EP0320766B1 - Polymermischungen für die Verbesserung der Fliessfähigkeit von Mineralöldestillaten in der Kälte - Google Patents
Polymermischungen für die Verbesserung der Fliessfähigkeit von Mineralöldestillaten in der Kälte Download PDFInfo
- Publication number
- EP0320766B1 EP0320766B1 EP88120410A EP88120410A EP0320766B1 EP 0320766 B1 EP0320766 B1 EP 0320766B1 EP 88120410 A EP88120410 A EP 88120410A EP 88120410 A EP88120410 A EP 88120410A EP 0320766 B1 EP0320766 B1 EP 0320766B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- copolymer
- vinyl acetate
- gew
- ethylene
- 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.)
- Revoked
Links
- 229920002959 polymer blend Polymers 0.000 title claims description 12
- 239000003208 petroleum Substances 0.000 title 1
- 229920001577 copolymer Polymers 0.000 claims description 30
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 20
- 239000004711 α-olefin Substances 0.000 claims description 18
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000002480 mineral oil Substances 0.000 claims description 3
- 235000010446 mineral oil Nutrition 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 14
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 10
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 10
- 239000005038 ethylene vinyl acetate Substances 0.000 description 9
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 229920001897 terpolymer Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 239000000446 fuel Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- -1 stearyl alcohols Chemical class 0.000 description 3
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 3
- NWODYZCQADERLP-HNENSFHCSA-N (z)-4-(octadecylamino)-4-oxobut-2-enoic acid Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)\C=C/C(O)=O NWODYZCQADERLP-HNENSFHCSA-N 0.000 description 2
- HOLZCMFSCBLOLX-UHFFFAOYSA-N 1-octadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O HOLZCMFSCBLOLX-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- BLHDYAXSQWGYSM-UHFFFAOYSA-N 3-octadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(=O)NC1=O BLHDYAXSQWGYSM-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012619 stoichiometric conversion Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
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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
-
- 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
- C10L1/16—Hydrocarbons
- C10L1/1625—Hydrocarbons macromolecular compounds
- C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
- C10L1/1641—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
- C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
Definitions
- Mineral oil distillates such as diesel fuel or heating oil contain different amounts of long-chain n-paraffins depending on the provenance of the base crude oil and depending on the processing method in the refinery.
- n-paraffins crystallize when the saturation temperature falls below the orthorhombic crystal lattice in the form of thin trapezoidal or diamond-shaped platelets and thin needles. These crystal modifications tend to grow together and agglomerate, which leads to the formation of a three-dimensional network.
- the crystallization of the n-paraffins is accompanied by a decrease in fluidity and an increase in viscosity. As a result, blockages of the filters can occur in diesel engines and combustion systems, which impair safe metering of the fuel and, in the worst case, completely block the fuel supply.
- n-paraffins / flow improvers adducts enable smooth operation of diesel engines and fuel systems even at low temperatures.
- additives or flow improvers mainly copolymers of ethylene and vinyl acetate (EVA copolymers) in various variations are used to improve the low-temperature stability of diesel fuels and heating oil.
- This category includes Middle distillates with a high boiling point (S.E.> 380 ° C).
- the cloud point (CP) of such oils is often significantly above CP: ⁇ 0 ° C.
- EVA copolymers with different molecular weights and different vinyl acetate contents are described (DT-OS 2 206 719).
- additives of polymeric substances of different composition such as polyacrylates (US-A-4 058 371), ethylene- ⁇ -olefin copolymers (BE-Pat. 749 254) and esters of stearyl alcohols (FR-Pat. 2 114 718).
- polyacrylates US-A-4 058 371
- BE-Pat. 749 254 ethylene- ⁇ -olefin copolymers
- FR-Pat. 2 114 718 esters of stearyl alcohols
- reaction products of ⁇ -olefins, acrylic acid esters and maleic acid derivatives with amines is also known.
- FR-A-2 592 387 describes a process for the preparation of terpolymers based on vinyl ethers, C20-C24- ⁇ -olefins and N-alkylmaleimides with long-chain alkyl groups, which consists of two successive steps.
