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EP1146108A3 - 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
EP1146108A3
EP1146108A3 EP01104847A EP01104847A EP1146108A3 EP 1146108 A3 EP1146108 A3 EP 1146108A3 EP 01104847 A EP01104847 A EP 01104847A EP 01104847 A EP01104847 A EP 01104847A EP 1146108 A3 EP1146108 A3 EP 1146108A3
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bis
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EP01104847A
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German (de)
French (fr)
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EP1146108B1 (en
EP1146108A2 (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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    • 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
    • C10L1/196—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
    • C10L1/18—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

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)

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 80000002
  • mit X = O oder N - R4,
  • worin a, b = 0 oder 1 und a + b = 1 sind, und
  • B2) 35 bis 53 mol-% bivalente Struktureinheiten der Formel - H2C - CHR5 - 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 Alkylrest mit 10 bis 50 Kohlenstoffatomen bedeutet, und
  • c) die Zahl der Kohlenstoffatome der den Struktureinheiten B3) zugrunde liegenden Polyolefinmoleküle zwischen 35 und 350 beträgt, 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 80000002
  • with X = O or N - R 4 ,
  • wherein a, b = 0 or 1 and a + b = 1, and
  • B2) 35 to 53 mol% of bivalent structural units of the formula - H 2 C - CHR 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 an alkyl radical having 10 to 50 carbon atoms, 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 if appropriate
  • 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.

    • EP01104847A 2000-03-14 2001-02-28 Copolymer blends and their use as additive to improve the cold flow properties of middle distillates Expired - Lifetime EP1146108B1 (en)

    Applications Claiming Priority (2)

    Application Number Priority Date Filing Date Title
    DE10012267A DE10012267B4 (en) 2000-03-14 2000-03-14 Copolymer blends and their use as an additive to improve the cold flow properties of middle distillates
    DE10012267 2000-03-14

    Publications (3)

    Publication Number Publication Date
    EP1146108A2 EP1146108A2 (en) 2001-10-17
    EP1146108A3 true EP1146108A3 (en) 2002-08-07
    EP1146108B1 EP1146108B1 (en) 2006-09-20

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    Application Number Title Priority Date Filing Date
    EP01104847A Expired - Lifetime EP1146108B1 (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 (9)

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    US (1) US6565616B1 (en)
    EP (1) EP1146108B1 (en)
    JP (1) JP2001288484A (en)
    BR (1) BR0100233B1 (en)
    CA (1) CA2340524A1 (en)
    DE (2) DE10012267B4 (en)
    ES (1) ES2272366T3 (en)
    NO (1) NO20011254L (en)
    PT (1) PT1146108E (en)

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    JP4768956B2 (en) * 2002-07-09 2011-09-07 クラリアント・プロドゥクテ・（ドイチュラント）・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング Cold fluidity improver for fuel oils of plant or animal origin
    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
    JP2004193756A (en) * 2002-12-09 2004-07-08 Canon Inc Electronic watermark embedding method
    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
    US7326453B2 (en) * 2004-02-04 2008-02-05 3M Innovative Properties Company Article with selectively activated adhesive
    DE102006016588A1 (en) * 2006-04-06 2007-10-18 Rohmax Additives Gmbh Fuel compositions comprising renewable resources
    DE102006022720B4 (en) * 2006-05-16 2008-10-02 Clariant International Limited Cold flow improver for vegetable or animal fuel oils
    DE102006033151B4 (en) 2006-07-18 2014-11-20 Clariant International Limited Additives for improving the cold properties of fuel oils
    DE102006033149A1 (en) * 2006-07-18 2008-01-31 Clariant International Limited Additives for improving the cold properties of fuel oils
    DE102006033150B4 (en) * 2006-07-18 2008-10-16 Clariant International Limited Additives for improving the cold properties of fuel oils
    ATE547472T1 (en) 2009-09-25 2012-03-15 Evonik Rohmax Additives Gmbh COMPOSITION FOR IMPROVING THE COLD FLOW PROPERTIES OF FUEL OILS
    EP2535396B1 (en) 2010-02-10 2017-04-19 NOF Corporation Method with fluidity improver for fats and vegetable oils
    JP5634302B2 (en) * 2011-02-28 2014-12-03 株式会社Adeka Low temperature fluidity improver for fatty acid methyl esters
    CN103370400B (en) 2011-03-25 2016-12-14 赢创油品添加剂有限公司 For improving the compositions of fuel oil oxidation stability
    CN103635498B (en) * 2011-11-23 2016-03-02 深圳市广昌达石油添加剂有限公司 A kind of multipolymer for Copolymer As Diesel Fuel Cold Flow Improver and synthetic method thereof
    US20130212931A1 (en) * 2012-02-16 2013-08-22 Baker Hughes Incorporated Biofuel having improved cold flow properties
    JP2015528523A (en) 2012-09-13 2015-09-28 エボニック オイル アディティヴス ゲゼルシャフト ミット ベシュレンクテル ハフツングＥｖｏｎｉｋ Ｏｉｌ Ａｄｄｉｔｉｖｅｓ ＧｍｂＨ Composition for improving low temperature properties and oxidative stability of vegetable oils and animal fats
    WO2014118370A1 (en) 2013-02-04 2014-08-07 Evonik Industries Ag Cold flow improver with broad applicability in mineral diesel, biodiesel and blends thereof
    CN104830387B (en) * 2015-05-29 2016-05-04 马健 A kind of diesel oil antifreezing agent that reduces discharging

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    EP0214786A1 (en) * 1985-08-28 1987-03-18 Exxon Chemical Patents Inc. Middle distillate compositions with improved low temperature properties
    EP0320766A2 (en) * 1987-12-16 1989-06-21 Hoechst Aktiengesellschaft Viscosity index-modifying polymer blends for petroleum fractions
    EP0807642A1 (en) * 1996-05-18 1997-11-19 Hoechst Aktiengesellschaft Ethylene terpolymers, their preparation and their use as additives for mineral oil distillates
    EP0890633A1 (en) * 1997-07-08 1999-01-13 Clariant GmbH Middle distillates and ethylene and unsaturated carboxylic esters copolymers containing fuel oils
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    Also Published As

    Publication number Publication date
    PT1146108E (en) 2007-01-31
    JP2001288484A (en) 2001-10-16
    DE50111031D1 (en) 2006-11-02
    DE10012267B4 (en) 2005-12-15
    EP1146108B1 (en) 2006-09-20
    BR0100233B1 (en) 2011-05-03
    US6565616B1 (en) 2003-05-20
    EP1146108A2 (en) 2001-10-17
    NO20011254D0 (en) 2001-03-13
    CA2340524A1 (en) 2001-09-14
    ES2272366T3 (en) 2007-05-01
    BR0100233A (en) 2001-11-06
    DE10012267A1 (en) 2001-10-11
    NO20011254L (en) 2001-09-17

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