EP0915944B1 - Use of an additive for the improvement of lubricating properties of a fuel with low sulphur content for diesel engines - Google Patents
Use of an additive for the improvement of lubricating properties of a fuel with low sulphur content for diesel engines Download PDFInfo
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- EP0915944B1 EP0915944B1 EP97935651A EP97935651A EP0915944B1 EP 0915944 B1 EP0915944 B1 EP 0915944B1 EP 97935651 A EP97935651 A EP 97935651A EP 97935651 A EP97935651 A EP 97935651A EP 0915944 B1 EP0915944 B1 EP 0915944B1
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
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- 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
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- 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
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- 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
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- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
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- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/188—Carboxylic acids; metal salts thereof
- C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
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- 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
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- 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
- C10L1/1886—Carboxylic acids; metal salts thereof naphthenic acid
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—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
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- 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
- C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
- C10L1/2286—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen triple bonds, e.g. nitriles
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- 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
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
Definitions
- the present invention relates to a fuel containing a creaminess additive to improve lubricating properties of fuels, whether diesel or aviation fuel (jet fuel), and more particularly of low-content diesel fuels in sulfur.
- additives containing dimer acids such as those containing trimer acids, cannot be used in fuels for vehicles in which the fuel may come into contact with lubrication because these acids form by chemical reaction deposits that are sometimes insoluble in oil, but above all incompatible with commonly used detergents.
- US Patent 4,609,376 recommends the use anti-wear additives obtained from acid esters mono- and poly-carboxylic and polyhydric alcohols in fuels containing alcohols in their composition.
- US Patent 2,686,713 recommends the introduction of tall oil up to 60 ppm in diesel fuels to prevent rust from forming on surfaces metal in contact with these fuels.
- esters vegetable oils or the vegetable oils themselves in these fuels are also chosen route.
- esters vegetable oils or the vegetable oils themselves in these fuels are also chosen route.
- One of the major drawbacks of these esters is their low lubricity at a concentration of less than 0.5% by weight in fuels.
- patent application WO 95/33805 recommends the introduction of a cold-keeping additive consisting of nitrogenous additives comprising one or more NR 13 groups in which R 13 comprises from 12 to 24 atoms carbon, is linear, slightly branched or alicyclic and aromatic, the nitrogen group which can be linked by CO or CO 2 and form amine carboxylates or amides.
- FR-A-1388295 describes a process for incorporating solids in a liquid as well as liquids as well obtained.
- the carrier organic liquid can be diesel but this liquid is never used alone.
- Such a liquid is not suitable as "diesel engine fuel”; he there is no mention of diesel oil lubrication.
- Patent US2907646 describes the use of tall oil in combination with an imidazoline as an anti-rust additive in fuels. There is no mention of the content of diesel fuel sulfur if not enough to be likely to react), or the lubricating effect of tall oil.
- the present invention aims to solve the problems encountered with the additives proposed by the prior art, that is to say to improve the lubricating power of desulfurized and flavored fuels, while remaining compatible with other additives, especially detergents, and lubricating oils, especially forming no deposits and reducing the cost, in particular by a lower additive content, well below 0.5%.
- the invention therefore provides a use, for improve the lubricating properties of diesel fuels low sulfur, oiliness additive consisting of a combination of at least one hydrocarbon aliphatic monocarboxylic, saturated or unsaturated, of chain linear between 12 and 24 carbon atoms, and at minus one polycyclic hydrocarbon compound selected from the group consisting of the natural resin acids obtained from the distillation residues of natural oils extracted from coniferous trees, especially conifers resinous, and derivatives amine carboxylates, esters and nitriles of these acids.
- the polycyclic hydrocarbon compound is chosen from the group consisting of the natural resin acids obtained from the distillation residues of natural oils extracted from coniferous trees, especially conifers resinous, as well as amine carboxylates, esters and the nitriles of these acids.
- the acid is preferred. abietic, dihydroabietic acid, acid tetrahydroabietic, dehydroabietic acid, acid neoabietic, pimaric acid, levopimaric acid and parastrinic acid and their derivatives.
- the aliphatic hydrocarbon monocarboxylic is in the form of acid, carboxylate amines and esters.
- the combination comprises from 1 to 50% by weight of at least one polycyclic hydrocarbon compound, and from 50 to 99% by weight of at least one acid linear monocarboxylic, saturated or unsaturated, comprising 12 to 24 carbon atoms, these products being present under form of acid, carboxylate of amines or esters.
- amine carboxylates By amine carboxylates is meant the compounds resulting from the reaction of these acids with amines or primary, secondary and tertiary polyamines including from 1 to 8 carbon atoms per chain and the alkylene amines and primary, secondary or tertiary alkylene polyamines comprising from 2 to 8 carbon atoms.
- these amine salts are derived from selected amines in the group consisting of ethyl-2-hexylamine, N, N-dibutylamine, ethylenediamine, diethylenetriamine and tetraethylenepentamine.
