | Fuel additive compositions and distillate fuels containing same |
EP1380635B1 (fr) | 2002-07-09 | 2013-01-23 | Clariant Produkte (Deutschland) GmbH | Agent d'amélioration de l'écoulement à froid pour huiles combustibles d'origine animale ou végétale. |
DE10349851B4 (de) | 2003-10-25 | 2008-06-19 | Clariant Produkte (Deutschland) Gmbh | Kaltfließverbesserer für Brennstofföle pflanzlichen oder tierischen Ursprungs |
DE10349850C5 (de) | 2003-10-25 | 2011-12-08 | Clariant Produkte (Deutschland) Gmbh | Kaltfließverbesserer für Brennstofföle pflanzlichen oder tierischen Ursprungs |
DE10357878C5 (de) | 2003-12-11 | 2013-07-25 | Clariant Produkte (Deutschland) Gmbh | Brennstofföle aus Mitteldestillaten und Ölen pflanzlichen oder tierischen Ursprungs mit verbesserten Kälteeigenschaften |
DE10357880B4 (de) | 2003-12-11 | 2008-05-29 | Clariant Produkte (Deutschland) Gmbh | Brennstofföle aus Mitteldestillaten und Ölen pflanzlichen oder tierischen Ursprungs mit verbesserten Kälteeigenschaften |
ITMI20132043A1 (it) | 2013-12-06 | 2015-06-07 | Eni Spa | Composizioni a base di copolimeri etilene-vinilacetato e loro impiego come additivi anti-gelificazione di greggi petroliferi paraffinici |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1914756C3 (de) * | 1968-04-01 | 1985-05-15 | Exxon Research and Engineering Co., Linden, N.J. | Verwendung von Ethylen-Vinylacetat- Mischpolymerisaten für Erdöl-Destillate |
JPH0710900B2 (ja) * | 1982-06-18 | 1995-02-08 | エクソン リサーチ アンド エンヂニアリング コムパニー | 中級蒸留物燃料油用流動性改良剤 |
CA1263663C (fr) * | 1984-12-06 | 1989-12-05 | Terpolymeres d'ethylene, d'acetate de vinyle et d'isobutylene, additifs abaissant le point d'ecoulement dans les hydrocarbures distilles | |
DE3501384A1 (de) * | 1985-01-17 | 1986-07-17 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur verbesserung der fliessfaehigkeit von mineraloelen und mineraloeldestillaten |
US4746327A (en) * | 1985-03-25 | 1988-05-24 | Standard Oil Company (Indiana) | Ethylene-unsaturated, ester-substituted olefin terpolymer flow improvers |
DE3616056A1 (de) * | 1985-05-29 | 1986-12-04 | Hoechst Ag, 65929 Frankfurt | Verwendung von ethylen-terpolymerisaten als additive fuer mineraloele und mineraloeldestillate |
-
1986
- 1986-07-25 DE DE19863625174 patent/DE3625174A1/de not_active Withdrawn
-
1987
- 1987-07-22 EP EP87110581A patent/EP0254284B1/fr not_active Expired - Lifetime
- 1987-07-22 AT AT87110581T patent/ATE64409T1/de not_active IP Right Cessation
- 1987-07-22 ES ES87110581T patent/ES2023855B3/es not_active Expired - Lifetime
- 1987-07-22 DE DE8787110581T patent/DE3770711D1/de not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
DE10155774B4 (de) | 2001-11-14 | 2020-07-02 | Clariant Produkte (Deutschland) Gmbh | Additive für schwefelarme Mineralöldestillate, umfassend einen Ester alkoxylierten Glycerins und einen polaren stickstoffhaltigen Paraffindispergator |
WO2010081634A1 (fr) | 2009-01-13 | 2010-07-22 | Evonik Rohmax Additives Gmbh | Compositions de carburant ayant un point de trouble amélioré et des propriétés améliorées au stockage |
WO2011095249A1 (fr) | 2010-02-05 | 2011-08-11 | Evonik Rohmax Additives Gmbh | Composition ayant une filtrabilité améliorée |
Also Published As
Publication number | Publication date |
---|---|
DE3770711D1 (de) | 1991-07-18 |
EP0254284A1 (fr) | 1988-01-27 |
ATE64409T1 (de) | 1991-06-15 |
DE3625174A1 (de) | 1988-01-28 |
ES2023855B3 (es) | 1992-02-16 |
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