EP1209215B1 - Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant - Google Patents

Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant Download PDF

Info

Publication number
EP1209215B1
EP1209215B1 EP01126254A EP01126254A EP1209215B1 EP 1209215 B1 EP1209215 B1 EP 1209215B1 EP 01126254 A EP01126254 A EP 01126254A EP 01126254 A EP01126254 A EP 01126254A EP 1209215 B1 EP1209215 B1 EP 1209215B1
Authority
EP
European Patent Office
Prior art keywords
weight
alkyl
structural units
formula
mol
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.)
Expired - Lifetime
Application number
EP01126254A
Other languages
German (de)
English (en)
Other versions
EP1209215A2 (fr
EP1209215A3 (fr
Inventor
Matthias Dr. Krull
Werner Dr. Reimann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant Produkte Deutschland GmbH
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=7664508&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP1209215(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Clariant Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Priority to EP07005871A priority Critical patent/EP1801188B1/fr
Priority to EP07005870A priority patent/EP1803791B1/fr
Publication of EP1209215A2 publication Critical patent/EP1209215A2/fr
Publication of EP1209215A3 publication Critical patent/EP1209215A3/fr
Application granted granted Critical
Publication of EP1209215B1 publication Critical patent/EP1209215B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C10L1/143—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
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • 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
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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
    • C10L1/16—Hydrocarbons
    • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
    • 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
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • 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
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
    • 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
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • 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
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C10L1/1883—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
    • 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
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1885—Carboxylic acids; metal salts thereof resin acid
    • 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
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1888—Carboxylic acids; metal salts thereof tall oil
    • 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
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • 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
    • C10L1/198—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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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
    • 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
    • C10L1/238—Macromolecular compounds obtained otherwise than 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • the present invention relates to mixtures of fatty acids and paraffin dispersants having improved low-temperature stability, and to their use for improving the lubricity of middle distillate fuel oils.
  • Mineral oils and mineral oil distillates used as fuel oils generally contain 0.5% by weight and more sulfur which causes the formation of sulfur dioxide upon combustion. In order to reduce the resulting environmental impact, the sulfur content of fuel oils is lowered further and further.
  • the standard EN 590 relating to diesel fuels currently prescribes a maximum sulfur content of 350 ppm in Germany. In Scandinavia fuel oils of less than 50 ppm and in exceptional cases less than 10 ppm of sulfur are used. These fuel oils are usually prepared by hydrogenating the fractions obtained from the petroleum by distillation. In the desulfurization but other substances are removed, which give the fuel oils a natural lubricating effect. These substances include polyaromatic and polar compounds.
  • EP-A-0 798 364 discloses salts and amides of mono- to tetracarboxylic acids having 2 to 50 carbon atoms and aliphatic mono- / polyamines having 2 to 50 carbon atoms and 1 to 10 N atoms as lubricity additives for low-sulfur diesel fuel.
  • Preferred amines have 8-20 C-atoms, such as coco fatty amine, tallow fatty amine and oleylamine.
  • WO 95/33805 discloses the use of cold flow improvers to improve the lubricity of low sulfur middle distillates.
  • polar nitrogen-containing compounds which contain a group NR 13 , where R 13 is a hydrocarbon radical having 8 to 40 C atoms and may be present in the form of a cation.
  • WO-A-96/18706 disclosed in analogy to WO 95/33805 the use of the nitrogen-containing compounds mentioned therein in combination with lubricity additives.
  • WO-A-96/23855 disclosed in analogy to WO 95/33805 the use of the nitrogen-containing compounds mentioned therein in combination with detergent additives.
  • the fatty acids used in the prior art have the disadvantage that they solidify when stored at low temperatures, ie often at room temperature, usually at temperatures of 0 ° C at -5 ° C at the latest, or that deposit crystalline particles and problems prepare handling. This problem can only be partially solved by dilution with organic solvents, since components also crystallize out of these solutions or the solution gels and solidifies. For use as lubricity additives, they therefore have to be diluted considerably, or kept in heated storage containers and metered via heated lines.
  • the object underlying the present invention was to find lubricity additives which improve the lubricating effect of middle distillates at reduced metering rates, but remain homogeneous, clear and, in particular, free-flowing even in the cold.
  • Another object of the invention are cold-stabilized solutions of the additives of the invention in organic solvents, wherein the solutions contain 1 to 80 wt .-% of solvent.
  • Suitable solvents are aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures.
  • the additives according to the invention preferably contain from 10 to 70%, in particular from 25 to 60% of solvent.
  • the cold-stabilized solutions according to the invention have a pour point of below -40 ° C., preferably -45 ° C., especially -50 ° C.
  • Another object of the invention is the use of said mixtures of the components A and B to improve the lubricating properties of low-sulfur middle distillates with up to 0.05 wt .-% sulfur content.
  • Preferred fatty acids are those having 8-40 C atoms, in particular 12-22 C atoms.
  • the alkyl radicals of the fatty acids consist essentially of carbon and hydrogen. However, they may contain other substituents, e.g. Hydroxyl, halogen, amino or nitro groups, provided they do not affect the predominantly hydrocarbon character.
  • Component A2) may contain one or more double bonds and be of natural or synthetic origin. In the case of polyunsaturated carboxylic acids, their double bonds may be isolated or else conjugated.