- alkanol esters are preferred primary with 1 to 8 carbon atoms or polyalcohols from the group consisting of ethylene glycol, propylene glycol, glycerol, trimethylolpropane, pentaerythritol, diethanolamine, triethanolamine and their derivatives.
- the fuel contains 50 to 1000 ppm of the oiliness additive.
- additives usually added in such fuels such as detergent additives, additives improving the index of cetane, demulsifying additives, anti-corrosion additives, additives improving cold resistance, and odor modifying additives.
- This example describes the choice of additives in function of their solubility in a weak diesel sulfur.
- Each additive in test is diluted to 5% by weight in a diesel (GO) at 500 ppm sulfur, at room temperature.
- additives according to the invention are designated by Y and by C the comparative examples in Table I below.
- Additives Y consist, on the one hand, of a mixture of a combination of fatty acids containing by weight 50 to 55% oleic acid, 30 to 40% linoleic acid, 3 to 5% palmitic acid and 1 with 2% linolenic acid, and for another part in resin acids obtained by distillation of tall oil, by-product of the manufacture of wood pulp by the sulphate process.
- C 1 corresponds to pure oleic acid
- C 2 to rosin which is a mixture of resin acids corresponding to the distillation residue of pine gems
- C 3 is a mixture of dimer acids obtained by thermal dimerization and / or catalytic of unsaturated fatty acids.
- the test consists in imposing jointly with a ball of steel in contact with a stationary metal plate, a pressure corresponding to a weight of 200 g and a displacement alternating 1 mm at a frequency of 50 Hz.
- the ball in movement is lubricated by the composition to be tested.
- the temperature is maintained at 60 ° C for the duration of the test, i.e. 75 min.
- the lubricity is expressed as the average value of the footprint diameters wear of the ball on the plate.
- a small diameter wear generally less than 400 ⁇ m indicates good lubricity; conversely, a wear diameter important (greater than 400 ⁇ m) translates a power of as much more insufficient than the value of the wear diameter is high.
- Example I studies the compatibility of additives described in Example I with lubricants usually used in diesel engines according to the protocol described below.
- the additives of the invention, Y 1 and Y 2 give no deposit or cloudiness when the diesel fuel with 100 ppm additive is added to the oil.
- the purpose of this example is to describe additives oiliness adapted to be introduced into fuels according to the invention.
- amine carboxylates obtained by simple mixing at room temperature and at atmospheric pressure of Y 1 with an amine or polyamine according to the invention, thus allowing the neutralization of the carboxylic sites.
Abstract
Description
La présente invention concerne un carburant contenant un additif d'onctuosité pour améliorer les propriétés lubrifiantes des carburants, qu'il s'agisse de carburant diesel ou de carburant aviation (jet fuel), et plus particulièrement de carburants diesels à faible teneur en soufre.The present invention relates to a fuel containing a creaminess additive to improve lubricating properties of fuels, whether diesel or aviation fuel (jet fuel), and more particularly of low-content diesel fuels in sulfur.
Il est bien connu que les carburants diesels et les carburants aviations doivent posséder des aptitudes à la lubrification pour la protection des pompes, des systèmes d'injection et de toutes les parties en mouvement avec lesquels ces produits entrent en contact dans un moteur à combustion interne. Avec la volonté d'utiliser des produits de plus en plus purs et non polluants, notamment dépourvus de soufre, l'industrie du raffinage a été amenée à perfectionner de plus en plus ses procédés de traitement d'élimination des composés du soufre. Cependant on a observé qu'en perdant les composés soufrés on perdait également les composés aromatiques et polaires souvent associés, ce qui occasionnait une perte du pouvoir lubrifiant de ces carburants. Ainsi, en deçà de certaines teneurs, la suppression de composés soufrés dans la composition de ces produits favorise très sensiblement les phénomènes d'usure et de rupture de pièces en mouvement au niveau des pompes et des systèmes d'injection. Comme la réglementation de nombreux pays a imposé de limiter la teneur supérieure acceptable en composés soufrés dans les carburants à 0,05% en poids pour diminuer les émissions des voitures, camions ou autobus en gaz de combustion polluants, notamment dans les agglomérations urbaines, il est nécessaire de remplacer ces composés lubrifiants par d'autres composés non polluants au regard de l'environnement mais présentant un pouvoir lubrifiant suffisant pour éviter les risques d'usure. It is well known that diesel fuels and aviation fuels must have skills in lubrication for the protection of pumps, systems injection and all moving parts with which these products come into contact with in a internal combustion. With the desire to use products increasingly pure and non-polluting, especially devoid of sulfur, the refining industry was brought to improving their treatment processes more and more removal of sulfur compounds. However we observed that by losing the sulfur compounds we also lost the aromatic and polar compounds often associated, which caused a loss of the lubricating power of these fuels. Thus, below certain levels, the removal of sulfur compounds in the composition of these products very significantly promotes wear phenomena and rupture of moving parts at the pumps and injection systems. As the regulation of many countries imposed to limit the upper content acceptable as sulfur compounds in fuels at 0.05% by weight to reduce emissions from cars, trucks or buses with polluting combustion gases, particularly in urban agglomerations, it is necessary to replace these lubricating compounds by other non-polluting compounds with regard to the environment but presenting a power sufficient lubricant to avoid the risk of wear.