- a mixture is first made 15-40 mol% of ⁇ -olefin, 20-60 mol% of unsaturated ⁇ , ⁇ -dicarboxylic acid and 15-60 mol% of at least one vinyl ester, a saturated aliphatic monocarboxylic acid and / or at least one alkyl ether, cycloalkyl ether or vinyl ether in a solvent, such as toluene or xylene, in the presence of a suitable radical initiator, such as azo-bis-isobutyronitrile, polymerized at temperatures of 70-200 ° C, preferably 80-150 ° C, over a period of 2-14 hours.
- a suitable radical initiator such as azo-bis-isobutyronitrile
- the invention relates to polymer mixtures of a copolymer (A1) made of 10-60% by weight vinyl acetate and 40-90% by weight ethylene or a copolymer (A2) made of 15-50% by weight Vinyl acetate, 0.5-20% by weight of C6-C24- ⁇ -olefin and 30 - 70% by weight of ethylene and a copolymer (B) of 10-90% by weight of C6-C24- ⁇ -olefin and 10-90 % N-C6-C22-alkylmaleimide, the mixing ratio of the copolymers (A1) or (A2) to (B) being 100: 1 to 1: 1.
- the copolymers mentioned under A1 and A2 are obtained via high pressure synthesis (reaction pressure: 100-200 MPa; reaction temperature: 120-280 ° C) in a bulk polymerization according to methods known per se.
- the polymer (A1) are preferred those containing 15-40 wt .-% vinyl acetate and accordingly 60-85 wt .-% ethylene.
- the polymer (A2) preferably contains 20 to 30 wt .-% vinyl acetate and 2 to 5 wt .-% ⁇ -olefin. Polymers of this type are partially described in DE-PS 21 02 469 and are produced by the processes described there.
- the copolymers (B) preferably contain 50% by weight of the ⁇ -olefin and 50% by weight of the N-alkylmaleimide.
- the ⁇ -olefins preferably contain 8-18 C atoms, the alkyl group in the N-alkylmaleimides preferably contains 12-22 C atoms.
- the copolymers mentioned under (B) are obtained by solution polymerization of N-alkylmaleimides and ⁇ -olefins at 120 ° C. using typical radical initiators such as tert-butyl perbenzoate or azobisisobutyronitrile.
- the monomeric maleimide is obtained beforehand by stoichiometric conversion of maleic anhydride and the corresponding amine at 120-150 ° C. using an aromatic hydrocarbon such as toluene or xylene as an entrainer and p-toluenesulfonic acid as a catalyst. The progress of the reaction can be determined via the acid number.
- the ⁇ -olefin and the free-radical catalyst are then added to this solution and polymerization is carried out by heating to approximately 100-140 ° C.
- this polymerization can also be carried out in the melt without solvent, with the solvent which was required for the preparation of the N-alkylmaleimide was distilled off before the polymerization.
- the average molecular weight of all three copolymers is about 1000 to 10000 g mol ⁇ 1.
- the mixing ratio of the polymers (A1) or (A2) to (B) is 100: 1 to 1: 1, preferably 10: 1 to 6: 1 parts by weight.
- the polymer mixtures according to the invention are produced by simply mixing the individual components.
- the polymer mixtures described are notable for their very broad activity and also enable the cold properties of the problem oils mentioned at the beginning to be improved.
- the polymer mixtures are added to the petroleum distillates in amounts of approximately 10 to 500 ppm.
- Example II.1 200 g of the solution prepared according to Example I.2 are initially charged with 200 g of a mixture of C20-, C22- and C24- ⁇ -olefins and heated to 120 ° C. A mixture of 2 g of t-butylbenzoyl peroxide in 40 g of toluene is added dropwise over 20 minutes and the mixture is then kept at 140 ° C. for a further 2 hours.
