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 PDF

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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
Application number
EP88120410A
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German (de)
English (en)
French (fr)
Other versions
EP0320766A2 (de
EP0320766A3 (en
Inventor
Herbert Dr. Wirtz
Michael Dr. Feustel
Juliane Balzer
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Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
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Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0320766A2 publication Critical patent/EP0320766A2/de
Publication of EP0320766A3 publication Critical patent/EP0320766A3/de
Application granted granted Critical
Publication of EP0320766B1 publication Critical patent/EP0320766B1/de
Anticipated expiration legal-status Critical
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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/143Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/146Macromolecular compounds according to different macromolecular groups, mixtures thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/16Hydrocarbons
    • C10L1/1625Hydrocarbons macromolecular compounds
    • C10L1/1633Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
    • C10L1/1641Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/195Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197Macromolecular 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
    • C10L1/1973Macromolecular 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/234Macromolecular compounds
    • C10L1/236Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • C10L1/2364Macromolecular 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

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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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Fats And Perfumes (AREA)
EP88120410A 1987-12-16 1988-12-07 Polymermischungen für die Verbesserung der Fliessfähigkeit von Mineralöldestillaten in der Kälte Revoked EP0320766B1 (de)

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)

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DE102004014080A1 (de) * 2004-03-23 2005-10-13 Peter Dr. Wilharm Nukleierungsmittel auf der Basis von hyperverzweigten Polymeren

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DE3616056A1 (de) * 1985-05-29 1986-12-04 Hoechst Ag, 65929 Frankfurt Verwendung von ethylen-terpolymerisaten als additive fuer mineraloele und mineraloeldestillate
FR2592387B1 (fr) * 1985-12-30 1988-04-08 Inst Francais Du Petrole Compositions d'additifs destinees notamment a ameliorer les proprietes de filtrabilite a froid des distillats moyens de petrole

Cited By (1)

* Cited by examiner, † Cited by third party
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

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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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