EP1685216B1 - Rezeptur aus Mineralöl und einer Additivmischung - Google Patents
Rezeptur aus Mineralöl und einer Additivmischung Download PDFInfo
- Publication number
- EP1685216B1 EP1685216B1 EP04790006A EP04790006A EP1685216B1 EP 1685216 B1 EP1685216 B1 EP 1685216B1 EP 04790006 A EP04790006 A EP 04790006A EP 04790006 A EP04790006 A EP 04790006A EP 1685216 B1 EP1685216 B1 EP 1685216B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mass
- mineral oil
- ethylene
- vinyl acetate
- additive
- 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.)
- Not-in-force
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
- 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
- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/1955—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds 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 an alcohol, ether, aldehyde, ketonic, ketal, acetal radical
-
- 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
-
- 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
- C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
- C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
-
- 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
- C10L2300/00—Mixture of two or more additives covered by the same group of C10L1/00 - C10L1/308
- C10L2300/30—Mixture of three components
Definitions
- the invention relates to a formulation of mineral oil as the main component and small proportions of an additive mixture, and to a method for producing a formulation of mineral oil as the main component and small proportions of an additive mixture.
- Formulations of mineral oils as the main component and small amounts of additive mixtures of conventional unmodified ethylene-vinyl acetate copolymers, hydrocarbon polymers, esterified maleic anhydride-olefin copolymers, polar nitrogen compounds such as amine salts of polybasic carboxylic acids and esterified polyoxyalkylenes are known ( WO 94/10267 A1 . WO 95/33 012 A1 . EP 0 921 183 A1 . WO 93/14178 A1 . EP 0 889 323 A1 ).
- Disadvantages are the insufficient flow behavior and the shelf life of these formulations at low temperatures and the limited lubricity of the formulations when the mineral oil component has a sulfur content below 0.005% by mass.
- the object of the invention is an additive mixture as part of a formulation of mineral oil as the main component and small proportions of an additive mixture, which has an improved flow behavior and improved storage stability at low temperatures and improved Has lubricity.
- the improved flow behavior is intended to achieve energy savings in the pump units, by means of which these recipes are transported.
- the development of the additive mixtures is to be carried out from the viewpoint of the use of mineral oils with very low sulfur content in order to achieve fuels of improved environmental compatibility with regard to the pollutant emissions of vehicles.
- vinyl ester components which may be contained in the modified ethylene-vinyl ester copolymers are vinyl acetate, vinyl propionate, 2-ethylhexyl vinyl ester, vinyl laurate, 2-hydroxyethyl vinyl ester and 4-hydroxybutyl vinyl ester.
- the ethylene-vinyl ester copolymers may contain as further unsaturated ester components 1 to 30% by weight, based on the vinyl ester, of (meth) acrylic acid esters such as methyl acrylate, methyl methacrylate, ethyl methacrylate, butyl acrylate, 2-ethylhexyl acrylate, ethylene glycol dimethacrylate, dodecyl acrylate or hydroxyethyl methacrylate and / or vinyl ethers such as octyl vinyl ether or hexanediol monovinyl ether.
- acrylic acid esters such as methyl acrylate, methyl methacrylate, ethyl methacrylate, butyl acrylate, 2-ethylhexyl acrylate, ethylene glycol dimethacrylate, dodecyl acrylate or hydroxyethyl methacrylate and / or vinyl ethers such as octyl vinyl
- Modification of the ethylene-vinyl ester copolymers by polar groups consists of reacting the ethylene-vinyl ester-vinyl alcohol copolymers with aldehydes to give hemiacetals or grafting polar, ethylenically unsaturated monomers onto the copolymer.
- the polar group-modified ethylene-vinyl ester copolymers contained in the additive mixture are, on the one hand, hemiacetals of ethylene-vinyl ester-vinyl alcohol copolymers with butyraldehyde.
- hemiacetals of ethylene-vinyl ester-vinyl alcohol copolymers with butyraldehyde are hemiacetals of ethylene-vinyl acetate-vinyl alcohol copolymers, according to DD 295 507 A7 have been reacted in heterogeneous phase with butyraldehyde.
- the graft modification of the ethylene-vinyl acetate copolymers can be carried out by reaction with the unsaturated monomers in the extruder ( DD 282 462 B5 ) or in the stirred reactor ( DD 293 125 B5 ) in the presence of thermally decomposing radical formers. It is also possible to carry out the modification in the preparation of the copolymer by the high-pressure process by metering the monomers into the polymer melt in the low-pressure separator or in the discharge extruder.
