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EP1134274A3 - Blends of carboxylic acids, derivatives thereof and hydroxyl groups carrying polymers, and use thereof to improve the lubricating activity of oils - Google Patents

Blends of carboxylic acids, derivatives thereof and hydroxyl groups carrying polymers, and use thereof to improve the lubricating activity of oils Download PDF

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Publication number
EP1134274A3
EP1134274A3 EP01104846A EP01104846A EP1134274A3 EP 1134274 A3 EP1134274 A3 EP 1134274A3 EP 01104846 A EP01104846 A EP 01104846A EP 01104846 A EP01104846 A EP 01104846A EP 1134274 A3 EP1134274 A3 EP 1134274A3
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Prior art keywords
und
bis
oder
radical
mol
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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.)
Granted
Application number
EP01104846A
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German (de)
French (fr)
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EP1134274A2 (en
EP1134274B1 (en
Inventor
Matthias Dr. Krull
Werner Dr. Reimann
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Clariant Produkte Deutschland GmbH
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Clariant GmbH
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Publication of EP1134274A3 publication Critical patent/EP1134274A3/en
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Publication of EP1134274B1 publication Critical patent/EP1134274B1/en
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    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/08Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Gegenstand der Erfindung sind Additive zur Verbesserung von Schmiereigenschaften von Brennstoffölen, enthaltend

  • A) 10 - 95 Gew.-% mindestens eines öllöslichen Amphiphils der Formeln 1
    Figure 80000001
    und/oder 2 R1― X ― R2 worin R1 einen Alkyl-, Alkenyl-, Hydroxyalkyl- oder aromatischen Rest mit 1 bis 50 Kohlenstoffatomen, X NH, NR3, O oder S, y = 1, 2, 3 oder 4, R2 Wasserstoff oder einen Hydroxylgruppen tragenden Alkylrest mit 2 bis 10 Kohlenstoffatomen und R3 einen Stickstoff und/oder Hydroxylgruppen tragenden Alkylrest mit 2 bis 10 Kohlenstoffatomen oder einen C1-C20-Alkylrest bedeutet, oder XR2 gleich NR41R42 bedeutet, worin R41 eine Rest der Formel 3a -(R43-NR44)m-R45 und R42 eine Rest der Formel 3b -(R43-NR44)n-R45 bedeutet, R43 für eine C2- bis C-10-Alkylengruppe steht, R44 Wasserstoff, Methyl, C2- bis C10--Alkyl, eine Rest der Formel 3c R1-CO- oder einen Alkoxyrest, und R45 Wasserstoff oder einen Rest der Formel 3c bedeutet, und m und n jeweils unabhängig voneinander eine ganze Zahl von 0 bis 20 bedeuten, und
  • B) 5-90 Gew.-% mindestens eines Copolymers, welches
  • B1) 5 bis 80 mol-% Struktureinheiten, die sich von olefinisch ungesättigten Verbindungen ableiten, welche mindestens eine freie Hydroxylgruppe aufweisen, und
  • B2) 20 bis 95 mol-% Struktureinheiten, die sich von olefinisch ungesättigten Verbindungen ableiten, welche einen Kohlenwasserstoffrest mit mindestens 6 Kohlenstoffatomen tragen, sowie gegebenenfalls
  • B3) 0 bis 40 mol-% weiterer Struktureinheiten ausgewählt aus der Gruppe bestehend aus (Meth)acrylsäure, (Meth)acrylaten, Vinylestern, Vinylethern und Alkenen, mit der Maßgabe, dass die unter B3) genannten Struktureinheiten von den unter B1) und B2) genannten Struktureinheiten verschieden sind,
  • und das Copolymer eine mittlere Molekülmasse Mw von 500 bis 100.000 g/mol und eine OH-Zahl zwischen 10 und 350 mg KOH/g aufweist.The invention relates to additives for improving the lubricating properties of fuel oils
  • A) 10 to 95% by weight of at least one oil-soluble amphiphile of the formula 1
    Figure 80000001
    and / or 2 R 1 - X - R 2 wherein R 1 is an alkyl, alkenyl, hydroxyalkyl or aromatic radical having 1 to 50 carbon atoms, X NH, NR 3 , O or S, y = 1, 2, 3 or 4, R 2 is hydrogen or an alkyl radical carrying hydroxyl groups 2 to 10 carbon atoms and R 3 is a nitrogen and / or hydroxyl-bearing alkyl radical having 2 to 10 carbon atoms or a C 1 -C 20 alkyl radical, or XR 2 is NR 41 R 42 , in which R 41 is a radical of the formula 3a - (R 43 -NR 44 ) m -R 45 and R 42 is a radical of the formula 3b - (R 43 -NR 44 ) n -R 45 means R 43 represents a C 2 -C 10 -alkylene group, R 44 is hydrogen, methyl, C 2 -C 10 -alkyl, a radical of the formula 3c R 1 -CO- or an alkoxy radical, and R 45 is hydrogen or a radical of the formula 3c, and m and n each independently represent an integer from 0 to 20, and
  • B) 5-90% by weight of at least one copolymer which
  • B1) 5 to 80 mol% of structural units which are derived from olefinically unsaturated compounds which have at least one free hydroxyl group, and
  • B2) 20 to 95 mol% of structural units which are derived from olefinically unsaturated compounds which carry a hydrocarbon radical having at least 6 carbon atoms, and, if appropriate
  • B3) 0 to 40 mol% of further structural units selected from the group consisting of (meth) acrylic acid, (meth) acrylates, vinyl esters, vinyl ethers and alkenes, with the proviso that the structural units mentioned under B3) differ from those under B1) and B2 ) structural units mentioned are different,
  • and the copolymer has an average molecular weight Mw of 500 to 100,000 g / mol and an OH number between 10 and 350 mg KOH / g.