  • the proportion of saturated fatty acids A1) in the mixture of A1) and A2) is preferably below 20% by weight, in particular below 10% by weight, especially below 5% by weight.
  • preferred fatty acid mixtures, which here the combination of A1) and A2) understood is at least 50 wt .-%, in particular at least 75 wt .-%, especially at least 90 wt .-% of the constituents one or more double bonds.
  • These preferred fatty acid (mixtures) have iodine numbers of at least 40 gl / 100 g, preferably at least 80 gl / 100 g, in particular at least 125 gl / 100 g.
  • Suitable fatty acids are, for example, lauric, tridecane, myristic, pentadecane, palmitic, margarine, stearic, isostearic, arachic and behenic acid, oleic and erucic acid, palmitoleic, myristoleic, linoleic, linolenic, elaeosterol - And arachidonic acid, ricinoleic acid and derived from natural fats and oils fatty acid mixtures, such as Coconut oil, peanut oil, fish, linseed oil, palm oil, rapeseed oil, ricinine, castor oil, rapeseed oil, soybean oil, sunflower oil and tall oil fatty acid.
  • dicarboxylic acids such as dimer fatty acids and alkyl- and alkenylsuccinic acids with C 8 -C 50 -alk (en) yl radicals, preferably with C 8 -C 40 -, in particular with C 12 -C 22 -alkyl radicals.
  • the alkyl radicals can be linear or branched (oligomerized alkenes, PIB).
  • the fatty acids may further contain 1-40, especially 1-25% by weight of resin acids, based on the weight of A1) and A2) together.
  • the additives according to the invention contain as component B at least one polar nitrogen-containing compound which is effective as paraffin dispersant in middle distillates.
  • Paraffin dispersants reduce the size of paraffin crystals precipitated in the cold and cause the paraffin particles not to settle but to remain colloidally dispersed with significantly reduced sedimentation effort.
  • alkyl, cycloalkyl and aryl radicals may optionally be substituted.
  • Suitable substituents of the alkyl and aryl radicals are, for example, (C 1 -C 6 ) -alkyl, halogens, such as fluorine, chlorine, bromine and iodine, preferably chlorine and (C 1 -C 6 ) -alkoxy.
  • Alkyl here stands for a straight-chain or branched hydrocarbon radical. Specific examples which may be mentioned are: n-butyl, tert-butyl, n-hexyl, n-octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, dodecenyl, tetrapropenyl, tetradecenyl, pentapropenyl, hexadecenyl, octadecenyl and eicosanyl or mixtures such as cocoalkyl , Tallow fatty alkyl and behenyl.
  • Cycloalkyl here stands for a cyclic aliphatic radical with 5-20 Carbon atoms.
  • Preferred cycloalkyl radicals are cyclopentyl and cyclohexyl.
  • Aryl here stands for an optionally substituted aromatic ring system having 6 to 18 carbon atoms.
  • the terpolymers consist of the bivalent structural units of the formulas 12 and 14 and 15 and 16 and optionally 13. They contain only in a conventional manner the end groups formed in the polymerization by initiation, inhibition and chain termination.
  • structural units of the formulas 12 to 14 are derived from ⁇ , ⁇ -unsaturated dicarboxylic acid anhydrides of the formulas 17 and 18 such as maleic anhydride, itaconic anhydride, citraconic anhydride, preferably maleic anhydride.
  • the structural units of the formula 15 are derived from the ⁇ , ⁇ -unsaturated compounds of the formula 19.
  • the structural units of formula 16 are derived from polyoxyalkylene ethers of lower, unsaturated alcohols of formula 20.
  • ⁇ -olefin oxides such as ethylene oxide, propylene oxide and / or butylene oxide
  • polymerizable lower unsaturated alcohols are, for example, allyl alcohol, methallyl alcohol, butenols, such as 3-buten-1-ol and 1-buten-3-ol or methylbutenols, such as 2-methyl-3-buten-1-ol, 2-methyl-3 -but-2-ol and 3-methyl-3-buten-1-ol.
  • Preferred are addition products of ethylene oxide and / or propylene oxide with allyl alcohol.
  • etherification products of the polyoxyalkylene ethers can also be prepared by reacting ⁇ -olefin oxides, preferably ethylene oxide, propylene oxide and / or butylene oxide, with alcohols of the formula 22 R 32 - OH (22) wherein R 32 is equal to C 1 -C 24 alkyl, C 5 -C 20 cycloalkyl or C 6 -C 18 aryl, by known methods attached and with polymerizable lower unsaturated halides of the formula 23rd where W is a halogen atom.
  • the halides used are preferably the chlorides and bromides. Suitable production methods are mentioned, for example, in J. March, Advanced Organic Chemistry, 2nd Edition, p. 377f (1977).
  • the esterification of the polyoxyalkylene ethers takes place by reaction with customary esterification agents, such as carboxylic acids, carboxylic acid halides, carboxylic anhydrides or carboxylic acid esters with C 1 -C 4 -alcohols.
  • esterification agents such as carboxylic acids, carboxylic acid halides, carboxylic anhydrides or carboxylic acid esters with C 1 -C 4 -alcohols.
  • the halides and anhydrides of C 1 -C 40 -alkyl, C 5 -C 10 -cycloalkyl or C 6 -C 18 -arylcarboxylic acids are preferred used.
  • the esterification is generally carried out at temperatures of 0 to 200 ° C, preferably 10 to 100 ° C.
  • the index m indicates the degree of alkoxylation, i. the number of moles of ⁇ -olefin, which are added per mole of formula 20 or 21.
  • Suitable secondary amines for preparing the terpolymers are: didecylamine, ditetradecylamine, distearylamine, dicocosfettamine, ditallow fatty amine and mixtures thereof.
  • the terpolymers have K values (measured according to Ubbelohde in 5% strength by weight solution in toluene at 25 ° C.) of 8 to 100, preferably 8 to 50, corresponding to average molecular weights (M w ) of between about 500 and 100,000. Suitable examples are in EP 606,055 listed.
  • the mixing ratio between A and B can vary within wide limits. Thus, even small amounts of B from 100 ppm to 50,000 ppm, preferably 1,000 ppm to 10,000 ppm, in fatty acid solutions as a cold additive for A. They are able to prevent self-crystallization of the fatty acid, which leads to a lowering of the cloud point, or sedimentation Prevent formed crystals and thus allow easy handling at reduced temperatures. However, for specific problem solutions, from 5% up to 50%, in special cases up to 90% of constituent B, based on the amount of constituent A, may also be present. In particular, the self-sticking point of the additive is lowered and the lubricity of the additized oil is improved. Consequently, the preferred mixing ratio of A: B is between 1:10 and 1: 0.0001, in particular between 1: 4 and 1: 0.0005, especially between 1: 1 and 1: 0.001.
  • the additives according to the invention are added to oils in amounts of from 0.001 to 0.5% by weight, preferably from 0.001 to 0.1% by weight. They may be used as such or dissolved in solvents, such as aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures such as toluene, xylene, ethylbenzene, decane, pentadecane, gasoline fractions, kerosene or commercial solvent mixtures such as Solvent Naphtha, ® Shellsol AB, ® Solvesso 150 , ® Solvesso 200, ® Exxsol, ® Isopar and ® Shellsol D types.