- the vinyl acetate grafted ethylene-vinyl acetate copolymers have molecular weight average molecular weights of from 800 to 5,000 and a total vinyl acetate content of from 20 to 60% by weight, with the vinyl acetate content of the copolymer backbone being 10 to 40% by weight and the grafted vinyl acetate side chains being 10 to 20% by weight.
- the modified ethylene-vinyl ester copolymers may contain up to 35% by weight of poly-C 6 -C 36 alkyl (meth) acrylates and / or unmodified ethylene-vinyl ester copolymers.
- polyalcohols which are contained as alcohol component in the esters of C 2 -C 6 polyalcohols and C 12 -C 40 monocarboxylic acids b) of the additive mixture are ethylene glycol, polyalkylene glycols, glycerol, 1,1,1-tris (hydroxymethyl ) propane, pentaerythritol and sorbitol.
- Examples of C 12 -C 40 -monocarboxylic acids which are contained as carboxylic acid component in the esters of C 2 -C 6 -polyalcohols with C 12 -C 40 -monocarboxylic acids b) of the additive mixture are lauric acid, palmitic acid, stearic acid, oleic acid, elaidic acid, Ricinoleic acid, eleostearic acid, linoleic acid, linolenic acid and erucic acid, or dimer acids based on oleic acid or linolenic acid.
- esters of C 2 -C 6 -polyalcohols with C 12 -C 40 -monocarboxylic acids b) are mixed esters of polyalcohols in which the polyalcohols are esterified by mixtures of C 12 -C 40 -monocarboxylic acids.
- Specific examples of the esters of C 2 -C 6 polyalcohols with C 12 -C 40 monocarboxylic acids are the monoesters of ethylene glycol with dilinolenic acid, a C 36 dimer acid, the diesters of propylene glycol with oleic acid and the triesters of pentaerythritol with stearic acid ,
- esters of C 2 -C 6 polyalcohols and C 12 -C 40 monocarboxylic acids b) are esters of unsaturated C 16 -C 24 monocarboxylic acids with C 3 -C 4 polyalcohols, the proportion of C 22 monocarboxylic acids , based on the total mass of C 16 -C 24 monocarboxylic acids, 45 to 52% by mass.
- Examples of unsaturated C 16 -C 24 -monocarboxylic acids which may be contained in the preferred esters of unsaturated C 16 -C 24 -monocarboxylic acids with C 3 -C 4 -polyalcohols as additive component b) are oleic acid, linoleic acid, linolenic acid and erucic acid.
- Suitable vinylaromatics as comonomers which may be present as monomer components in the partially and / or completely imidized copolymers of ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides c) of the additive mixtures are styrene, ⁇ -methylstyrene and vinylpyridine.
- Examples of suitable C 2 -C 36 - ⁇ -olefins as comonomers which may be present as monomer components in the partially and / or completely imidized copolymers of ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides c) of the additive mixtures are ethylenically unsaturated monomers of Type C 2 -C 20 olefins, C 4 -C 21 acrylic esters, C 5 -C 22 methacrylic acid esters, C 5 -C 14 vinyl silanes, C 6 -C 15 acrylatesilanes, acrylic acid, methacrylic acid, acrylonitrile, vinyloxazoline , Isopropenyloxazoline, vinyl pyrrolidone, amino C 1 -C 8 alkyl (meth) acrylates, C 3 -C 20 vinyl esters, C 3 -C 20 vinyl ethers and / or hydroxy C 1 -C 8 alkyl (meth
- Preferred comonomers as monomer components in the partially and / or completely imidized copolymers of ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides c) of the additive mixtures are isobutylene, diisobutylene, vinyl acetate, styrene and ⁇ -methylstyrene.