    EP01104846A 2000-03-16 2001-02-28 Use of carboxylic acids and derivatives thereof as solvent for hydroxyl groups carrying polymers Expired - Lifetime EP1134274B1 (en)

    Applications Claiming Priority (2)

    Application Number Priority Date Filing Date Title
    DE10012947A DE10012947A1 (en) 2000-03-16 2000-03-16 Mixtures of carboxylic acids, their derivatives and hydroxyl-containing polymers, and their use to improve the lubricating effect of oils
    DE10012947 2000-03-16

    Publications (3)

    Publication Number Publication Date
    EP1134274A2 EP1134274A2 (en) 2001-09-19
    EP1134274A3 true EP1134274A3 (en) 2002-03-06
    EP1134274B1 EP1134274B1 (en) 2006-11-29

    Family

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    Family Applications (1)

    Application Number Title Priority Date Filing Date
    EP01104846A Expired - Lifetime EP1134274B1 (en) 2000-03-16 2001-02-28 Use of carboxylic acids and derivatives thereof as solvent for hydroxyl groups carrying polymers

    Country Status (7)

    Country Link
    US (1) US6461393B1 (en)
    EP (1) EP1134274B1 (en)
    JP (1) JP2001294876A (en)
    AT (1) ATE346900T1 (en)
    CA (1) CA2340849A1 (en)
    DE (2) DE10012947A1 (en)
    NO (1) NO20011311L (en)

    Families Citing this family (12)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    DE10136828B4 (en) * 2001-07-27 2005-12-15 Clariant Gmbh Lubricating additives with reduced emulsifying tendency for highly desulphurised fuel oils
    ITMI20030628A1 (en) * 2003-03-31 2004-10-01 Cam Tecnologie S P A AUTOMOTIVE FUEL.
    DE10319028B4 (en) * 2003-04-28 2006-12-07 Clariant Produkte (Deutschland) Gmbh Demulsifiers for mixtures of middle distillates with fuel oils of vegetable or animal origin
    DE10349850C5 (en) 2003-10-25 2011-12-08 Clariant Produkte (Deutschland) Gmbh Cold flow improver for fuel oils of vegetable or animal origin
    DE10349851B4 (en) * 2003-10-25 2008-06-19 Clariant Produkte (Deutschland) Gmbh Cold flow improver for fuel oils of vegetable or animal origin
    DE10357877B4 (en) * 2003-12-11 2008-05-29 Clariant Produkte (Deutschland) Gmbh Fuel oils from middle distillates and oils of vegetable or animal origin with improved cold properties
    DE10357880B4 (en) * 2003-12-11 2008-05-29 Clariant Produkte (Deutschland) Gmbh Fuel oils from middle distillates and oils of vegetable or animal origin with improved cold properties
    DE10357878C5 (en) * 2003-12-11 2013-07-25 Clariant Produkte (Deutschland) Gmbh Fuel oils from middle distillates and oils of vegetable or animal origin with improved cold properties
    US20050138859A1 (en) * 2003-12-16 2005-06-30 Graham Jackson Cold flow improver compositions for fuels
    DE102004024532B4 (en) * 2004-05-18 2006-05-04 Clariant Gmbh Demulsifiers for mixtures of middle distillates with fuel oils of vegetable or animal origin and water
    US7185699B2 (en) * 2004-05-25 2007-03-06 Schlumberger Technology Corporation Water compatible hydraulic fluids
    US8029579B2 (en) * 2006-06-28 2011-10-04 COH Inc. Fatty acid blends and uses therefor