  • solvents such as aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures such as toluene, xylene, ethylbenzene, decane, pentadecane, gasoline fractions, kerosene or commercial solvent mixtures such as Solvent Naphtha, ® Shellsol
  • the additives according to the invention preferably contain 1 to 80%, especially 10 to 70%, in particular 25 to 60%, of solvent.
  • the additives which can be used without problems even at low temperatures of, for example, -40 ° C and lower, improve the lubricity of the additized oils and their cold and corrosion protection properties.
  • the additives according to the invention can also be used together with one or more oil-soluble co-additives, which in themselves improve the cold flow properties and / or lubricity of crude oils, lubricating oils or fuel oils.
  • oil-soluble co-additives are vinyl acetate-containing copolymers or terpolymers of ethylene, comb polymers, alkylphenol-aldehyde resins and oil-soluble amphiphiles.
  • the additives according to the invention are used in admixture with ethylene / vinyl acetate / vinyl neononanoate terpolymers or ethylene / vinyl acetate / vinyl neodecanoate terpolymers to improve the flowability of mineral oils or mineral oil distillates.
  • the terpolymers of vinyl neononanoate or vinyl neodecanoate contain, in addition to ethylene, 10 to 35% by weight of vinyl acetate and 1 to 25% by weight of the respective neo compound.
  • copolymers contain besides ethylene and 10 to 35% by weight of vinyl esters or from 0.5 to 20% by weight of olefins such as diisobutylene, 4-methylpentene or norbornene.
  • the mixing ratio of the additives according to the invention with the ethylene-vinyl acetate copolymers described above or the terpolymers of ethylene, vinyl acetate and the vinyl esters of neononanic or neodecanoic acid is (in parts by weight) 20: 1 to 1:20, preferably 10: 1 to 1: 10th
  • these alkylphenol-formaldehyde resins are those of the formula in which R 51 is C 4 -C 50 -alkyl or -alkenyl, R 50 is ethoxy- and / or propoxy, n is a number from 5 to 100 and p is a number from 0 to 50.
  • the additives according to the invention are used together with comb polymers.
  • This term refers to polymers in which hydrocarbon radicals having at least 8, in particular at least 10, carbon atoms are bonded to a polymer backbone.
  • they are homopolymers whose alkyl side chains contain at least 8 and in particular at least 10 carbon atoms.
  • at least 20%, preferably at least 30% of the monomers have side chains (cf. Comb-like Polymers-Structure and Properties; NA Platé and VP Shibaev, J. Polym. Sci. Macromolecular Revs. 1974, 8, 117 ff ).
  • Suitable comb polymers are, for example, fumarate / vinyl acetate copolymers (cf. EP 0 153 176 A1 ), Copolymers of a C 6 -C 24 ⁇ -olefin and a NC 6 -C 22 -alkylmaleimide (cf. EP 0 320 766 Further, esterified olefin / maleic anhydride copolymers, polymers and copolymers of ⁇ -olefins and esterified copolymers of styrene and maleic anhydride.
  • the mixing ratio (in parts by weight) of the inventive additives with resins or comb polymers is 1:10 to 20: 1, preferably 1: 1 to 10: 1.
  • the additives according to the invention are suitable for improving the lubricating properties of animal, vegetable, mineral or synthetic fuel oils with only low dosing rates. Due to their improved cold properties can be dispensed with storage and application to a warming and / or dilution. In addition, they simultaneously improve the refrigeration and Corrosion protection properties of the additized oils. The emulsifying properties of the additized oils are less affected than is the case with the lubricating additives of the prior art.
  • the additives of the invention are particularly well suited for use in middle distillates. As middle distillates are in particular those mineral oils which are obtained by distillation of crude oil and boil in the range of 120 to 450 ° C, for example kerosene, jet fuel, diesel and fuel oil.
  • the oils may also contain or consist of alcohols such as methanol and / or ethanol.
  • the additives of the invention are used in middle distillates containing 0.05% by weight of sulfur and less, more preferably less than 350 ppm of sulfur, more preferably less than 200 ppm of sulfur and in special cases less than 50 ppm of sulfur. These are generally those middle distillates that have been subjected to a hydrogenating refining, and therefore contain only small amounts of polyaromatic and polar compounds that give them a natural lubricating effect.
  • the additives according to the invention are furthermore preferably used in middle distillates which have 95% distillation points below 370.degree. C., in particular 350.degree. C. and in special cases below 330.degree. They can also be used as components in lubricating oils.
  • the mixtures can be used alone or together with other additives, e.g. with other pour point depressants or dewaxing aids, with corrosion inhibitors, antioxidants, sludge inhibitors, dehazers, conductivity improvers, lubricity additives, and cloud point depressant additives. Furthermore, they are successfully used in conjunction with additive packages, which i.a. known ashless dispersing additives, detergents, defoamers and corrosion inhibitors.
  • Table 1 Own point (pour point) of the additives of the invention Composition (parts by weight) Pour point example A1 A2 B1 B4 1 80 20 -9 2 50 50 -24 3 20 80 0 4 80 20 -9 5 50 50 -18 6 20 80 -15 7 80 20 -27 8th 50 50 -27 9 20 80 -6 10 80 20 -21 11 50 50 -21 12 20 80 -9 13 * 99.95 0.05 -36 14 * 99.95 0.05 -36 15 99.95 0.05 -15 V1 100 -9 V2 100 6 V3 100 9 V4 100 -6 V5 * 100 -36 * These examples are obtained with a 50% by weight adjustment of the fatty acid in solvent naphtha.
  • Composition (parts by weight) Cloud point example A1 A2 B1 B4 V6 * 100 -27.0 16. * 99.9995 0.0005 -33.0 17 * 99.9995 0.0005 -30.5 18 * 99,998 0,002 -33.5 19 * 99,998 0,002 -33.5 20 * 99.995 0.005 -31.0 21 * 99.995 0.005 -32.2 * These examples were obtained with a 50% by weight adjustment of the fatty acid in solvent naphtha.
  • MS is a mixture of a number of aliphatic and cyclic non-aromatic hydrocarbons.
  • the main components of MS can be found in the following table: Table 6: Components of MS component Concentration range (wt%) Di-2-ethylhexyl 10 - 25 2-ethylhexyl acid-2-ethylhexyl 10 - 25 C 16 lactones 4 - 20 2-Ethylhexylbutyrat 3 - 10 2-ethylhexanediol- (1,3) glycol mono-n-butyrate 5 - 15 2-ethylhexanol 4 - 10 C 4 to C 8 acetates 2 - 10 2-ethylhexanediol- (1,3) 2 - 5 Ethers and esters ⁇ C 20 0 - 20
  • the lubricating effect of the additives was carried out using an HFRR instrument from PCS Instruments on additized oils at 60 ° C.
  • the High Frequency Reciprocating Rig Test (HFRR) is described in D. Wei, H. Spikes, Wear, Vol. 111, No.2, p.217, 1986 , The results are given as coefficient of friction and Wear Scar (WS1.4). A low coefficient of friction and a low Wear Scar show a good lubricating effect.
  • test oils having the following characteristics were used: Test oil 1 Test oil 2 boiling range: 170 - 344 ° C 182-304 ° C density 0.830 g / cm 3 0.821 g / cm 3 Cloud point -9 ° C -33 ° C sulfur content 45 ppm 6 ppm

