EP1380635A3 - Cold flow improver for fuel oils of vegetable or animal origin. - Google Patents

Cold flow improver for fuel oils of vegetable or animal origin. Download PDF

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Publication number
EP1380635A3
EP1380635A3 EP03013091A EP03013091A EP1380635A3 EP 1380635 A3 EP1380635 A3 EP 1380635A3 EP 03013091 A EP03013091 A EP 03013091A EP 03013091 A EP03013091 A EP 03013091A EP 1380635 A3 EP1380635 A3 EP 1380635A3
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EP
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Prior art keywords
und
der
den
hand
olefins
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EP03013091A
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German (de)
French (fr)
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EP1380635B1 (en
EP1380635A2 (en
Inventor
Matthias Dr. Krull
Bettina Dr. Siggelkow
Martina Hess
Ulrike Neuhaus
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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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
    • 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
    • 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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1835—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom having at least two hydroxy substituted non condensed benzene rings
    • 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
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • 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
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
    • 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
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1981—Condensation polymers of aldehydes or ketones
    • 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
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/022—Ethene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/013—Iodine value
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/067—Unsaturated Compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/40—Low content or no content compositions
    • C10N2030/43—Sulfur free or low sulfur content compositions

Abstract

Gegenstand der Erfindung ist ein Additiv, enthaltend

  • A) ein Copolymer aus Ethylen und 8 - 21 Mol-% mindestens eines Acryl- oder Vinylesters mit einem C1-C18-Alkylrest und
  • B) ein Kammpolymer aus mindestens einem C8-C16-Alkylester einer ethylenisch ungesättigten Dicarbonsäure und mindestens einem C10-C20-Olefin, wobei die Summe Q
    Figure 80000001
    • der molaren Mittel der C-Kettenverteilungen in den Alkylseitenketten der Olefine einerseits und den Fettalkoholen in den Estergruppen andererseits von 23 bis 27 beträgt, wobei w1 und w2 die molaren Anteile der einzelnen Kettenlängen in den Alkylseitenketten der Olefine einerseits und den Fettalkoholen in den Estergruppen andererseits sind und n1 und n2 für die Seitenkettenlängen, bei Olefinen ohne die ursprünglich olefinisch gebundenen C-Atome, der Alkylseitenketten der Olefine einerseits und der Fettalkohole in den Estergruppen andererseits stehen, und die Laufvariablen i und j für die einzelnen Seitenkettenlängen in den Alkylseitenketten der Olefine einerseits und der Fettalkohole in den Estergruppen andererseits stehen.The invention relates to an additive containing
  • A) a copolymer of ethylene and 8 to 21 mol% of at least one acrylic or vinyl ester having a C 1 -C 18 -alkyl radical and
  • B) a comb polymer of at least one C 8 -C 16 alkyl ester of an ethylenically unsaturated dicarboxylic acid and at least one C 10 -C 20 olefin, wherein the sum Q
    Figure 80000001
    •  the molar average of the C chain distributions in the alkyl side chains of the olefins on the one hand and the fatty alcohols in the ester groups on the other hand from 23 to 27, wherein w 1 and w 2, the molar ratios of the individual chain lengths in the alkyl side chains of the olefins on the one hand and the fatty alcohols in the ester groups On the other hand, and n 1 and n 2 are the side chain lengths, olefins without the originally olefinically bonded C atoms, the alkyl side chains of the olefins on the one hand and the fatty alcohols in the ester groups on the other hand, and the run variables i and j for the individual side chain lengths in the alkyl side chains the olefins on the one hand and the fatty alcohols in the ester groups on the other hand.

    EP03013091A 2002-07-09 2003-06-11 Cold flow improver for fuel oils of vegetable or animal origin. Expired - Lifetime EP1380635B1 (en)

    Applications Claiming Priority (2)

    Application Number Priority Date Filing Date Title
    DE10230771 2002-07-09
    DE10230771 2002-07-09

    Publications (3)

    Publication Number Publication Date
    EP1380635A2 EP1380635A2 (en) 2004-01-14
    EP1380635A3 true EP1380635A3 (en) 2004-03-10
    EP1380635B1 EP1380635B1 (en) 2013-01-23

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    ID=29723798

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    EP03013091A Expired - Lifetime EP1380635B1 (en) 2002-07-09 2003-06-11 Cold flow improver for fuel oils of vegetable or animal origin.

