EP1134275A3 - Copolymer blends and their use as additive to improve the cold flow properties of middle distillates - Google Patents

Copolymer blends and their use as additive to improve the cold flow properties of middle distillates Download PDF

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Publication number
EP1134275A3
EP1134275A3 EP01104848A EP01104848A EP1134275A3 EP 1134275 A3 EP1134275 A3 EP 1134275A3 EP 01104848 A EP01104848 A EP 01104848A EP 01104848 A EP01104848 A EP 01104848A EP 1134275 A3 EP1134275 A3 EP 1134275A3
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Prior art keywords
und
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alkyl
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EP01104848A
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German (de)
French (fr)
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EP1134275B1 (en
EP1134275A2 (en
Inventor
Matthias Dr. Krull
Thomas Dr. Volkmer
Werner Dr. Reimann
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Clariant Produkte Deutschland GmbH
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Clariant GmbH
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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
    • 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
    • C10L1/18—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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-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

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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Lubricants (AREA)

Abstract

Gegenstand der Erfindung sind Additive zur Verbesserung der Kaltfließeigenschaften von Mitteldestillaten, enthaltend 10 bis 95 Gew.-% Copolymere A), 5 bis 90 Gew.-% Copolymere B) und gegebenenfalls 0 bis 70 Gew.-% Copolymere C), die folgenden Formeln entsprechen

  • A) Copolymere aus niederen Olefinen und Vinylestern, enthaltend
  • A1) 85 bis 97 mol-% bivalente Struktureinheiten der Formel - CH2 - CR1R2 - worin R1 und R2 unabhängig voneinander Wasserstoff oder Methyl bedeuten, und
  • A2) mindestens 3 mol-% bivalente Struktureinheiten der Formel
    Figure 80000001
    worin R3 gesättigtes, verzweigtes C6-C16-Alkyl bedeutet, das ein tertiäres Kohlenstoffatom aufweist, dadurch gekennzeichnet, daß R3 mit seinem tertiären Kohlenstoffatom an die Carboxylfunktion gebunden ist,
  • B) Copolymere, umfassend
  • B1) 40 bis 60 mol-% bivalente Struktureinheiten der Formel
    Figure 80010001
  • mit X = O oder N - R4,
  • worin a, b = 0 oder 1 und a + b = 1 sind, und
  • B2) 60 bis 40 mol-% bivalente Struktureinheiten der Formel - H2C - CR11R5 - und gegebenenfalls
  • B3) 0 bis 20 mol-%, bivalente Struktureinheiten, die sich von Polyolefinen ableiten, wobei die Polyolefine aus Monoolefinen mit 3 bis 5 Kohlenstoffatomen ableitbar sind, und worin
  • a) R4 einen Alkyl- oder Alkenylrest mit 10 bis 40 Kohlenstoffatomen oder einen Alkoxyalkylrest mit 1 bis 100 Alkoxyeinheiten und 1 bis 30 Kohlenstoffatomen im Alkylrest, und
  • b) R5 einen Rest der Formeln OCOR12 oder COOR12 bedeutet, worin R12 für C1- bis C3-Alkyl steht, und
  • c) die Zahl der Kohlenstoffatome der den Struktureinheiten B3) zugrunde liegenden Polyolefinmoleküle zwischen 35 und 350 beträgt, und
  • d) R11 für Wasserstoff oder Methyl steht, und gegebenenfalls
  • C) ein weiteres von A) und B) verschiedenes Copolymer aus Ethylen und einem oder mehreren Vinyl- oder Acrylester, das allein Wirksamkeit als Kaltfließverbesserer für Mitteldestillate aufweist.
    • The invention relates to additives for improving the cold flow properties of middle distillates, containing 10 to 95% by weight of copolymers A), 5 to 90% by weight of copolymers B) and optionally 0 to 70% by weight of copolymers C), the following formulas correspond
  • A) containing copolymers of lower olefins and vinyl esters
  • A1) 85 to 97 mol% of bivalent structural units of the formula - CH 2 - CR 1 R 2 - wherein R 1 and R 2 are independently hydrogen or methyl, and
  • A2) at least 3 mol% of bivalent structural units of the formula
    Figure 80000001
    in which R 3 is saturated, branched C 6 -C 16 alkyl which has a tertiary carbon atom, characterized in that R 3 is bonded to the carboxyl function with its tertiary carbon atom,
  • B) Copolymers comprising
  • B1) 40 to 60 mol% of bivalent structural units of the formula
    Figure 80010001
  • with X = O or N - R 4 ,
  • wherein a, b = 0 or 1 and a + b = 1, and
  • B2) 60 to 40 mol% of bivalent structural units of the formula - H 2 C - CR 11 R 5 - and if necessary
  • B3) 0 to 20 mol%, bivalent structural units which are derived from polyolefins, the polyolefins being derivable from monoolefins having 3 to 5 carbon atoms, and in which
  • a) R 4 is an alkyl or alkenyl radical with 10 to 40 carbon atoms or an alkoxyalkyl radical with 1 to 100 alkoxy units and 1 to 30 carbon atoms in the alkyl radical, and
  • b) R 5 is a radical of the formulas OCOR 12 or COOR 12 , in which R 12 is C 1 -C 3 -alkyl, and
  • c) the number of carbon atoms of the polyolefin molecules on which the structural units B3) are based is between 35 and 350, and
  • d) R 11 represents hydrogen or methyl, and optionally
  • C) another copolymer of ethylene and one or more vinyl or acrylic esters different from A) and B), which alone has activity as a cold flow improver for middle distillates.