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Claims (16)

  1. Additifs stables au froid pour huiles combustibles d'une teneur en soufre allant jusqu'à 0,05 % en poids, contenant des mélanges d'acides gras composés de :
    A1) 1 à 99 % en poids d'au moins un acide mono- ou dicarboxylique saturé ayant de 6 à 50 atomes de carbone,
    A2) 1 à 99 % en poids d'au moins un acide mono- ou dicarboxylique insaturé ayant de 6 à 50 atomes de carbone,
    et
    B) au moins un composé azoté polaire, actif en tant que dispersant de paraffine dans les distillats moyens, présent dans une quantité allant de 0,01 à 90 % en poids par rapport au poids total des composants A1), A2) et B), qui comprend des terpolymères à base d'anhydrides d'acide dicarboxylique α,β-insaturés, de composés α,β-insaturés et d'éthers de polyoxyalkylène et d'alcools inférieurs insaturés, qui sont caractérisés en ce qu'ils contiennent
    de 20 à 80 % en mole de motifs structuraux bivalents des formules 12 et/ou 14, et éventuellement 13, les motifs structuraux 13 étant issus de radicaux anhydride n'ayant pas réagi,
    Figure imgb0049
    Figure imgb0050
    Figure imgb0051
     où
    R22 et R23 représentent, indépendamment l'un de l'autre, l'hydrogène ou un groupe méthyle,
    a, b valent zéro ou un et a + b vaut un,
    R24 et R25 sont identiques ou différents et représentent les groupes -NHR6, N (R6)2 et/ou -OR27, et R27 représente un cation de formule H2N(R6)2 ou H3NR6,
    Figure imgb0052
    de 19 à 80 % en mole de motifs structuraux bivalents de formule 15
    Figure imgb0053
     où
    R28 représente l'hydrogène ou un groupe alkyle en C1 à C4 et
    R29 un groupe alkyle en C6 à C60 ou aryle en C6 à C18, et
    de 1 à 30 % en mole de motifs structuraux bivalents de formule 16
    Figure imgb0054
     où
    R30 représente l'hydrogène ou un groupe méthyle,
    R31 l'hydrogène ou un groupe alkyle en C1 à C4,
    R33 un groupe alkylène en C1 à C4,
    m vaut de 1 à 100,
    R32 représente un groupe alkyle en C1 à C24, cycloalkyle en C5 à C20, aryle en C6 à C18 ou -C (O) -R34, et où
    R34 représente un groupe alkyle en C1 à C40, cycloalkyle en C5 à C10 ou aryle en C6 à C18.
  2. Additifs selon la revendication 1, dans lesquels le composant A comprend des acides carboxyliques ayant de 12 à 22 atomes de carbone.
  3. Additifs selon la revendication 1 et/ou 2, contenant de 1 à moins de 20 % en poids de composant A1) et plus de 80 à 99 % en poids de composant A2).
  4. Additifs selon une ou plusieurs des revendications 1 à 3, dans lesquels le mélange des composés A1) et A2) présente un indice d'iode d'au moins 40 g I/100 g.
  5. Additifs selon une ou plusieurs des revendications 1 à 4, dans lesquels le mélange des composés A1) et A2) comprend de 1 à 40 % en poids d'acides résiniques.
  6. Additifs selon une ou plusieurs des revendications 1 à 5, dans lesquels le composant B) contient de 40 à 60 % en mole de motifs structuraux bivalents des formules 12 et/ou 14, et éventuellement 13, de 39 à 60 % en mole de motifs structuraux bivalents de formule 15 et de 1 à 20 % en mole de motifs structuraux bivalents de formule 16.
  7. Additifs selon une ou plusieurs des revendications 1 à 6, dans lesquels les motifs structuraux des formules 12 à 14 sont dérivés de l'anhydride maléique, de l'anhydride itaconique ou de l'anhydride citraconique.
  8. Additifs selon une ou plusieurs des revendications 1 à 7, dans lesquels les motifs structuraux de formule 15 sont dérivés du styrène, de 1'α-méthylstyrène, du diméthylstyrène, de l'α-éthylstyrène, du diéthylstyrène, de l'i-propylstyrène, du tert.-butylstyrène, diisobutylène, décène, dodécène, tétradécène, pentadécène, hexadécène, octadécène, d'une α-oléfine en C20, d'une α-oléfine en C24, d'une α-oléfine en C30, du tripropényle, tétrapropényle, pentapropényle et de leurs mélanges.
  9. Additifs selon une ou plusieurs des revendications 1 à 8, dans lesquels les monomères de formule 20 sont produits par addition d'oxyde d'éthylène, d'oxyde de propylène et/ou d'oxyde de butylène sur l'alcool allylique, l'alcool méthallylique, le 3-butèn-1-ol, le 1-butèn-3-ol, le 2-méthyl-3-butèn-1-ol, le 2-méthyl-3-butèn-2-ol et le 3-méthyl-3-butèn-1-ol.