- the partially imidized copolymers of C 4 -C 20 -ethylenically unsaturated acid anhydrides and vinylaromatics and / or C 2 -C 36 - ⁇ -olefins as additive component c) preferably have a molar ratio of 1 : 1 to 1: 9 and weight average molecular weight of 5,000 to 500,000, in which the partial imidization with ammonia, C 1 -C 24 -monoalkylamines, C 6 -C 18 -aromatic monoamines, C 2 -C 18 -monoamino alcohols, monoaminated poly (C 2 -C 4 -alkylene) oxides of a Molar mass of 400 to 3000, and / or mono-etherified poly (C 2 -C 4 -alkylene) oxides having a molecular weight of 100 to 10,000 is carried out, wherein the molar ratio of anhydride copolymer / ammonia, amino groups C 1 -C 24 mono
- Particularly suitable as partially imidized copolymers of ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides c) are C 12 -C 24 monoalkylamines such as oleylamine, dodecylamine, hexadecylamine, octadecylamine or eicosylamine, monosubstituted diamines of the N-dodecyl-1 type, 3-diaminopropane, N-octadecyl-1,3-diaminopropane or N-octadecylpropylene triamine or amino alcohols such as aminodecan-10-ol or aminohexadecan-16-ol imidated maleic anhydride copolymers.
- monoalkylamines such as oleylamine, dodecylamine, hexadecylamine, octadecylamine or eicosylamine
- the partially imidized copolymers of unsaturated dicarboxylic anhydrides and vinylaromatics and / or C 2 -C 36 - ⁇ -olefins as additive component c) are particularly preferably maleic anhydride- ⁇ -methylstyrene copolymers which are partially imidized with C 6 -C 24 -monoalkylamines and in which the molar ratio Anhydride groups in the copolymer / bound C 6 -C 24 monoalkylamine in the copolymer 8: 1 to 1.3: 1.
- mineral oils which form the major component in mineral oil formulations and minor proportions of an additive mixture are crude oils and petroleum distillates having a boiling range of 100 to 500 ° C, such as lubricating oils, kerosene, diesel, fuel oil, heavy fuel oils, kerosene, tractor fuel and cracked gasoline.
- the mineral oils may also contain up to 30% by weight of synthesis hydrocarbons from the Fischer-Tropsch synthesis, up to 20% by weight modified vegetable oils based on sunflower oil, soybean oil, Rapeseed oil, or oils of animal origin, biodiesel and / or up to 10% by weight of alcohols such as methanol or ethanol.
- the mineral oils in the formulations of mineral oil and small amounts of an additive mixture are crude oils or fuel oils from a middle distillate with a sulfur content below 0.05% by weight, in particular heating oils, gas oils or diesel oils.
- the preferred content of the additive mixture in mineral oil is 0.01 to 0.3 mass%.
- the mineral oil may further comprise a total of 0 to 200% by weight, based on the sum of the additive components a) and b) or a) and c) or a), b) and c), further additive components of the fatty acid mixture type, polar nitrogen compounds, preferably polyamines, Etheramines, amino alcohols, amine salts, amides or imides of polybasic carboxylic acids; C 7 -C 30 -alcohols, polyalkylene glycols, esters or ethers of polyoxyalkylene compounds, unmodified ethylene-vinyl ester copolymers, hydrocarbon polymers, alkylphenol-aldehyde copolymers, aromatic compounds with C 8 -C 100 -alkyl substituents, carboxylated polyamines, detergents, corrosion inhibitors , Demulsifiers, metal deactivators, cetane improvers, defoamers and / or cosolvents.
- polar nitrogen compounds preferably polyamines, Et
- fatty acid mixtures contained in the mineral oil as further additive components are mixtures of saturated and / or unsaturated C 6 -C 40 -carboxylic acids, such as Lauric acid, palmitic acid, oleic acid, linolenic acid, dimer fatty acids and alkenyl succinic acids.
- polyamine polar nitrogen compounds contained in the mineral oil as further additive components are N-hexadecyl-1,3-diaminopropane, N-octadecyldipropylenetriamine, N-dodecyl-1,3-diaminopropane, N, N'-didodecyl-1,3- diaminopropane and N, N'-dioctadecyl dipropylene triamine.
- Examples of the polar nitrogen compounds of the etheramine type contained in the mineral oil as further additive components are 3-methoxypropylamine, 3-N-octyloxypropyl-1,3-diaminopropane and 3-N- (2,4,6-trimethyldecyloxypropyl) -1,3 -diaminopropan.
- Examples of the polar nitrogen compounds of the amino alcohols type contained in the mineral oil as further additive components are aminopentan-5-ol, aminoundecan-11-ol and 2-amino-2-methylpropanol.
- Examples of the amines used for the amines salts, amides or imides of polybasic carboxylic acids as further additive components are C 8 -C 40 -amines, such as hydrogenated tallamine, tetradecylamine, eicosylamine, dioctadecylamine, methylbehenylamine, N-oleyl-1,3-amines. diaminopropane, N-stearyl-1-methyl-1,3-diaminopropane or N-oleyldipropylenetriamine.