    Citations (7)

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    Publication number Priority date Publication date Assignee Title
    EP0523672A2 (en) * 1991-07-18 1993-01-20 Hoechst Aktiengesellschaft Esters of copolymers of ethylenic unsaturated carboxylic acid and polyoxyalkylenether of lower, unsaturated alcohols as flow improvers of paraffin-containing oils
    EP0688796A1 (en) * 1994-06-24 1995-12-27 Hoechst Aktiengesellschaft Reaction products of polyetheramines with polymers of alpha, beta- unsaturated dicarboxylic acids
    EP0807676A2 (en) * 1996-05-17 1997-11-19 Ethyl Petroleum Additives Limited Fuel additives and compositions
    EP0900836A1 (en) * 1997-09-08 1999-03-10 Clariant GmbH Additive for mineral oils and mineral oil distillates flowability improvement
    WO1999027037A1 (en) * 1997-11-21 1999-06-03 Rohmax Additives Gmbh Additive for biodiesel and biofuel oils
    EP0960908A1 (en) * 1998-05-27 1999-12-01 Clariant GmbH Blends of copolymers with improved lubricating activity
    WO2000078897A1 (en) * 1999-06-17 2000-12-28 Clariant Gmbh Use of hydroxyl group-containing copolymers for producing fuel oils with improved lubricity

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    GB1047493A (en) * 1963-01-30
    US4015063A (en) * 1974-11-11 1977-03-29 Standard Oil Company (Indiana) Crude oils and residual fuel oils containing a terpolymer of ethylene, vinyl ester, and dialkylvinyl carbinol
    US4211534A (en) 1978-05-25 1980-07-08 Exxon Research & Engineering Co. Combination of ethylene polymer, polymer having alkyl side chains, and nitrogen containing compound to improve cold flow properties of distillate fuel oils
    DE3405843A1 (en) 1984-02-17 1985-08-29 Bayer Ag, 5090 Leverkusen COPOLYMERS BASED ON MALEINIC ACID ANHYDRIDE AND (ALPHA), (BETA) -UNAUSAUTED COMPOUNDS, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS PARAFFIN INHIBITORS
    EP0153176B1 (en) 1984-02-21 1991-11-27 Exxon Research And Engineering Company Middle distillate compositions with improved cold flow properties
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    DE59404053D1 (en) 1993-01-06 1997-10-23 Hoechst Ag Terpolymers based on alpha, beta-unsaturated dicarboxylic anhydrides, alpha, beta-unsaturated compounds and polyoxyalkylene ethers of lower, unsaturated alcohols
    GB9301119D0 (en) * 1993-01-21 1993-03-10 Exxon Chemical Patents Inc Fuel composition
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    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    EP0523672A2 (en) * 1991-07-18 1993-01-20 Hoechst Aktiengesellschaft Esters of copolymers of ethylenic unsaturated carboxylic acid and polyoxyalkylenether of lower, unsaturated alcohols as flow improvers of paraffin-containing oils
    EP0688796A1 (en) * 1994-06-24 1995-12-27 Hoechst Aktiengesellschaft Reaction products of polyetheramines with polymers of alpha, beta- unsaturated dicarboxylic acids
    EP0807676A2 (en) * 1996-05-17 1997-11-19 Ethyl Petroleum Additives Limited Fuel additives and compositions
    EP0900836A1 (en) * 1997-09-08 1999-03-10 Clariant GmbH Additive for mineral oils and mineral oil distillates flowability improvement
    WO1999027037A1 (en) * 1997-11-21 1999-06-03 Rohmax Additives Gmbh Additive for biodiesel and biofuel oils
    EP0960908A1 (en) * 1998-05-27 1999-12-01 Clariant GmbH Blends of copolymers with improved lubricating activity
    WO2000078897A1 (en) * 1999-06-17 2000-12-28 Clariant Gmbh Use of hydroxyl group-containing copolymers for producing fuel oils with improved lubricity

    Also Published As

    Publication number Publication date
    JP2001294876A (en) 2001-10-23
    DE10012947A1 (en) 2001-09-27
    EP1134274A2 (en) 2001-09-19
    NO20011311L (en) 2001-09-17
    ATE346900T1 (en) 2006-12-15
    CA2340849A1 (en) 2001-09-16
    EP1134274B1 (en) 2006-11-29
    DE50111515D1 (en) 2007-01-11
    US6461393B1 (en) 2002-10-08
    NO20011311D0 (en) 2001-03-15

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