    • EP01104848A 2000-03-14 2001-02-28 Copolymer blends and their use as additive to improve the cold flow properties of middle distillates Expired - Lifetime EP1134275B1 (en)

    Applications Claiming Priority (2)

    Application Number Priority Date Filing Date Title
    DE10012269 2000-03-14
    DE10012269A DE10012269C2 (en) 2000-03-14 2000-03-14 Use of copolymer mixtures as an additive to improve the cold flow properties of middle distillates

    Publications (3)

    Publication Number Publication Date
    EP1134275A2 EP1134275A2 (en) 2001-09-19
    EP1134275A3 true EP1134275A3 (en) 2002-08-07
    EP1134275B1 EP1134275B1 (en) 2006-08-30

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    Application Number Title Priority Date Filing Date
    EP01104848A Expired - Lifetime EP1134275B1 (en) 2000-03-14 2001-02-28 Copolymer blends and their use as additive to improve the cold flow properties of middle distillates

    Country Status (8)

    Country Link
    US (1) US6593426B2 (en)
    EP (1) EP1134275B1 (en)
    JP (1) JP2001294875A (en)
    BR (1) BR0100313B1 (en)
    CA (1) CA2340525A1 (en)
    DE (2) DE10012269C2 (en)
    ES (1) ES2270911T3 (en)
    NO (1) NO20011255L (en)

    Families Citing this family (12)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    WO2003083840A1 (en) * 2002-03-29 2003-10-09 Fujitsu Limited Magnetic recording medium and magnetic storage apparatus
    US20040003892A1 (en) * 2002-07-08 2004-01-08 Lehman Nicholas C. One part woodworking adhesive composition
    US20040058827A1 (en) * 2002-09-24 2004-03-25 Baker Hughes Incorporated Paraffin inhibitor compositions and their use in oil and gas production
    DE10245737C5 (en) * 2002-10-01 2011-12-08 Clariant Produkte (Deutschland) Gmbh Process for the preparation of additive mixtures for mineral oils and mineral oil distillates
    US7541315B2 (en) * 2003-09-11 2009-06-02 Baker Hughes Incorporated Paraffin inhibitor compositions and their use in oil and gas production
    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
    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
    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
    EP1555310A1 (en) * 2003-12-16 2005-07-20 Infineum International Limited Cold flow improver compositions for fuels
    WO2006105306A2 (en) * 2005-03-29 2006-10-05 Arizona Chemical Company Compostions containing fatty acids and/or derivatives thereof and a low temperature stabilizer