Pour résoudre ce problème, plusieurs types d'additifs ont déjà été proposés. Ainsi, on a ajouté aux gazoles des additifs anti-usures, connus pour certains dans le domaine des lubrifiants, du type des esters d'acides gras et des acides gras dimères non saturés, des amines aliphatiques, des esters d'acides gras et de diéthanolamine et des acides monocarboxyliques aliphatiques à chaíne longue tels que décrits dans les brevets US 2.252.889, US 4.185.594, US 4.204.481, US 4.208.190, US 4.428.182. La plupart de ces additifs présente un pouvoir lubrifiant suffisant mais à des concentrations bien trop élevées ce qui est très défavorable économiquement à l'achat. En outre, les additifs contenant des acides dimères, comme ceux contenant des acides trimères, ne peuvent être utilisés dans les carburants alimentant les véhicules dans lesquels le carburant peut être en contact avec l'huile de lubrification, car ces acides forment par réaction chimique des dépôts parfois insolubles dans l'huile, mais surtout incompatibles avec les détergents usuellement utilisés.To solve this problem, several types additives have already been proposed. So we added to diesel fuel additives anti-wear, known for some in the field of lubricants, of the fatty acid ester type and unsaturated dimer fatty acids, amines aliphatics, esters of fatty acids and diethanolamine and long chain aliphatic monocarboxylic acids as described in US Patents 2,252,889, US 4,185,594, US 4,204,481, US 4,208,190, US 4,428,182. The most of these additives have a lubricating power sufficient but at concentrations too high which is very economically unfavorable to purchase. In addition, additives containing dimer acids, such as those containing trimer acids, cannot be used in fuels for vehicles in which the fuel may come into contact with lubrication because these acids form by chemical reaction deposits that are sometimes insoluble in oil, but above all incompatible with commonly used detergents.
Le brevet US 4.609.376 préconise l'utilisation d'additifs anti-usures obtenus à partir d'esters d'acides mono- et poly-carboxyliques et d'alcools polyhydroxylés dans les carburants contenant des alcools dans leur composition.US Patent 4,609,376 recommends the use anti-wear additives obtained from acid esters mono- and poly-carboxylic and polyhydric alcohols in fuels containing alcohols in their composition.
Le brevet US 2.686.713 préconise l'introduction de tall oil jusqu'à 60 ppm dans les carburants diesel afin de prévenir la formation de rouille sur les surfaces métalliques en contact avec ces carburants.US Patent 2,686,713 recommends the introduction of tall oil up to 60 ppm in diesel fuels to prevent rust from forming on surfaces metal in contact with these fuels.
Une autre voie choisie est d'introduire des esters d'huiles végétales ou les huiles végétales elles-mêmes dans ces carburants pour améliorer leur pouvoir lubrifiant ou leur onctuosité. Parmi ceux-ci, on trouve les esters dérivés d'huiles de colza, de lin, de soja, de tournesol ou les huiles elles-mêmes (voir brevets EP 635.558 et EP 605.857). Un des inconvénients majeurs de ces esters est leur faible pouvoir lubrifiant à une concentration inférieure à 0,5 % en poids dans les carburants.Another chosen route is to introduce esters vegetable oils or the vegetable oils themselves in these fuels to improve their lubricity or their smoothness. Among these are derivative esters rapeseed, linseed, soybean, sunflower or oils themselves (see patents EP 635,558 and EP 605,857). One of the major drawbacks of these esters is their low lubricity at a concentration of less than 0.5% by weight in fuels.
Pour améliorer le pouvoir lubrifiant des gazoles, la demande de brevet WO 95/33805 préconise l'introduction d'un additif de tenue à froid constitué par des additifs azotés comprenant un à plusieurs groupements N-R13 dans lequel R13 comprend de 12 à 24 atomes de carbone, est linéaire, légèrement ramifié ou alicyclique et aromatique le groupement azoté pouvant être relié par CO ou CO2 et former des carboxylates d'amines ou des amides.To improve the lubricating power of gas oils, patent application WO 95/33805 recommends the introduction of a cold-keeping additive consisting of nitrogenous additives comprising one or more NR 13 groups in which R 13 comprises from 12 to 24 atoms carbon, is linear, slightly branched or alicyclic and aromatic, the nitrogen group which can be linked by CO or CO 2 and form amine carboxylates or amides.