- Carboxylic acids are phthalic acid, isophthalic acid, terephthalic acid, naphthalenedicarboxylic acid, ethylenediaminetetraacetic acid and cyclohexanedicarboxylic acid.
- amine salt type polar nitrogen compounds contained in the mineral oil as other additive components are N-methyl triethanolammonium distearyl ester chloride and N-methyltriethanolammonium distearyl ester methosulfate.
- C 7 -C 30 -alcohols which may be contained as further additive components in the mineral oil are dodecanol, stearyl alcohol and ceryl alcohol.
- polyalkylene glycols which may be contained as further additive components in the mineral oil are polyethylene glycols, polypropylene glycols and ethylene oxide-propylene oxide copolymers having molecular weights of from 500 to 5,000.
- esters of polyoxyalkylene compounds which may be present as further additive components in the mineral oil are C 10 -C 24 monoalkyl ester or dialkyl esters of polyalkylene glycols such as polyethylene glycol monostearyl ester or polypropylene glycol dioleate.
- ethers of polyoxyalkylene compounds which may be contained as further additive components in the mineral oil are C 1 -C 4 monoalkyl ethers or dialkyl ethers of polyalkylene glycols such as polyethylene glycol monomethyl ether or polypropylene glycol dibutyl ether.
- hydrocarbon polymers which may be included as further additive components in the mineral oil are copolymers of ethylene and C 3 -C 20 ⁇ -olefins such as ethylene-propylene copolymers or ethylene-dodecene copolymers or hydrogenated polymers of hydrogenated polyunsaturated monomers Diene copolymers such as hydrogenated polybutadiene or hydrogenated polyisoprene with molecular weight numbers up to 30,000.
- alkylphenol-aldehyde copolymers which may be included as further additive components in the mineral oil are copolymers which can be prepared by reacting alkylated phenols such as phenol-propylene oligomer adducts with paraformaldehyde.
- aromatic compounds having C 8 -C 100 -alkyl substituents which may be contained as further additive components in the mineral oil are compounds which can be prepared by Friedel-Kraft condensation of halogenated hydrocarbons such as halogenated polyethylene wax with aromatic hydrocarbons such as benzene or naphthalene.
- detergents which may be present as further additive components in the mineral oil are aliphatic sulfonic acids such as C 8 -C 30 -alkanesulfonates or aromatic-aliphatic alkanesulfonates, in particular nonylbenzenesulfonic acid, dodecylbenzenesulfonic acid, didodecylbenzenesulfonic acid and nonylnaphthalenesulfonic acid.
- aliphatic sulfonic acids such as C 8 -C 30 -alkanesulfonates or aromatic-aliphatic alkanesulfonates, in particular nonylbenzenesulfonic acid, dodecylbenzenesulfonic acid, didodecylbenzenesulfonic acid and nonylnaphthalenesulfonic acid.
- demulsifiers which may be present as further additive components in the mineral oil are oxalkylated phenol-formaldehyde condensates, polyalkylene glycol-modified diglycidyl ethers, polyesteramines or alkoxylated fatty acids.
- cetane improvers which may be present as further additive components in the mineral oil are organic nitric acid esters such as ethylhexyl nitrate, cyclohexyl nitrate or ethoxyethyl nitrate, or soluble organic peroxides, hydroperoxides or peresters.
- Preferred defoamers which may be contained as further additive components in the mineral oil, are polyalkylene oxide-siloxane block copolymers and carboxylated polyamines.
- polyalkylene oxide-siloxane block copolymers are block copolymers containing a combination of trifunctional siloxane blocks such as monomethylsiloxane groups, difunctional siloxane groups such as dimethylsiloxane groups and monofunctional siloxane groups such as trimethylsiloxane groups; a preferred length of the siloxane blocks is 5 to 20 monomer units.
- the preferred length is 2 to 40 monomer units, preferably polyoxyalkylene blocks of ethylene oxide and / or propylene oxide units.
- carboxylated polyamines as defoamers are reaction products of C 8 -C 24 -fatty acids and amines such as ethylenediamine, butylenediamine, diethylenetriamine and pentaethylenehexamine-1,2-diaminobutanol.
- cosolvents which may be included as additional additive components in the mineral oil compositions are gasoline fractions, toluene, xylene, ethylbenzene, isononanol, ethylhexanol, dodecylphenol, epoxidized rapeseed oil and epoxidized soybean oil.