    Citations (6)

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    EP0153176A2 (en) * 1984-02-21 1985-08-28 Exxon Research And Engineering Company Middle distillate compositions with improved cold flow properties
    EP0154177A2 (en) * 1984-02-17 1985-09-11 Bayer Ag Copolymers based on maleic anhydride and alpha-, beta-unsaturated compounds, process for their manufacture and their use as paraffin inhibitors
    EP0807642A1 (en) * 1996-05-18 1997-11-19 Hoechst Aktiengesellschaft Ethylene terpolymers, their preparation and their use as additives for mineral oil distillates
    EP0890589A2 (en) * 1997-07-08 1999-01-13 Clariant GmbH Copolymers, based on olefins and unsaturated carboxylic esters and their use as additives for mineral oils
    EP0890633A1 (en) * 1997-07-08 1999-01-13 Clariant GmbH Middle distillates and ethylene and unsaturated carboxylic esters copolymers containing fuel oils
    EP0931824A2 (en) * 1998-01-24 1999-07-28 Clariant GmbH Process to improve the cold flow properties of fuel oils

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    US3048479A (en) 1959-08-03 1962-08-07 Exxon Research Engineering Co Ethylene-vinyl ester pour depressant for middle distillates
    NL265065A (en) 1961-05-23
    DE1914756C3 (en) 1968-04-01 1985-05-15 Exxon Research and Engineering Co., Linden, N.J. Use of ethylene-vinyl acetate copolymers for petroleum distillates
    US3966428A (en) 1973-10-31 1976-06-29 Exxon Research And Engineering Company Ethylene backbone polymers in combination with ester polymers having long alkyl side chains are low viscosity distillate fuel cold flow improvers
    DE3514878A1 (en) 1985-04-25 1986-11-06 Henkel KGaA, 4000 Düsseldorf Oil-soluble esters of copolymers of maleic anhydride
    GB8521393D0 (en) 1985-08-28 1985-10-02 Exxon Chemical Patents Inc Middle distillate compositions
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    Patent Citations (6)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    EP0154177A2 (en) * 1984-02-17 1985-09-11 Bayer Ag Copolymers based on maleic anhydride and alpha-, beta-unsaturated compounds, process for their manufacture and their use as paraffin inhibitors
    EP0153176A2 (en) * 1984-02-21 1985-08-28 Exxon Research And Engineering Company Middle distillate compositions with improved cold flow properties
    EP0807642A1 (en) * 1996-05-18 1997-11-19 Hoechst Aktiengesellschaft Ethylene terpolymers, their preparation and their use as additives for mineral oil distillates
    EP0890589A2 (en) * 1997-07-08 1999-01-13 Clariant GmbH Copolymers, based on olefins and unsaturated carboxylic esters and their use as additives for mineral oils
    EP0890633A1 (en) * 1997-07-08 1999-01-13 Clariant GmbH Middle distillates and ethylene and unsaturated carboxylic esters copolymers containing fuel oils
    EP0931824A2 (en) * 1998-01-24 1999-07-28 Clariant GmbH Process to improve the cold flow properties of fuel oils

    Also Published As

    Publication number Publication date
    DE50110842D1 (en) 2006-10-12
    ES2270911T3 (en) 2007-04-16
    DE10012269C2 (en) 2003-05-15
    JP2001294875A (en) 2001-10-23
    DE10012269A1 (en) 2001-10-11
    US6593426B2 (en) 2003-07-15
    EP1134275B1 (en) 2006-08-30
    NO20011255D0 (en) 2001-03-13
    EP1134275A2 (en) 2001-09-19
    BR0100313A (en) 2001-11-06
    CA2340525A1 (en) 2001-09-14
    BR0100313B1 (en) 2011-09-20
    NO20011255L (en) 2001-09-17
    US20010034410A1 (en) 2001-10-25

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