  10. Additifs selon une ou plusieurs des revendications 1 à 9, dans lesquels les amines utilisées dans la production des terpolymères sont choisies parmi la n-hexylamine, la n-octylamine, la n-tétradécylamine, la n-hexadécylamine, la n-stéarylamine, la N,N-diméthylaminopropylène diamine, la cyclohexylamine, la déhydroabiétylamine, la didécylamine, la ditétradécylamine, la distéarylamine, la diamine de coprah, la diamine de suif et leurs mélanges.
  11. Additifs selon une ou plusieurs des revendications 1 à 10, dans lesquels les terpolymères possèdent des valeurs K allant de 8 à 100 (mesurées selon Ubbelohde dans une solution à 5 % en poids de toluène à 25 °C).
  12. Solutions stables au froid d'additifs selon une ou plusieurs des revendications 1 à 11 dans des solvants organiques, les solutions contenant de 1 à 80 % en poids de solvant.
  13. Solutions stables au froid selon la revendication 12, dans lesquelles le solvant consiste en des hydrocarbures aliphatiques et/ou aromatiques et/ou oxygénés.
  14. Mélanges d'acides gras stables au froid composés de :
    A1) 1 à 99 % en poids d'au moins un acide mono- ou dicarboxylique saturé ayant de 6 à 50 atomes de carbone,
    A2) 1 à 99 % en poids d'au moins un acide mono- ou dicarboxylique insaturé ayant de 6 à 50 atomes de carbone,
    et
    B) au moins un composé azoté polaire, actif en tant que dispersant de paraffine dans les distillats moyens, présent dans une quantité allant de 0,01 à 90 % en poids par rapport au poids total des composants A1), A2) et B), qui comprend des terpolymères à base d'anhydrides d'acide dicarboxylique α,β-insaturés, de composés α,β-insaturés et d'éthers de polyoxyalkylène et d'alcools inférieurs insaturés, qui sont caractérisés en ce qu'ils contiennent
    de 20 à 80 % en mole de motifs structuraux bivalents des formules 12 et/ou 14, et éventuellement 13, les motifs structuraux 13 étant issus de radicaux anhydride n'ayant pas réagi,
    Figure imgb0055
    Figure imgb0056
    Figure imgb0057
     où
    R22 et R23 représentent, indépendamment l'un de l'autre, l'hydrogène ou un groupe méthyle,
    a, b valent zéro ou un et a + b vaut un,
    R24 et R25 sont identiques ou différents et représentent les groupes -NHR6, N(R6)2 et/ou -OR27 , et R27 représente un cation de formule H2N(R6)2 ou H3NR6,
    de 19 à 80 % en mole de motifs structuraux bivalents de formule 15
    Figure imgb0058
     où
    R28 représente l'hydrogène ou un groupe alkyle en C1 à C4 et
    R29 un groupe alkyle en C6 à C60 ou aryle en C6 à C18, et
    de 1 à 30 % en mole de motifs structuraux bivalents de formule 16
    Figure imgb0059
     où
    R30 représente l'hydrogène ou un groupe méthyle,
    R31 l'hydrogène ou un groupe alkyle en C1 à C4,
    R33 un groupe alkylène en C1 à C4,
    m vaut de 1 à 100,
    R32 représente un groupe alkyle en C1 à C24, cycloalkyle en C5 à C20, aryle en C6 à C18 ou -C (O) -R34, et où .
    R34 représente un groupe alkyle en C1 à C40, cycloalkyle en C5 à C10 ou aryle en C6 à C18.
  15. Huiles combustibles, contenant, outre un distillat moyen dont la teneur en soufre va jusqu'à 0,05 % en poids, un additif selon une ou plusieurs des revendications 1 à 14.
  16. Utilisation d'additifs selon une ou plusieurs des revendications 1 à 14 pour améliorer le pouvoir lubrifiant de distillats moyens pauvres en soufre, dont la teneur en soufre va jusqu'à 0,05 % en poids.
EP01126254A 2000-11-24 2001-11-06 Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant Expired - Lifetime EP1209215B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP07005871A EP1801188B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant
EP07005870A EP1803791B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10058359A DE10058359B4 (de) 2000-11-24 2000-11-24 Brennstofföle mit verbesserter Schmierwirkung, enthaltend Mischungen aus Fettsäuren mit Paraffindispergatoren, sowie ein schmierverbesserndes Additiv
DE10058359 2000-11-24