FR-A-1388295 décrit un procédé d'incorporation de solides dans un liquide, ainsi que les liquides ainsi obtenus. Le liquide organique porteur peut être du gazole mais ce liquide n'est jamais utilisé seul. Un tel liquide n'est pas adapté comme "carburant pour moteur diesel"; il n'y aucune mention de la lubrifiance des gazoles.FR-A-1388295 describes a process for incorporating solids in a liquid as well as liquids as well obtained. The carrier organic liquid can be diesel but this liquid is never used alone. Such a liquid is not suitable as "diesel engine fuel"; he there is no mention of diesel oil lubrication.
Le brevet US2658823 décrit l'utilisation d'un sel de tall oil comme additif anti-sédimentation dans les carburants. Il n'y a aucune mention de la teneur en soufre du gazole ni de l'effet de lubrifiance du tall oil.The patent US2658823 describes the use of a salt of tall oil as an anti-sedimentation additive in fuels. There is no mention of the sulfur content diesel oil or the lubricating effect of tall oil.
Le brevet US2907646 décrit l'utilisation de tall oil en combinaison avec une imidazoline comme additif anti-rouille dans les carburants. Il n'y a aucune mention de la teneur en soufre du gazole si ce n'est une quantité suffisante pour être susceptible de réagir), ni de l'effet de lubrifiance du tall oil.Patent US2907646 describes the use of tall oil in combination with an imidazoline as an anti-rust additive in fuels. There is no mention of the content of diesel fuel sulfur if not enough to be likely to react), or the lubricating effect of tall oil.
Le brevet US2686713 décrit l'utilisation de tall oil comme additif anti-rouille dans les carburants. Il n'y a aucune mention de la teneur en soufre du gazole ni de l'effet de lubrifiance du tall oil. La teneur en tall oil dans le cas d'un gazole est nécessairement au plus de 60ppm.US Pat. No. 2,686,713 describes the use of tall oil as an anti-rust additive in fuels. There is no mention of the sulfur content of diesel or the lubricating effect of tall oil. Tall oil content in the case of a diesel fuel is necessarily at most 60ppm.
Le brevet US3667152 (correspondant du DE2022585) décrit l'utilisation de l'acide de tall oil (tall oil fatty acid) comme additif anti-usure, séparation de l'eau et stabilité thermique. Cependant, ce document indique que le tall oil en tant que tel n'est pas approprié.The patent US3667152 (corresponding to DE2022585) describes the use of tall oil fatty acid as an anti-wear additive, water separation and stability thermal. However, this document indicates that tall oil in as long as it is not appropriate.
La présente invention vise à résoudre les problèmes rencontrés avec les additifs proposés par l'art antérieur, c'est-à-dire à améliorer le pouvoir lubrifiant des carburants désulfurés et désaromatisés, tout en restant compatibles avec les autres additifs, notamment les détergents, et les huiles lubrifiantes, notamment en ne formant pas de dépôts et en diminuant le coût notamment par une teneur moindre en additif, nettement inférieure à 0,5%. The present invention aims to solve the problems encountered with the additives proposed by the prior art, that is to say to improve the lubricating power of desulfurized and flavored fuels, while remaining compatible with other additives, especially detergents, and lubricating oils, especially forming no deposits and reducing the cost, in particular by a lower additive content, well below 0.5%.
L'invention fournit donc une utilisation, pour améliorer les propriétés lubrifiantes de carburants diesels à faible teneur en soufre, d'un additif d'onctuosité constitué par une combinaison d'au moins un hydrocarbure aliphatique monocarboxylique, saturé ou insaturé, de chaíne linéaire comprise entre 12 et 24 atomes de carbone, et au moins un composé hydrocarboné polycyclique choisi dans le groupe constitué par les acides résiniques naturels obtenus à partir des résidus de distillation des huiles naturelles extraites des arbres résineux, notamment des conifères résineux, et les dérivés les carboxylates d'amines, esters et nitriles de ces acides.The invention therefore provides a use, for improve the lubricating properties of diesel fuels low sulfur, oiliness additive consisting of a combination of at least one hydrocarbon aliphatic monocarboxylic, saturated or unsaturated, of chain linear between 12 and 24 carbon atoms, and at minus one polycyclic hydrocarbon compound selected from the group consisting of the natural resin acids obtained from the distillation residues of natural oils extracted from coniferous trees, especially conifers resinous, and derivatives amine carboxylates, esters and nitriles of these acids.
Des modes de réalisation particuliers font l'objet des revendications 2 à 11. Particular embodiments are the subject of claims 2 to 11.
On s'est aperçu que le pouvoir lubrifiant apporté par l'additif d'onctuosité contenant une telle combinaison est bien supérieur à celui prévisible par ajout des pouvoirs lubrifiants de chacun de ses composants pris séparément. Ce résultat imprévisible traduit l'effet de synergie des différents composants de la dite combinaison au regard de la lubrification. We realized that the lubricating power provided by the oiliness additive containing such a combination is much higher than foreseeable by adding powers lubricants of each of its components taken separately. This unpredictable result reflects the synergistic effect of different components of the said combination with regard to the lubrication.