    Country Status (6)

    Country Link
    US (1) US7041738B2 (en)
    EP (1) EP1380635B1 (en)
    JP (1) JP4768956B2 (en)
    KR (1) KR100990625B1 (en)
    CA (1) CA2431746C (en)
    ES (1) ES2399626T3 (en)

    Families Citing this family (39)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    CA2431748C (en) * 2002-07-09 2010-11-09 Clariant Gmbh Oxidation-stabilized oily liquids based on vegetable or animal oils
    JP4484458B2 (en) * 2002-07-09 2010-06-16 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 Oxidation-stable lubricant additive for highly desulfurized fuel oil
    PL1491614T3 (en) * 2003-06-23 2012-09-28 Infineum Int Ltd Oil compositions
    DE10349851B4 (en) * 2003-10-25 2008-06-19 Clariant Produkte (Deutschland) Gmbh Cold flow improver for 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
    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
    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
    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
    US20050138859A1 (en) * 2003-12-16 2005-06-30 Graham Jackson Cold flow improver compositions for fuels
    US9051527B2 (en) * 2005-02-11 2015-06-09 Infineum International Limited Fuel oil compositions
    CA2602220C (en) 2005-03-29 2013-12-17 Arizona Chemical Company Compostions containing fatty acids and/or derivatives thereof and a low temperature stabilizer
    US20060236598A1 (en) * 2005-04-26 2006-10-26 Flint Hills Resources, L.P. Low temperature biodiesel diesel blend
    MY142383A (en) * 2005-06-10 2010-11-30 Malaysian Palm Oil Board Mpob Palm- based biodiesel formulation
    DE102005045133B4 (en) * 2005-09-22 2008-07-03 Clariant Produkte (Deutschland) Gmbh Additives for crude oils
    DE102005045134B4 (en) * 2005-09-22 2010-12-30 Clariant Produkte (Deutschland) Gmbh Alkylphenol-aldehyde resins, compositions containing them for improving the low-flowability and lubricity of fuel oils and their use
    DE102006022698B4 (en) * 2006-05-16 2008-10-02 Clariant International Limited Composition of fuel oils
    DE102006022719B4 (en) * 2006-05-16 2008-10-02 Clariant International Limited Cold flow improver for vegetable or animal fuel oils
    DE102006022718B4 (en) * 2006-05-16 2008-10-02 Clariant International Limited Composition of fuel oils
    BRPI0713072A2 (en) * 2006-06-30 2012-07-17 Univ North Dakota method for producing a fuel composition, and, fuel composition
    FR2903418B1 (en) * 2006-07-10 2012-09-28 Total France USE OF COMPOUNDS REVELATING THE EFFICACY OF FILTRABILITY ADDITIVES IN HYDROCARBON DISTILLATES, AND SYNERGIC COMPOSITION CONTAINING THEM.
    US7655055B2 (en) * 2006-09-21 2010-02-02 Southwest Research Institute Biofuel
    EP1992674A1 (en) * 2007-05-08 2008-11-19 Shell Internationale Researchmaatschappij B.V. Diesel fuel compositions comprising a gas oil base fuel, a fatty acid alkyl ester and an aromatic component
    EP2152835B1 (en) * 2007-05-08 2019-04-03 Shell International Research Maatschappij B.V. Use of a fatty acid alkyl ester in diesel fuel compositions comprising a gas oil base fuel
    WO2008154558A2 (en) * 2007-06-11 2008-12-18 Arkema Inc. Acrylic polymer low temperature flow modifiers in bio-derived fuels
    EP2036962A1 (en) * 2007-09-14 2009-03-18 Cognis Oleochemicals GmbH Additives for water-based drilling fluids
    EP2036963A1 (en) * 2007-09-14 2009-03-18 Cognis Oleochemicals GmbH Lubricants for drilling fluids
    EP2036964A1 (en) * 2007-09-14 2009-03-18 Cognis Oleochemicals GmbH Thickener for oil-based drilling fluids
    US8076504B2 (en) * 2007-12-31 2011-12-13 The University Of North Dakota Method for production of short chain carboxylic acids and esters from biomass and product of same
    US20100109245A1 (en) * 2008-10-30 2010-05-06 Double-Back Jack, Llc Method of playing a variation of blackjack (21)
    AU2009320371B2 (en) * 2008-11-26 2015-09-17 University Of North Dakota Method for producing cyclic organic compounds from crop oils
    JP5662424B2 (en) * 2009-05-14 2015-01-28 ユニヴァーシティー オブ ノースダコタ Process for producing high carbon content products from biomass oil
    EP2699533A4 (en) 2011-04-22 2015-03-04 Univ North Dakota Production of aromatics from noncatalytically cracked fatty acid based oils
    US20130212931A1 (en) * 2012-02-16 2013-08-22 Baker Hughes Incorporated Biofuel having improved cold flow properties
    US10557335B2 (en) 2014-01-24 2020-02-11 Schlumberger Technology Corporation Gas fracturing method and system
    CA3009228C (en) 2017-12-19 2019-06-11 Exxonmobil Research And Engineering Company Dewaxed diesel fuel composition
    WO2019133659A1 (en) * 2017-12-28 2019-07-04 Ecolab Usa Inc. Cloud point depressant for middle distillate fuels
    CN108456593A (en) * 2018-04-08 2018-08-28 福建鑫绿林产品开发有限公司 A kind of fir essential oil production fuel adding method
    WO2020014189A1 (en) 2018-07-11 2020-01-16 Ecolab Usa Inc. Cold flow additive for middle distillate fuels
    US20230120367A1 (en) * 2021-10-14 2023-04-20 Ecolab Usa Inc. Antifouling agents for plastic-derived synthetic feedstocks