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP07005870A Division EP1803791B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant
EP07005871A Division EP1801188B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant

Publications (3)

Publication Number Publication Date
EP1209215A2 EP1209215A2 (fr) 2002-05-29
EP1209215A3 EP1209215A3 (fr) 2003-08-13
EP1209215B1 true EP1209215B1 (fr) 2007-10-10

Family

ID=7664508

Family Applications (3)

Application Number Title Priority Date Filing Date
EP01126254A Expired - Lifetime EP1209215B1 (fr) 2000-11-24 2001-11-06 Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant
EP07005870A Revoked EP1803791B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant
EP07005871A Expired - Lifetime EP1801188B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant

Family Applications After (2)

Application Number Title Priority Date Filing Date
EP07005870A Revoked EP1803791B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant
EP07005871A Expired - Lifetime EP1801188B1 (fr) 2000-11-24 2001-11-06 Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant

Country Status (6)

Country Link
US (3) US6610111B2 (fr)
EP (3) EP1209215B1 (fr)
JP (1) JP5317380B2 (fr)
CA (1) CA2363700C (fr)
DE (4) DE10058359B4 (fr)
ES (1) ES2295098T3 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI122428B2 (fi) * 2002-08-05 2021-01-29 Arizona Chemical Rasvahappokoostumus ja sen käyttö
US7597725B2 (en) * 2002-10-04 2009-10-06 Infineum International Ltd. Additives and fuel oil compositions
DE10313883A1 (de) * 2003-03-27 2004-10-07 Basf Ag Additivgemisch zur Verbesserung der Schmierfähigkeitseigenschaften von Mineralölprodukten
US8287608B2 (en) * 2005-06-27 2012-10-16 Afton Chemical Corporation Lubricity additive for fuels
EP1770151A1 (fr) * 2005-09-30 2007-04-04 Infineum International Limited Concentré d'additifs
EP1979445A1 (fr) * 2006-01-18 2008-10-15 Basf Se Utilisation de mélanges d'acides monocarboxyliques et de composés d'hydrocarbures polycycliques pour améliorer la stabilité au stockage de concentrés d'additifs de carburants
WO2008057624A2 (fr) * 2006-04-05 2008-05-15 Baker Hughes Incorporated Additifs de carburant utiles pour réduire les émissions de particules
US20080141579A1 (en) * 2006-12-13 2008-06-19 Rinaldo Caprotti Fuel Oil Compositions
WO2009131024A1 (fr) * 2008-04-25 2009-10-29 株式会社Adeka Agent d’amélioration de la fluidité à basse température pour carburant biodiesel
WO2010115766A1 (fr) * 2009-04-07 2010-10-14 Basf Se Mélange de composés azotés polaires solubles dans l'huile et de composés aliphatiques solubles dans l'huile servant à abaisser le point de trouble de combustibles de distillat moyen
EP2535396B1 (fr) * 2010-02-10 2017-04-19 NOF Corporation Méthode avec des agents d'amélioration de la fluidité pour les matières grasses et les huiles végétales
ES2548213T3 (es) * 2011-03-29 2015-10-14 Nof Corporation Agente para mejorar el flujo del fuelóleo y composición de fuelóleo
RU2561279C1 (ru) * 2014-09-19 2015-08-27 Общество с ограниченной ответственностью "Научно-производственное предприятие КВАЛИТЕТ" (ООО "НПП КВАЛИТЕТ") Диспергатор парафинов, способ его получения и топливная композиция, его содержащая
CN104403706B (zh) * 2014-11-20 2016-06-22 中国石油大学(北京) 一种新型柴油蜡晶分散剂
WO2017144378A1 (fr) * 2016-02-23 2017-08-31 Basf Se Acides polycarboxyliques hydrophobes utilisés comme additifs réducteurs d'usure par frottement dans des carburants
EP3272837B1 (fr) * 2016-07-21 2021-01-27 Bharat Petroleum Corporation Limited Composition de combustible contenant un agent d'amélioration de pouvoir lubrifiant et procédé associé