- the formulations of mineral oil as the main component and small proportions of an additive mixture are preferably suitable as flowable media to be transported at low temperatures and suitable as a mineral oil fuel with high lubricity and flowability.
- Examples of the flowable media to be transported at low temperatures are the transport of crude oil formulations from the crude oil production facility through pipelines for loading, storage and transport of diesel or heating oil formulations in pipelines.
- Lubricity test (corrected "wear scar diameter” at 60 ° C) according to ISO 12156-1
- a 500 ml sample is stored in a graduated cylinder for 16 h and then the 80% by volume of the sample present above is filtered off with suction and discarded. The remaining 20% by volume of the sample (100 ml) are homogenized at 40 ° C. and the cloud point (CP) according to DIN EN 23 015 is determined therefrom.
- a 500 ml mineral oil sample is shaken 20 x vertically, tempered for 16 h at 10 ° C, shaken 10 x vertically, and the entire sample is at once through a filter made of cellulose nitrate (diameter 50 mm, pore size 0.8 .mu.m), on a Suction cup with a vacuum of approx. 200 hPa is added, filtered. The time (s) in which the sample passes through the filter is determined. The SEDAB filtration test is passed if the sample passes the filter for a period ⁇ 120 s.
- Styrene-maleic anhydride copolymer partially modified with C 16 -C 18 fatty amine, number average molecular weight 9500 g / mol, acid number 29
- the additive solution according to 1.2 is injected at 0.48 kg / min into a product stream of diesel fuel additive 16080601 at 800 kg / min and transferred to a storage tank.
- the testing of the cold resistance of the mineral oil formulation results in a CFPP value of -10 ° C.
- the Lubricity test gives a wear scar diameter of 395 ⁇ m.
- the CFPP value is -3 ° C. and the wear scar diameter is 520 ⁇ m.
- Styrene-maleic anhydride copolymer partially modified with C 16 -C 18 fatty amine, number average molecular weight 21000 g / mol, acid number 37
- Vinyl acetate-ethylhexyl acrylate copolymer (molar ratio 1.5: 1, number average molecular weight 13500)
- the additive solution according to 2.2 is injected at 0.12 kg / min and transferred to a storage tank.
- the testing of the cold resistance of the mineral oil formulation results in a CFPP value of -10 ° C.
- the lubricity test gives a wear scar diameter of 387 ⁇ m.
- the CFPP value is -5 ° C. and the wear scar diameter is 528 ⁇ m.
- Styrene-maleic anhydride copolymer partially modified with C 16 -C 18 fatty amine, number average molecular weight 9500 g / mol, acid number 25
- the additive solution according to 3.2 is injected at 0.24 kg / min into a product stream of non-additive fuel oil batch 030225 at 800 kg / min and transferred to a storage tank.
- the CFPP value is -13 ° C.
- the additive solution according to 4.2 is injected at 0.28 kg / min and transferred to a storage tank.
- the CFPP value is -1 ° C.
- Octadecyl acrylate-ethyl acrylate copolymer (molar ratio 4: 1, number average molecular weight 13500)
- the additive solution according to 5.2 is injected at 0.48 kg / min into a product stream of diesel fuel additive 16080601 at 800 kg / min and transferred to a storage tank.
- the testing of the cold resistance of the mineral oil formulation results in a CFPP value of -17 ° C.
- the CP value of the short-term sediment test is + 6 ° C.
- the SEDAB filtration test is passed (500 ml in 75 s).
- the CFPP value is -3 ° C.
- the CP value of the short-term sediment test is + 10 ° C.
- the SEDAB filtration test is considered failed (468 ml in> 120 s).
- Octadecene-maleic anhydride copolymer partially-imidized with C 16 -C 18 -fatty amine, acid number 40, number-average molecular weight 4200 g / mol,
- the additive solution according to 6.2 is injected at 0.24 kg / min and transferred to a storage tank.
- the additive solution according to 7.2 is injected at 0.24 kg / min and transferred to a storage tank.
- the CFPP value is -13 ° C.