    Citations (8)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    GB907177A (en) * 1959-09-22 1962-10-03 Socony Mobil Oil Co Inc Stabilized jet combustion fuels
    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
    EP0214786A1 (en) * 1985-08-28 1987-03-18 Exxon Chemical Patents Inc. Middle distillate compositions with improved low temperature properties
    US4652611A (en) * 1982-04-12 1987-03-24 Mitsubishi Chemical Industries Limited Low-temperature fluidity improver
    EP0282342A1 (en) * 1987-03-12 1988-09-14 Exxon Chemical Patents Inc. Fuel compositions
    WO1993018115A1 (en) * 1992-03-03 1993-09-16 Exxon Chemical Patents Inc. Additives for oils
    WO1994010267A1 (en) * 1992-10-26 1994-05-11 Exxon Chemical Patents Inc. Oil additives and compositions
    EP1146108A2 (en) * 2000-03-14 2001-10-17 Clariant GmbH Copolymer blends and their use as additive to improve the cold flow properties of middle distillates

    Family Cites Families (39)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    US2499365A (en) 1947-03-07 1950-03-07 Petrolite Corp Chemical manufacture
    NL130122C (en) 1962-05-01
    GB2095698A (en) 1981-03-31 1982-10-06 Exxon Research Engineering Co Two-component flow improver for middle 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
    IN168191B (en) 1984-02-21 1991-02-16 Exxon Research Engineering Co
    DE3443475A1 (en) 1984-11-29 1986-05-28 Amoco Corp., Chicago, Ill. TERPOLYMERISATE OF ETHYLENE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE
    DE3616056A1 (en) 1985-05-29 1986-12-04 Hoechst Ag, 65929 Frankfurt USE OF ETHYLENE TERPOLYMERISATES AS ADDITIVES FOR MINERAL OILS AND MINERAL OIL DISTILLATES
    DE3625174A1 (en) 1986-07-25 1988-01-28 Ruhrchemie Ag METHOD FOR IMPROVING THE FLOWABILITY OF MINERAL OILS AND MINERAL OIL DISTILLATES
    DE3640613A1 (en) 1986-11-27 1988-06-09 Ruhrchemie Ag METHOD FOR THE PRODUCTION OF ETHYLENE MIXED POLYMERISATES AND THE USE THEREOF AS AN ADDITION TO MINERAL OIL AND MINERAL OIL FRACTIONS
    DE3742630A1 (en) 1987-12-16 1989-06-29 Hoechst Ag POLYMER BLENDS FOR IMPROVING THE FLOWABILITY OF MINERAL OIL DISTILLATES IN THE COLD
    DE3916366A1 (en) 1989-05-19 1990-11-22 Basf Ag NEW IMPLEMENTATION PRODUCTS OF AMINOALKYLENE POLYCARBONIC ACIDS WITH SECOND AMINES AND PETROLEUM DISTILLATE COMPOSITIONS THAT CONTAIN THEM
    DE3921279A1 (en) 1989-06-29 1991-01-03 Hoechst Ag METHOD FOR IMPROVING THE FLOWABILITY OF MINERAL OILS AND MINERAL OIL DISTILLATES
    DE3926992A1 (en) 1989-08-16 1991-02-21 Hoechst Ag USE OF TRANSPARENT PRODUCTS OF ALKENYL SPIROBISLACTONES AND AMINES AS PARAFFINDISPERGATORS
    GB9007970D0 (en) * 1990-04-09 1990-06-06 Exxon Chemical Patents Inc Fuel oil compositions
    DE4020640A1 (en) 1990-06-29 1992-01-02 Hoechst Ag TERPOLYMERISATES OF ETHYLENE, THEIR PRODUCTION AND THEIR USE AS ADDITIVES FOR MINERAL OIL DISTILLATES
    DE4040317A1 (en) 1990-12-17 1992-06-25 Henkel Kgaa MIXTURES OF FATTY ACID LOW ALKYL ESTERS WITH IMPROVED COLD TESTABILITY
    DE4042206A1 (en) 1990-12-29 1992-07-02 Hoechst Ag ETHYLENE TERPOLYMERISES, THEIR PREPARATION AND THEIR USE AS ADDITIVES FOR MINERALOLE DISTILLATES
    DE4138429A1 (en) 1991-11-22 1993-05-27 Roehm Gmbh METHOD FOR PRODUCING COMPOSITIONS WITH IMPROVED LOW TEMPERATURE BEHAVIOR
    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
    IT1270954B (en) 1993-07-21 1997-05-26 Euron Spa DIESEL COMPOSITION
    DE4422159A1 (en) 1994-06-24 1996-01-04 Hoechst Ag Reaction products of polyetheramines with polymers alpha, beta-unsaturated dicarboxylic acids