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2793A (en) * 1842-09-30 Joel g
US2487189A (en) * 1946-05-28 1949-11-08 Gulf Oil Corp Diesel fuel oils
WO1985001496A1 (fr) 1983-10-03 1985-04-11 American Telephone & Telegraph Company Housse de protection pour robot
CA1282240C (fr) 1984-02-21 1991-04-02 Albert Rossi Mazout a teneur de polymere d'alkylester
US4569679A (en) * 1984-03-12 1986-02-11 Exxon Research & Engineering Co. Additive concentrates for distillate fuels
GB8630594D0 (en) * 1986-12-22 1987-02-04 Exxon Chemical Patents Inc Chemical compositions
US5039437A (en) * 1987-10-08 1991-08-13 Exxon Chemical Patents, Inc. Alkyl phenol-formaldehyde condensates as lubricating oil additives
DE3742630A1 (de) 1987-12-16 1989-06-29 Hoechst Ag Polymermischungen fuer die verbesserung der fliessfaehigkeit von mineraloeldestillaten in der kaelte
DE3926992A1 (de) 1989-08-16 1991-02-21 Hoechst Ag Verwendung von umsetzungsprodukten von alkenylspirobislactonen und aminen als paraffindispergatoren
DE4237662A1 (de) 1992-11-07 1994-05-11 Basf Ag Erdölmitteldestillatzusammensetzungen
ES2110124T3 (es) 1993-01-06 1998-02-01 Clariant Gmbh Termopolimeros a base de anhidridos de acidos carboxilicos alfa,beta-insaturados, de compuestos alfa,beta-insaturados y de polioxialquileneteres de alcoholes inferiores insaturados.
GB9411614D0 (en) * 1994-06-09 1994-08-03 Exxon Chemical Patents Inc Fuel oil compositions
JPH08134476A (ja) * 1994-11-14 1996-05-28 Cosmo Sogo Kenkyusho:Kk 低硫黄分軽油組成物
DE69518404T2 (de) * 1994-12-13 2001-01-25 Infineum Usa Lp Ölbrennstoffzusammensetzungen umfassend ölbrennstoffe auf petroleumbasis, ethylen-ungesättigte ester-copolymere und ester von mehrwertigen alkoholen mit carbonsäuren
GB9502041D0 (en) 1995-02-02 1995-03-22 Exxon Chemical Patents Inc Additives and fuel oil compositions
JP3829948B2 (ja) * 1995-03-24 2006-10-04 出光興産株式会社 ディーゼル軽油組成物
ATE202595T1 (de) * 1995-12-22 2001-07-15 Exxonmobil Res & Eng Co Benzinzusatzkonzentrat
US5755834A (en) * 1996-03-06 1998-05-26 Exxon Chemical Patents Inc. Low temperature enhanced distillate fuels
JPH09255973A (ja) 1996-03-25 1997-09-30 Oronaito Japan Kk 軽油添加剤及び軽油組成物
GB9610363D0 (en) * 1996-05-17 1996-07-24 Ethyl Petroleum Additives Ltd Fuel additives and compositions
DE19620119C1 (de) * 1996-05-18 1997-10-23 Hoechst Ag Terpolymerisate des Ethylens, ihre Herstellung und ihre Verwendung als Additive für Mineralöldestillate
DE19622052A1 (de) 1996-05-31 1997-12-04 Basf Ag Paraffindispergatoren für Erdölmitteldestillate
FR2751982B1 (fr) * 1996-07-31 2000-03-03 Elf Antar France Additif d'onctuosite pour carburant moteurs et composition de carburants
EP0829527A1 (fr) * 1996-09-12 1998-03-18 Exxon Research And Engineering Company Concentré additif pour des compositions de combustibles
JP3841368B2 (ja) * 1996-10-07 2006-11-01 花王株式会社 低硫黄軽油用油性向上剤及び低硫黄軽油組成物
JP3968820B2 (ja) * 1997-06-13 2007-08-29 日本油脂株式会社 燃料油組成物
WO1999036489A1 (fr) * 1998-01-13 1999-07-22 Baker Hughes Incorporated Composition et procede permettant d'ameliorer le pouvoir lubrifiant des combustibles
JP3725347B2 (ja) * 1998-09-09 2005-12-07 三洋化成工業株式会社 燃料油低温流動性向上剤および燃料油組成物
US6051039A (en) * 1998-09-14 2000-04-18 The Lubrizol Corporation Diesel fuel compositions
CA2387329A1 (fr) * 1999-11-23 2001-05-31 David Daniels Composition
EP1116780B1 (fr) * 2000-01-11 2005-08-31 Clariant GmbH Additif polyfonctionnel pour huiles combustibles