- the CFPP value is -3 ° C.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2003149864 DE10349864B4 (de) | 2003-10-22 | 2003-10-22 | Additivmischung als Bestandteil einer Mineralölrezeptur |
DE2003149865 DE10349865B4 (de) | 2003-10-22 | 2003-10-22 | Additivmischung als Bestandteil einer Rezeptur aus Mineralöl |
PCT/DE2004/002314 WO2005040315A1 (de) | 2003-10-22 | 2004-10-15 | Additivmischung als bestandteil einer rezeptur aus mineralöl |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1685216A1 EP1685216A1 (de) | 2006-08-02 |
EP1685216B1 true EP1685216B1 (de) | 2013-01-30 |
Family
ID=34524053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04790006A Not-in-force EP1685216B1 (de) | 2003-10-22 | 2004-10-15 | Rezeptur aus Mineralöl und einer Additivmischung |
Country Status (8)
Country | Link |
---|---|
US (1) | US7776801B2 (ru) |
EP (1) | EP1685216B1 (ru) |
JP (1) | JP4991302B2 (ru) |
KR (1) | KR100749220B1 (ru) |
CA (1) | CA2542935C (ru) |
EA (1) | EA011358B1 (ru) |
ES (1) | ES2402928T3 (ru) |
WO (1) | WO2005040315A1 (ru) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009085552A2 (en) * | 2007-12-20 | 2009-07-09 | Dow Global Technologies Inc. | Improved corrosion and microbial control in hydrocarbonaceous compositions |
US8546386B2 (en) * | 2008-05-15 | 2013-10-01 | Dow Global Technologies Llc | Corrosion and microbial control in hydrocarbonaceous compositions |
CN101544735B (zh) * | 2009-04-10 | 2011-12-28 | 华东理工大学 | 一种三元梳型共聚物及其制备方法和应用 |
US8632638B2 (en) * | 2010-11-19 | 2014-01-21 | Chevron Oronite Company Llc | Method for cleaning deposits from an engine fuel delivery system |
JP2018090652A (ja) * | 2015-04-09 | 2018-06-14 | 株式会社クラレ | 原油分散安定剤 |
CN108997521A (zh) * | 2018-06-20 | 2018-12-14 | 深圳市广昌达石油添加剂有限公司 | 一种用作原油降凝降粘剂的多元共聚物及其制备方法 |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2922768A (en) * | 1956-04-12 | 1960-01-26 | Mino Guido | Process for polymerization of a vinylidene monomer in the presence of a ceric salt and an organic reducing agent |
US3287273A (en) * | 1965-09-09 | 1966-11-22 | Exxon Research Engineering Co | Lubricity additive-hydrogenated dicarboxylic acid and a glycol |
US3584078A (en) * | 1966-07-11 | 1971-06-08 | Union Carbide Corp | Polyvinyl esters and derivatives therefrom |
JPS6017476B2 (ja) * | 1982-09-20 | 1985-05-02 | 日本合成化学工業株式会社 | 石油類用低温流動性改善剤 |
DE3405843A1 (de) * | 1984-02-17 | 1985-08-29 | Bayer Ag, 5090 Leverkusen | Copolymere auf basis von maleinsaeureanhydrid und (alpha), (beta)-ungesaettigten verbindungen, ein verfahren zu ihrer herstellung und ihre verwendung als paraffininhibitoren |
US4726811A (en) * | 1986-02-24 | 1988-02-23 | Pony Industries, Inc. | Hydrocarbon oils with improved pour points |
DE3621395A1 (de) * | 1986-06-26 | 1988-01-28 | Ruhrchemie Ag | Verfahren zur verbesserung der fliessfaehigkeit von mineraloelen und mineraloeldestillaten |
DE3725059A1 (de) * | 1987-07-29 | 1989-02-09 | Roehm Gmbh | Polymere fliessverbesserer fuer mitteldestillate |
DD295507A7 (de) | 1987-08-10 | 1991-11-07 | Buna Ag | Verfahren zur herstellung neuer halbacetale von ethen-vinylacetat-vinylalkoholcopolymeren mit butyraldehyd |
DE3742630A1 (de) * | 1987-12-16 | 1989-06-29 | Hoechst Ag | Polymermischungen fuer die verbesserung der fliessfaehigkeit von mineraloeldestillaten in der kaelte |
DE3905681A1 (de) * | 1989-02-24 | 1990-08-30 | Basf Ag | Konzentrierte mischungen von pfropfcopolymerisaten aus estern von ungesaettigten saeuren und ethylen-vinylester-copolymerisaten |
DD282462A5 (de) | 1989-04-24 | 1990-09-12 | Leuna Werke Veb | Verfahren zur herstellung trennmittelfreier nichtblockender ethylen-vinylacetat-copolymerer |
DD293125B5 (de) | 1990-03-26 | 1995-10-19 | Leuna Werke Gmbh | Verfahren zur Herstellung modifizierter Ethylen-Vinylacetat-Copolymerwachse |
DE4036227A1 (de) * | 1990-11-14 | 1992-05-21 | Basf Ag | Erdoelmitteldestillate mit verbesserten fliesseigenschaften in der kaelte |
GB9200694D0 (en) | 1992-01-14 | 1992-03-11 | Exxon Chemical Patents Inc | Additives and fuel compositions |
GB9222458D0 (en) | 1992-10-26 | 1992-12-09 | Exxon Chemical Patents Inc | Oil additives and compositions |
GB9411614D0 (en) | 1994-06-09 | 1994-08-03 | Exxon Chemical Patents Inc | Fuel oil compositions |
ATE203558T1 (de) | 1994-05-30 | 2001-08-15 | Hitachi Chemical Co Ltd | Schutzfilm für anstrichfilm |