Dans un premier mode de réalisation, le compose hydrocarboné polycyclique est choisi dans le groupe constitué par les acides résiniques naturels obtenus à partir des résidus de distillation des huiles naturelles extraites des arbres résineux, notamment des conifères résineux, ainsi que les carboxylates d'amines, les esters et les nitriles de ces acides.In a first mode of realization, the polycyclic hydrocarbon compound is chosen from the group consisting of the natural resin acids obtained from the distillation residues of natural oils extracted from coniferous trees, especially conifers resinous, as well as amine carboxylates, esters and the nitriles of these acids.
Parmi les acides résiniques, on préfère l'acide abiétique, l'acide dihydroabiétique, l'acide tétrahydroabiétique, l'acide dehydroabiétique, l'acide néoabiétique, l'acide pimarique, l'acide levopimarique et l'acide parastrinique et leurs dérivés. Among the resin acids, the acid is preferred. abietic, dihydroabietic acid, acid tetrahydroabietic, dehydroabietic acid, acid neoabietic, pimaric acid, levopimaric acid and parastrinic acid and their derivatives.
Selon l'invention, l'hydrocarbure aliphatique monocarboxylique est sous forme d'acide, de carboxylate d'amines et d'esters.According to the invention, the aliphatic hydrocarbon monocarboxylic is in the form of acid, carboxylate amines and esters.
Dans un mode plus poussé de l'invention, la combinaison comprend de 1 à 50% en poids d'au moins un composé hydrocarboné polycyclique, et de 50 à 99% en poids d'au moins un acide monocarboxylique linéaire, saturé ou insaturé, comprenant de 12 à 24 atomes de carbones, ces produits étant présents sous forme d'acide, de carboxylate d'amines ou d'esters.In a more advanced mode of the invention, the combination comprises from 1 to 50% by weight of at least one polycyclic hydrocarbon compound, and from 50 to 99% by weight of at least one acid linear monocarboxylic, saturated or unsaturated, comprising 12 to 24 carbon atoms, these products being present under form of acid, carboxylate of amines or esters.
Par carboxylates d'amines, on entend les composés résultant de la réaction de ces acides avec des amines ou polyamines primaires, secondaires et tertiaires comprenant de 1 à 8 atomes de carbone par chaíne et les alkylèneamines et alkylènepolyamines primaires, secondaires ou tertiaires comprenant de 2 à 8 atomes de carbone. Dans un mode préféré de l'invention, ces sels d'amines dérivent d'amines choisies dans le groupe constitué par l'éthyl-2-hexylamine, la N,N-dibutylamine, l'éthylènediamine, la diéthylènetriamine et la tétraéthylènepentamine.By amine carboxylates is meant the compounds resulting from the reaction of these acids with amines or primary, secondary and tertiary polyamines including from 1 to 8 carbon atoms per chain and the alkylene amines and primary, secondary or tertiary alkylene polyamines comprising from 2 to 8 carbon atoms. In a preferred mode of the invention, these amine salts are derived from selected amines in the group consisting of ethyl-2-hexylamine, N, N-dibutylamine, ethylenediamine, diethylenetriamine and tetraethylenepentamine.
Parmi les esters, on préfère les esters d'alcanols primaires comprenant de 1 à 8 atomes de carbone ou encore des polyalcool du groupe constitué par l'éthylèneglycol, le propylèneglycol, le glycérol, le triméthylolpropane, le pentaérythritol, la diéthanolamine, la triéthanolamine et leurs dérivés.Among the esters, alkanol esters are preferred primary with 1 to 8 carbon atoms or polyalcohols from the group consisting of ethylene glycol, propylene glycol, glycerol, trimethylolpropane, pentaerythritol, diethanolamine, triethanolamine and their derivatives.
Dans un mode préféré de l'invention, le carburant contient de 50 à 1000 ppm de l'additif d'onctuosité.In a preferred embodiment of the invention, the fuel contains 50 to 1000 ppm of the oiliness additive.
Selon la présente invention, on peut ajouter au dit carburant au moins un additif du groupe des additifs usuellement ajoutés dans de tels carburants tels que les additifs détergents, les additifs améliorant l'indice de cétane, les additifs désémulsifiants, les additifs anti-corrosion, les additifs améliorant la tenue à froid, et les additifs modificateurs d'odeur.According to the present invention, one can add to the said fuel at least one additive from the group of additives usually added in such fuels such as detergent additives, additives improving the index of cetane, demulsifying additives, anti-corrosion additives, additives improving cold resistance, and odor modifying additives.
Pour expliciter les avantages de la présente invention au regard de l'art antérieur, des exemples sont donnés ci-après à titre illustratif mais non limitatif de la portée de l'invention revendiquée.To explain the advantages of this invention with regard to the prior art, examples are given below by way of illustration but not limiting of the scope of the claimed invention.