- Example II.1 specified rule 200 g of the solution prepared according to Example I.3 submitted with 200 g of C18- ⁇ -olefin (octadecene) and heated to 120 ° C. A mixture of 2 g of AIBN in 40 g of toluene is added dropwise over 20 minutes and the mixture is then kept at 120 ° C. for 2 hours
Landscapes
- 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)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19873742630 DE3742630A1 (de) | 1987-12-16 | 1987-12-16 | Polymermischungen fuer die verbesserung der fliessfaehigkeit von mineraloeldestillaten in der kaelte |
DE3742630 | 1987-12-16 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0320766A2 EP0320766A2 (de) | 1989-06-21 |
EP0320766A3 EP0320766A3 (en) | 1989-12-20 |
EP0320766B1 true EP0320766B1 (de) | 1994-01-12 |
Family
ID=6342734
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88120410A Revoked EP0320766B1 (de) | 1987-12-16 | 1988-12-07 | Polymermischungen für die Verbesserung der Fliessfähigkeit von Mineralöldestillaten in der Kälte |
Country Status (8)
Country | Link |
---|---|
US (1) | US4985048A (fi) |
EP (1) | EP0320766B1 (fi) |
JP (1) | JP2777810B2 (fi) |
CA (1) | CA1337888C (fi) |
DE (2) | DE3742630A1 (fi) |
ES (1) | ES2061616T3 (fi) |
FI (1) | FI97234C (fi) |
NO (1) | NO174261C (fi) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004014080A1 (de) * | 2004-03-23 | 2005-10-13 | Peter Dr. Wilharm | Nukleierungsmittel auf der Basis von hyperverzweigten Polymeren |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
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DE4241948A1 (de) * | 1992-12-12 | 1994-06-16 | Hoechst Ag | Pfropfpolymerisate, ihre Herstellung und Verwendung als Stockpunkterniedriger und Fließverbesserer für Rohöle, Rückstandsöle und Mitteldestillate |
DE4430294A1 (de) * | 1994-08-26 | 1996-02-29 | Basf Ag | Polymermischungen und ihre Verwendung als Zusatz für Erdölmitteldestillate |
US6846338B2 (en) | 1997-07-08 | 2005-01-25 | Clariant Gmbh | Fuel oils based on middle distillates and copolymers of ethylene and unsaturated carboxylic esters |
DE19729057A1 (de) * | 1997-07-08 | 1999-01-14 | Clariant Gmbh | Copolymere auf Basis von Ethylen und ungesättigten Carbonsäureestern und ihre Verwendung als Mineralöladditive |
DE19754555A1 (de) | 1997-12-09 | 1999-06-24 | Clariant Gmbh | Verfahren zur Herstellung von Ethylen-Mischpolymerisaten und deren Verwendung als Zusatz zu Mineralöl und Mineralöldestillaten |
DE19757830C2 (de) | 1997-12-24 | 2003-06-18 | Clariant Gmbh | Brennstofföle mit verbesserter Schmierwirkung |
DE19802689A1 (de) * | 1998-01-24 | 1999-07-29 | Clariant Gmbh | Verfahren zur Verbesserung der Kaltfließeigenschaften von Brennstoffölen |
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 |
GB9826448D0 (en) * | 1998-12-02 | 1999-01-27 | Exxon Chemical Patents Inc | Fuel oil additives and compositions |
US6206939B1 (en) * | 1999-05-13 | 2001-03-27 | Equistar Chemicals, Lp | Wax anti-settling agents for distillate fuels |
US6203583B1 (en) * | 1999-05-13 | 2001-03-20 | Equistar Chemicals, Lp | Cold flow improvers for distillate fuel compositions |
DE19927561C1 (de) | 1999-06-17 | 2000-12-14 | Clariant Gmbh | Verwendung hydroxylgruppenhaltiger Copolymere zur Herstellung von Brennstoffölen mit verbesserter Schmierwirkung |
DE19927560C2 (de) | 1999-06-17 | 2002-03-14 | Clariant Gmbh | Brennstoffölzusammensetzung |
US6143043A (en) * | 1999-07-13 | 2000-11-07 | Equistar Chemicals, Lp | Cloud point depressants for middle distillate fuels |