    CZ60097A3 (en) 1994-08-30 1997-07-16 Procter & Gamble Chelating agents increasing photobleaching
    GB9417670D0 (en) * 1994-09-02 1994-10-19 Exxon Chemical Patents Inc Oil additives, compositions and polymers for use therein
    MX9703154A (en) * 1994-10-28 1998-02-28 Procter & Gamble Hard surface cleaning compositions comprising protonated amines and amine oxide surfactants.
    GB9514480D0 (en) 1995-07-14 1995-09-13 Exxon Chemical Patents Inc Additives and fuel oil compositions
    DE69518404T2 (en) 1994-12-13 2001-01-25 Infineum Usa Lp OIL FUEL COMPOSITIONS COMPREHENSIVE OIL FUELS BASED ON PETROLEUM, ETHYLENE-UNSATURATED ESTER COPOLYMERS AND ESTERS OF MULTI-VALUE ALCOHOLS WITH CARBONIC ACIDS
    JP3379866B2 (en) 1995-04-24 2003-02-24 花王株式会社 Gas oil additive and gas oil composition
    DE19614722A1 (en) 1996-04-15 1997-10-16 Henkel Kgaa Low-temperature lubricant and fuel additive
    DE19620119C1 (en) 1996-05-18 1997-10-23 Hoechst Ag Terpolymers of ethylene, their production and their use as additives for mineral oil distillates
    DE19620118C1 (en) 1996-05-18 1997-10-23 Hoechst Ag Terpolymers of ethylene, their preparation and their use as additives for mineral oil distillates
    GB9621231D0 (en) 1996-10-11 1996-11-27 Exxon Chemical Patents Inc Low sulfer fuels with lubricity additive
    GB9707367D0 (en) * 1997-04-11 1997-05-28 Exxon Chemical Patents Inc Improved oil compositions
    GB9810994D0 (en) 1998-05-22 1998-07-22 Exxon Chemical Patents Inc Additives and oil compositions
    EP1088880A1 (en) 1999-09-10 2001-04-04 Fina Research S.A. Fuel composition
    AU1290501A (en) * 1999-11-23 2001-06-04 Associated Octel Company Limited, The Composition
    GB0009310D0 (en) * 2000-04-17 2000-05-31 Infineum Int Ltd Fuel oil compositions
    DE10058357B4 (en) * 2000-11-24 2005-12-15 Clariant Gmbh Fatty acid mixtures of improved cold stability, which contain comb polymers, as well as their use in fuel oils
    DE10111857A1 (en) 2001-03-08 2002-09-12 Wolfram Radig Multifunctional additive, for desulfurized mineral diesel fuel, comprises saturated fatty acid esters of lower alcohols and methylated dihydroxybenzenes

    Patent Citations (8)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    GB907177A (en) * 1959-09-22 1962-10-03 Socony Mobil Oil Co Inc Stabilized jet combustion fuels
    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
    US4652611A (en) * 1982-04-12 1987-03-24 Mitsubishi Chemical Industries Limited Low-temperature fluidity improver
    EP0214786A1 (en) * 1985-08-28 1987-03-18 Exxon Chemical Patents Inc. Middle distillate compositions with improved low temperature properties
    EP0282342A1 (en) * 1987-03-12 1988-09-14 Exxon Chemical Patents Inc. Fuel compositions
    WO1993018115A1 (en) * 1992-03-03 1993-09-16 Exxon Chemical Patents Inc. Additives for oils
    WO1994010267A1 (en) * 1992-10-26 1994-05-11 Exxon Chemical Patents Inc. Oil additives and compositions
    EP1146108A2 (en) * 2000-03-14 2001-10-17 Clariant GmbH Copolymer blends and their use as additive to improve the cold flow properties of middle distillates

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    CA2431746A1 (en) 2004-01-09
    KR20040005587A (en) 2004-01-16
    JP2004043799A (en) 2004-02-12
    US20040010072A1 (en) 2004-01-15
    JP4768956B2 (en) 2011-09-07
    EP1380635A2 (en) 2004-01-14
    ES2399626T3 (en) 2013-04-02
    CA2431746C (en) 2011-11-01
    KR100990625B1 (en) 2010-10-29
    US7041738B2 (en) 2006-05-09

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