Le présent exemple décrit le choix des additifs en fonction de leur solubilité dans un gazole faiblement soufré.This example describes the choice of additives in function of their solubility in a weak diesel sulfur.
On dilue chaque additif en test à 5% poids dans un gazole (GO) à 500 ppm de soufre, à température ambiante.Each additive in test is diluted to 5% by weight in a diesel (GO) at 500 ppm sulfur, at room temperature.
On désigne par Y les additifs selon l'invention et
par C les exemples comparatifs dans le tableau I ci-après.
Les additifs Y consistent pour une part, en un mélange
d'une combinaison d'acides gras renfermant en poids 50 à 55
% d'acide oléique, 30 à 40 % d'acide linoléique, 3 à 5 %
d'acide palmitique et 1 à 2 % d'acide linolénique, et pour
une autre part en acides résiniques obtenus par distillation
du tall oil, sous produit de fabrication de la pulpe de bois
par le procédé sulfate. Pour les exemples comparatifs, C1
correspond à l'acide oléique pur, C2 au colophane qui est un
mélange d'acides résiniques correspondant au résidu de
distillation des gemmes de pins et C3 est un mélange
d'acides dimères obtenus par dimérisation thermique et/ou
catalytique d'acides gras insaturés.
On constate d'après ce tableau qu'à l'exception des acides résiniques (C2), tous ces composés sont très solubles dans le gazole.It can be seen from this table that, with the exception of resin acids (C 2 ), all of these compounds are very soluble in diesel.
Le présent exemple étudie le pouvoir lubrifiant des additifs décrits dans l'exemple I.This example studies the lubricating power of additives described in Example I.
Le pouvoir lubrifiant de ces additifs a été mesuré dans les conditions de l'essai HFRR (High Frequency Reciprocating Rig) tel que décrit dans l'article SAE 932692 par J.W. HADLEY de l'université de Liverpool.The lubricity of these additives has been measured under the conditions of the HFRR test (High Frequency Reciprocating Rig) as described in article SAE 932692 by J.W. HADLEY of the University of Liverpool.
Le test consiste à imposer conjointement à une bille d'acier en contact avec un plateau métallique immobile, une pression correspondant à un poids de 200 g et un déplacement alternatif de 1 mm à une fréquence de 50 Hz. La bille en mouvement est lubrifiée par la composition à tester. La température est maintenue à 60°C pendant toute la durée de l'essai, c'est-à-dire 75 mn. Le pouvoir lubrifiant est exprimé par la valeur moyenne des diamètres de l'empreinte d'usure de la bille sur le plateau. Un faible diamètre d'usure (généralement inférieur à 400µm) indique un bon pouvoir lubrifiant ; à l'inverse, un diamètre d'usure important (supérieur à 400µm) traduit un pouvoir d'autant plus insuffisant que la valeur du diamètre d'usure est élevée. The test consists in imposing jointly with a ball of steel in contact with a stationary metal plate, a pressure corresponding to a weight of 200 g and a displacement alternating 1 mm at a frequency of 50 Hz. The ball in movement is lubricated by the composition to be tested. The temperature is maintained at 60 ° C for the duration of the test, i.e. 75 min. The lubricity is expressed as the average value of the footprint diameters wear of the ball on the plate. A small diameter wear (generally less than 400µm) indicates good lubricity; conversely, a wear diameter important (greater than 400µm) translates a power of as much more insufficient than the value of the wear diameter is high.
Le pouvoir lubrifiant des additifs a été mesuré sur
un gazole identique à celui de l'exemple I, chaque
échantillon testé ne contenant que 100 ppm d'additif. Les
résultats sont donnés dans le tableau II ci-après.
Ce tableau montre que les additifs (Y1 et Y2) selon l'invention ont un effet identique sinon meilleur que les acides dimères (C3). De plus, on constate que le mélange d'acides gras avec des acides résiniques a un pouvoir lubrifiant bien meilleur que ceux obtenus avec ces mêmes composés pris séparément, traduisant une synergie de ces composants entre eux.This table shows that the additives (Y 1 and Y 2 ) according to the invention have an identical effect if not better than the dimer acids (C 3 ). In addition, it is found that the mixture of fatty acids with resin acids has a much better lubricating power than those obtained with these same compounds taken separately, translating a synergy of these components between them.
Le présent exemple étudie la compatibilité des additifs décrits dans l'exemple I avec les lubrifiants utilisés usuellement dans les moteurs diesel selon le protocole décrit ci-après.This example studies the compatibility of additives described in Example I with lubricants usually used in diesel engines according to the protocol described below.