US6495495B1 (en) | 1999-08-20 | 2002-12-17 | The Lubrizol Corporation | Filterability improver |
EP1116780B1 (de) | 2000-01-11 | 2005-08-31 | Clariant GmbH | Mehrfunktionelles Additiv für Brennstofföle |
DE10000649C2 (de) | 2000-01-11 | 2001-11-29 | Clariant Gmbh | Mehrfunktionelles Additiv für Brennstofföle |
DE10012269C2 (de) | 2000-03-14 | 2003-05-15 | Clariant Gmbh | Verwendung von Copolymermischungen als Additiv zur Verbesserung der Kaltfließeigenschaften von Mitteldestillaten |
DE10012267B4 (de) * | 2000-03-14 | 2005-12-15 | Clariant Gmbh | Copolymermischungen und ihre Verwendung als Additiv zur Verbesserung der Kaltfließeigenschaften von Mitteldestillaten |
DE10012946B4 (de) | 2000-03-16 | 2006-02-02 | Clariant Gmbh | Verwendung von öllöslichen Amphiphilen als Lösemittel für hydroxyfunktionelle Copolymere |
DE10012947A1 (de) | 2000-03-16 | 2001-09-27 | Clariant Gmbh | Mischungen aus Carbonsäuren, deren Derivate und hydroxylgruppenhaltigen Polymeren, sowie deren Verwendung zur Verbesserung der Schmierwirkung von Ölen |
DE10058356B4 (de) | 2000-11-24 | 2005-12-15 | Clariant Gmbh | Brennstofföle mit verbesserter Schmierwirkung, enthaltend Umsetzungsprodukte aus Fettsäuren mit kurzkettigen öllöslichen Aminen |
DE10058359B4 (de) | 2000-11-24 | 2005-12-22 | Clariant Gmbh | Brennstofföle mit verbesserter Schmierwirkung, enthaltend Mischungen aus Fettsäuren mit Paraffindispergatoren, sowie ein schmierverbesserndes Additiv |
DE10136828B4 (de) * | 2001-07-27 | 2005-12-15 | Clariant Gmbh | Schmierverbessernde Additive mit verminderter Emulgierneigung für hochentschwefelte Brennstofföle |
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 |
US6673131B2 (en) | 2002-01-17 | 2004-01-06 | Equistar Chemicals, Lp | Fuel additive compositions and distillate fuels containing same |
CA2431748C (en) * | 2002-07-09 | 2010-11-09 | Clariant Gmbh | Oxidation-stabilized oily liquids based on vegetable or animal oils |
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-
1987
- 1987-12-16 DE DE19873742630 patent/DE3742630A1/de not_active Withdrawn
-
1988
- 1988-12-07 EP EP88120410A patent/EP0320766B1/de not_active Revoked
- 1988-12-07 ES ES88120410T patent/ES2061616T3/es not_active Expired - Lifetime
- 1988-12-07 DE DE88120410T patent/DE3887115D1/de not_active Revoked
- 1988-12-14 US US07/284,085 patent/US4985048A/en not_active Expired - Lifetime
- 1988-12-14 FI FI885781A patent/FI97234C/fi not_active IP Right Cessation
- 1988-12-15 CA CA000585958A patent/CA1337888C/en not_active Expired - Fee Related
- 1988-12-15 JP JP63315202A patent/JP2777810B2/ja not_active Expired - Fee Related
- 1988-12-15 NO NO885579A patent/NO174261C/no unknown
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DE102004014080A1 (de) * | 2004-03-23 | 2005-10-13 | Peter Dr. Wilharm | Nukleierungsmittel auf der Basis von hyperverzweigten Polymeren |
Also Published As
Publication number | Publication date |
---|---|
DE3742630A1 (de) | 1989-06-29 |
CA1337888C (en) | 1996-01-02 |
FI885781A0 (fi) | 1988-12-14 |
FI885781A (fi) | 1989-06-17 |
FI97234B (fi) | 1996-07-31 |
EP0320766A2 (de) | 1989-06-21 |
NO174261B (no) | 1993-12-27 |
NO885579L (no) | 1989-06-19 |
JP2777810B2 (ja) | 1998-07-23 |
NO174261C (no) | 1994-04-06 |
ES2061616T3 (es) | 1994-12-16 |
DE3887115D1 (de) | 1994-02-24 |
FI97234C (fi) | 1996-11-11 |
US4985048A (en) | 1991-01-15 |
NO885579D0 (no) | 1988-12-15 |
EP0320766A3 (en) | 1989-12-20 |
JPH01201348A (ja) | 1989-08-14 |
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