Also Published As

Publication number Publication date
EP1803791B1 (fr) 2009-02-18
EP1209215A2 (fr) 2002-05-29
CA2363700C (fr) 2010-04-06
DE50113115D1 (de) 2007-11-22
EP1209215A3 (fr) 2003-08-13
DE50114719D1 (de) 2009-04-02
ES2295098T3 (es) 2008-04-16
DE50114718D1 (de) 2009-04-02
EP1801188B1 (fr) 2009-02-18
US20020095857A1 (en) 2002-07-25
EP1803791A3 (fr) 2007-10-03
EP1801188A3 (fr) 2007-10-03
EP1803791A2 (fr) 2007-07-04
US20040083644A1 (en) 2004-05-06
DE10058359A1 (de) 2002-06-06
DE10058359B4 (de) 2005-12-22
JP2002167586A (ja) 2002-06-11
CA2363700A1 (fr) 2002-05-24
EP1801188A2 (fr) 2007-06-27
USRE40758E1 (en) 2009-06-23
US6610111B2 (en) 2003-08-26
JP5317380B2 (ja) 2013-10-16

Similar Documents

Publication Publication Date Title
EP2038380B1 (fr) Mélange constitué de composés d'azote polaires oléosolubles et d'amides d'acides en tant que dispersant de paraffine pour des carburants
EP1209217B1 (fr) Huiles combustibles à pouvoir lubrifiant amélioré, contenant des produits de réaction d'acides gras avec des amines solubles dans l'huile à chaînes courtes
EP1209215B1 (fr) Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant
EP1692196B1 (fr) Compositions d'huiles combustibles presentant de meilleures proprietes d'ecoulement a froid
DE10357878C5 (de) Brennstofföle aus Mitteldestillaten und Ölen pflanzlichen oder tierischen Ursprungs mit verbesserten Kälteeigenschaften
EP1116781B1 (fr) Additif polyfonctionnel pour huiles combustibles
EP1116780B1 (fr) Additif polyfonctionnel pour huiles combustibles
EP0900836B2 (fr) Additif pour améliorer l'écoulement d'huiles minérales et de distillats d'huile minérale
EP1124916B1 (fr) Emulsionnants de paraffine a effet lubrifiant pour distillats de produits petroliers
EP1209216B1 (fr) Mélanges d'acides gras à stabilité à froid améliorée, lesquelles contiennent des polymères en peigne, ainsi que utilisation de ceux-là dans des huiles combustibles
EP2129752A1 (fr) Mélange d'agents qui améliorent l'écoulement à froid et d'amines
EP1469019B1 (fr) Compositions et leur utilisation pour l'amélioration des propriétés d'écoulement à froid des distillats moyens, ainsi que huile combustible contenant lesdites compositions
EP0997517B1 (fr) Mélanges polymères pour l'amélioration de l'action lubrifiante de distillats moyens
EP1380634B1 (fr) Additifs lubrifiant stabilisés contre l'oxydation pour huiles combustibles hautement désulfurées.
EP2417229B1 (fr) Mélange de composés azotés polaires solubles dans l'huile et de composés aliphatiques solubles dans l'huile servant à abaisser le cloud point dans les carburants diesel
EP1380633B1 (fr) Utilisation de liquides huileux contre l'oxydation des huiles combustibles
EP4127106B1 (fr) Compositions et procédés de dispersion des paraffines dans des huiles de combustible à faible teneur en soufre
DE10136828B4 (de) Schmierverbessernde Additive mit verminderter Emulgierneigung für hochentschwefelte Brennstofföle
DE10252973A1 (de) Oxidationsstabilisierte Schmieradditive für hochentschwefelte Brennstofföle
DE10000650C2 (de) Mehrfunktionelles Additiv für Brennstofföle
DE19856270A1 (de) Polymermischung zur Verbesserung der Schmierwirkung von Mitteldestillaten
DE10048682A1 (de) Mehrfunktionelles Additiv für Brennstofföle

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

17P Request for examination filed

Effective date: 20040213

AKX Designation fees paid

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH

17Q First examination report despatched

Effective date: 20050824

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RIC1 Information provided on ipc code assigned before grant

Ipc: C10L 10/08 20060101ALI20070226BHEP

Ipc: C10L 1/188 20060101ALI20070226BHEP

Ipc: C10L 1/234 20060101ALI20070226BHEP

Ipc: C10L 10/04 20060101AFI20070226BHEP

Ipc: C10L 10/14 20060101ALI20070226BHEP

RBV Designated contracting states (corrected)

Designated state(s): BE DE ES FI FR GB NL SE

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE ES FI FR GB NL SE

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REF Corresponds to:

Ref document number: 50113115

Country of ref document: DE

Date of ref document: 20071122

Kind code of ref document: P

REG Reference to a national code

Ref country code: SE

Ref legal event code: TRGR

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 20080213

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2295098

Country of ref document: ES

Kind code of ref document: T3

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20080711

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20081021

Year of fee payment: 8

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20110401

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20110322

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20091107

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20151104

Year of fee payment: 15

Ref country code: GB

Payment date: 20151020

Year of fee payment: 15

Ref country code: FI

Payment date: 20151119

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20151014

Year of fee payment: 15

Ref country code: BE

Payment date: 20151029

Year of fee payment: 15

Ref country code: NL

Payment date: 20151015

Year of fee payment: 15

Ref country code: FR

Payment date: 20151030

Year of fee payment: 15

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20161130

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 50113115

Country of ref document: DE

REG Reference to a national code

Ref country code: SE

Ref legal event code: EUG

REG Reference to a national code

Ref country code: NL

Ref legal event code: MM

Effective date: 20161201

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20161106

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20161106

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20170731

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20161107

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20161201

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20161130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20170601

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20161106

REG Reference to a national code

Ref country code: BE

Ref legal event code: MM

Effective date: 20161130