70 ml d'une huile moteur de basicité totale égale à 15 mg de KOH par gramme sont mélangés avec 700 ml de gazole à 500 ppm de soufre identique à celui de l'exemple I, dans lequel on rajoute 35 g d'additif. Chaque mélange ainsi constitué est placé dans une étuve à 50°C, puis on évalue visuellement la présence ou l'absence de dépôts, d'un précipité ou d'un trouble résultant d'une incompatibilité entre les additifs dits « d'onctuosité », au pouvoir lubrifiant suffisant, avec un lubrifiant moteur appelé KM2+ commercialisé par la société des Huiles Renault Diesel.70 ml of engine oil with total basicity equal to 15 mg of KOH per gram are mixed with 700 ml of diesel at 500 ppm of sulfur identical to that of Example I, in which is added 35 g of additive. Each mixture as well constituted is placed in an oven at 50 ° C, then evaluated visually the presence or absence of deposits, a precipitate or disorder resulting from incompatibility between so-called "oiliness" additives sufficient lubricant, with an engine lubricant called KM2 + marketed by the company of Huiles Renault Diesel.
Les résultats de compabilité sont rassemblés dans le
tableau III ci-après.
Les additifs de l'invention, Y1 et Y2 ne donnent ni dépôt, ni trouble lorsque que le gazole additivé à 100 ppm est ajouté à l'huile.The additives of the invention, Y 1 and Y 2 give no deposit or cloudiness when the diesel fuel with 100 ppm additive is added to the oil.
Le présent exemple vise à décrire des additifs d'onctuosité adaptés pour être introduits dans les carburants selon l'invention.The purpose of this example is to describe additives oiliness adapted to be introduced into fuels according to the invention.
Ce sont d'une part des esters obtenus en faisant réagir des alcools avec l'additif Y1 de l'exemple I dans un mélange équimolaire, à maintenir ce mélange à reflux entre 130 et 150°C sous pression atmosphérique, puis à distiller l'azéotrope eau/toluène.These are, on the one hand, esters obtained by reacting alcohols with the additive Y 1 of Example I in an equimolar mixture, in maintaining this mixture at reflux between 130 and 150 ° C. under atmospheric pressure, then in distilling l water / toluene azeotrope.
D'autre part, il s'agit de carboxylates d'amine obtenues par simple mélange à température ambiante et à pression atmosphérique de Y1 avec une amine ou polyamine selon l'invention, permettant ainsi la neutralisation des sites carboxyliques. On the other hand, they are amine carboxylates obtained by simple mixing at room temperature and at atmospheric pressure of Y 1 with an amine or polyamine according to the invention, thus allowing the neutralization of the carboxylic sites.
Ces additifs sont introduits dans un gazole tel que décrit dans l'exemple II à une concentration de 100 ppm.These additives are introduced into a diesel such as described in Example II at a concentration of 100 ppm.
Le tableau IV rassemble ci-après les résultats du
test d'usure décrit dans l'exemple II obtenus avec le gazole
ainsi dopé pour caractériser leur pouvoir lubrifiant.
D'après ces résultats, on confirme que les carburants dopés par de tels additifs selon l'invention, ont un bon pouvoir lubrifiant.From these results, it is confirmed that the fuels doped with such additives according to the invention have good lubricity.
Claims (11)
- The use, for improving the lubricating properties of low-sulphur content diesel fuels, of a lubricity additive constituted by a combination of at least one saturated or unsaturated, linear monocarboxylic aliphatic hydrocarbon containing from 12 to 24 carbon atoms, and at least one polycyclic hydrocarbon compound chosen from the group consisting of the natural rosin acids obtained from residues of distillation of natural oils extracted from resinous trees, especially resinous coniferous trees, and the derivatives: amine carboxylates, esters and nitriles of these acids.
- Use according to claim 1, wherein the diesel engine fuel has a sulphur content lower than 500 ppm, and corresponds to at least one middle distillate originating from a direct distillation cut of crude oil, at temperatures of between 150 and 400°C.
- Use according to claim 1 or 2, wherein the additive is used in an amount of at least 20 ppm and more than 60 ppm of additive when the said additive is tall oil.
- Use according to claim 3, wherein the additive is used in an amount of from 50 to 1000 ppm.
- Use according to one of claims 1 to 4, wherein the rosin acids are chosen from the group consisting of abietic acid, dihydroabietic acid, tetrahydroabietic acid, dehydroabietic acid, neoabietic acid, pimaric acid, levopimaric acid, parastrinic acid and their derivatives.
- Use according to one of claims 1 to 5, wherein the monocarboxylic aliphatic hydrocarbon is in the form of acid, of amine carboxylate and/or of esters.
- Use according to one of claims 1 to 6, wherein the additive comprises from 1 to 50 % by weight of at least one polycyclic hydrocarbon compound, and from 50 to 99 % by weight of at least one saturated or unsaturated, linear monocarboxylic aliphatic hydrocarbon containing from 12 to 24 carbon atoms.
- Use according to one of claims 1 to 7, wherein the amine carboxylates result from the reaction of these acids with primary, secondary and tertiary amines or polyamines containing from 1 to 8 carbon atoms per chain and primary, secondary or tertiary alkyleneamines and alkylenepolyamines containing from 2 to 8 carbon atoms.