CA2182993C (en) * | 1994-12-13 | 2001-08-07 | Brian William Davies | Fuel oil compositions |
JPH09184830A (ja) | 1995-12-28 | 1997-07-15 | Daicel Chem Ind Ltd | 充填剤充填装置、充填剤の充填方法および充填剤充填カラム集合体 |
ATE223953T1 (de) * | 1997-01-07 | 2002-09-15 | Clariant Gmbh | Verbesserung der fliessfähigkeit von mineralölen und mineralöldestillaten unter verwendung von alkylphenol-aldehydharzen |
US6495495B1 (en) * | 1999-08-20 | 2002-12-17 | The Lubrizol Corporation | Filterability improver |
EP1088880A1 (en) * | 1999-09-10 | 2001-04-04 | Fina Research S.A. | Fuel composition |
DE10155747B4 (de) * | 2001-11-14 | 2008-09-11 | Clariant Produkte (Deutschland) Gmbh | Additive für schwefelarme Mineralöldestillate, umfassend einen Ester eines alkoxylierten Polyols und ein Alkylphenol-Aldehydharz |
DE10155774B4 (de) * | 2001-11-14 | 2020-07-02 | Clariant Produkte (Deutschland) Gmbh | Additive für schwefelarme Mineralöldestillate, umfassend einen Ester alkoxylierten Glycerins und einen polaren stickstoffhaltigen Paraffindispergator |
ES2317082T3 (es) * | 2003-10-22 | 2009-04-16 | Innospec Leuna Gmbh | Composiciones a base de aceite mineral y de una mezcla de aditivos. |
-
2004
- 2004-10-15 EA EA200600804A patent/EA011358B1/ru not_active IP Right Cessation
- 2004-10-15 JP JP2006535936A patent/JP4991302B2/ja not_active Expired - Fee Related
- 2004-10-15 US US10/577,006 patent/US7776801B2/en not_active Expired - Fee Related
- 2004-10-15 KR KR1020067007765A patent/KR100749220B1/ko not_active IP Right Cessation
- 2004-10-15 CA CA002542935A patent/CA2542935C/en not_active Expired - Fee Related
- 2004-10-15 ES ES04790006T patent/ES2402928T3/es active Active
- 2004-10-15 EP EP04790006A patent/EP1685216B1/de not_active Not-in-force
- 2004-10-15 WO PCT/DE2004/002314 patent/WO2005040315A1/de active Application Filing
Also Published As
Publication number | Publication date |
---|---|
US7776801B2 (en) | 2010-08-17 |
KR100749220B1 (ko) | 2007-08-13 |
ES2402928T3 (es) | 2013-05-10 |
EA011358B1 (ru) | 2009-02-27 |
KR20060090252A (ko) | 2006-08-10 |
EP1685216A1 (de) | 2006-08-02 |
CA2542935C (en) | 2009-11-10 |
JP4991302B2 (ja) | 2012-08-01 |
CA2542935A1 (en) | 2005-05-06 |
JP2007509210A (ja) | 2007-04-12 |
US20070219100A1 (en) | 2007-09-20 |
EA200600804A1 (ru) | 2006-10-27 |
WO2005040315A1 (de) | 2005-05-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE10000649C2 (de) | Mehrfunktionelles Additiv für Brennstofföle | |
EP0900836A1 (de) | Additiv zur Verbesserung der Fliessfähigkeit von Mineralölen und Mineralöldestillaten | |
EP1022293B1 (de) | Copolymere und ihre Verwendung als Additiv zur Verbesserung der Kaltfliesseigenschaften von Mitteldestillaten | |
WO1997046640A1 (de) | Paraffindispergatoren für erdölmitteldestillate | |
EP1685216B1 (de) | Rezeptur aus Mineralöl und einer Additivmischung | |
EP0997517A1 (de) | Polymermischungen zur Verbesserung der Schmierwirkung von Mitteldestillaten | |
EP1194456B1 (de) | Hydroxylgruppenhaltige copolymere und ihre verwendung zur herstellung von brennstoffölen mit verbesserter schmierwirkung | |
EP1675932B1 (de) | Zusammensetzungen aus Mineralöl und einer Additivmischung | |
EP1675881B1 (de) | Additiv als bestandteil von minerallzusammensetzungen | |
EP0937108B1 (de) | Co- und terpolymere auf basis von alpha,beta-ungesättigten verbindungen und alpha,beta-ungesättigten dicarbonsäureanhydriden | |
DE10349859B4 (de) | Additivmischung als Bestandteil von Mineralölzusammensetzungen | |
DE10349865B4 (de) | Additivmischung als Bestandteil einer Rezeptur aus Mineralöl | |
DE10349861B4 (de) | Additivmischung als Bestandteil von Zusammensetzungen aus Mineralöl | |
DE10349860B4 (de) | Additivmischungen als Bestandteil von Mineralölrezepturen | |
DE10349864B4 (de) | Additivmischung als Bestandteil einer Mineralölrezeptur | |
DE10349858B4 (de) | Additiv als Bestandteil von additivierten Mineralölen | |
DE10349862B4 (de) | Additiv als Bestandteil von Mineralölzusammensetzungen | |
DE10000650C2 (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 |
|
17P | Request for examination filed |
Effective date: 20060421 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: MEYER, TORSTEN Inventor name: BRAUER, ERHARD Inventor name: TAEUBERT, HILTRUD Inventor name: HAUBOLD, WOLFGANG Inventor name: VON DER WENSE, DIETRICH |
|
DAX | Request for extension of the european patent (deleted) | ||
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: INNOSPEC LEUNA GMBH |
|
17Q | First examination report despatched |
Effective date: 20090519 |
|
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 1/236 20060101ALI20120727BHEP Ipc: C10L 10/08 20060101ALI20120727BHEP Ipc: C10L 1/14 20060101AFI20120727BHEP Ipc: C10L 1/195 20060101ALI20120727BHEP Ipc: C10L 1/19 20060101ALI20120727BHEP Ipc: C10L 1/197 20060101ALI20120727BHEP |
|
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): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D Free format text: NOT ENGLISH |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP Ref country code: AT Ref legal event code: REF Ref document number: 595719 Country of ref document: AT Kind code of ref document: T Effective date: 20130215 |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D Free format text: LANGUAGE OF EP DOCUMENT: GERMAN |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 502004014012 Country of ref document: DE Effective date: 20130328 |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2402928 Country of ref document: ES Kind code of ref document: T3 Effective date: 20130510 |
|
REG | Reference to a national code |
Ref country code: NL Ref legal event code: VDEP Effective date: 20130130 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130430 Ref country code: CY Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 |
|
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 FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130530 Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 Ref country code: PL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130501 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: EE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 Ref country code: DK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 Ref country code: RO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 Ref country code: CZ Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 |
|
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 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 |
|
26N | No opposition filed |
Effective date: 20131031 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20131018 Year of fee payment: 10 Ref country code: GB Payment date: 20131022 Year of fee payment: 10 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R097 Ref document number: 502004014012 Country of ref document: DE Effective date: 20131031 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: ES Payment date: 20131022 Year of fee payment: 10 |
|
BERE | Be: lapsed |
Owner name: INNOSPEC LEUNA G.M.B.H. Effective date: 20131031 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: MM4A |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20131031 Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20131031 |
|
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: 20131031 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20131015 |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: MM01 Ref document number: 595719 Country of ref document: AT Kind code of ref document: T Effective date: 20131015 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20131015 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20141015 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: TR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20130130 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20131015 Ref country code: HU Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO Effective date: 20041015 Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20141015 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST Effective date: 20150630 |
|
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: 20141031 |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FD2A Effective date: 20160105 |
|
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: 20141016 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 20161014 Year of fee payment: 13 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R119 Ref document number: 502004014012 Country of ref document: DE |
|
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: 20180501 |