- Use according to claim 8, wherein the amines from which the amine carboxylates are derived are chosen from the group consisting of 2-ethylhexylamine, N,N-dibutylamine, ethylenediamine, diethylene triamine and tetraethylenepentamine.
- Use according to one of claims 1 to 7, wherein the esters result from the reaction of these acids with alcohols of the group consisting of the primary alcohols containing from 1 to 8 carbon atoms and polyalcohols of the ethylene glycol, propylene glycol, glycerol, trimethylolpropane, pentaerythritol, diethanolamine and triethanolamine type.
- Use according to one of claims 1 to 10, wherein at least one additive from the group of the additives usually added to such fuels is added to the said fuel, such as detergent additives, cetane-improving additives, deemulsifying additives, anticorrosion additives, cold-flow additives and odour-modifying additives.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK03003395.5T DK1310547T3 (en) | 1996-07-31 | 1997-07-29 | Low sulfur fuel for diesel engines |
EP03291021A EP1340801A1 (en) | 1996-07-31 | 1997-07-29 | Oiliness additive |
EP03003395.5A EP1310547B1 (en) | 1996-07-31 | 1997-07-29 | Fuel with low sulphur content for diesel engines |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9609662A FR2751982B1 (en) | 1996-07-31 | 1996-07-31 | ONCTUOSITY ADDITIVE FOR ENGINE FUEL AND FUEL COMPOSITION |
FR9609662 | 1996-07-31 | ||
PCT/FR1997/001417 WO1998004656A1 (en) | 1996-07-31 | 1997-07-29 | Fuel with low sulphur content for diesel engines |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03291021A Division EP1340801A1 (en) | 1996-07-31 | 1997-07-29 | Oiliness additive |
EP03003395.5A Division EP1310547B1 (en) | 1996-07-31 | 1997-07-29 | Fuel with low sulphur content for diesel engines |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0915944A1 EP0915944A1 (en) | 1999-05-19 |
EP0915944B1 true EP0915944B1 (en) | 2003-10-22 |
Family
ID=9494685
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97935651A Revoked EP0915944B1 (en) | 1996-07-31 | 1997-07-29 | Use of an additive for the improvement of lubricating properties of a fuel with low sulphur content for diesel engines |
EP03003395.5A Expired - Lifetime EP1310547B1 (en) | 1996-07-31 | 1997-07-29 | Fuel with low sulphur content for diesel engines |
EP03291021A Ceased EP1340801A1 (en) | 1996-07-31 | 1997-07-29 | Oiliness additive |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03003395.5A Expired - Lifetime EP1310547B1 (en) | 1996-07-31 | 1997-07-29 | Fuel with low sulphur content for diesel engines |
EP03291021A Ceased EP1340801A1 (en) | 1996-07-31 | 1997-07-29 | Oiliness additive |
Country Status (23)
Country | Link |
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US (2) | US6592639B2 (en) |
EP (3) | EP0915944B1 (en) |
JP (1) | JP3129446B2 (en) |
KR (1) | KR100485452B1 (en) |
AR (1) | AR008413A1 (en) |
AT (1) | ATE252628T1 (en) |
AU (1) | AU3855497A (en) |
BR (1) | BR9711613A (en) |
DE (1) | DE69725726T2 (en) |
DK (2) | DK1310547T3 (en) |
ES (2) | ES2610592T3 (en) |
FR (1) | FR2751982B1 (en) |
HU (1) | HU223273B1 (en) |
ID (1) | ID19202A (en) |
MX (1) | MX222887B (en) |
MY (1) | MY121253A (en) |
NO (1) | NO990446D0 (en) |
PL (1) | PL186421B1 (en) |
PT (2) | PT915944E (en) |
RU (1) | RU2165447C2 (en) |
SK (1) | SK285505B6 (en) |
WO (1) | WO1998004656A1 (en) |
ZA (1) | ZA976792B (en) |
Families Citing this family (130)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9807607D0 (en) * | 1998-04-08 | 1998-06-10 | Bp Chem Int Ltd | Fuel additive |
DE19830818A1 (en) | 1998-07-09 | 2000-01-13 | Basf Ag | Fuel compositions containing propoxylate |
EP1116780B1 (en) * | 2000-01-11 | 2005-08-31 | Clariant GmbH | Polyfunctional additive for fuel oils |
DE10058359B4 (en) * | 2000-11-24 | 2005-12-22 | Clariant Gmbh | Fuel oils with improved lubricity, containing mixtures of fatty acids with paraffin dispersants, and a lubricant-improving additive |
DE10058357B4 (en) * | 2000-11-24 | 2005-12-15 | Clariant Gmbh | Fatty acid mixtures of improved cold stability, which contain comb polymers, as well as their use in fuel oils |
DE10058356B4 (en) * | 2000-11-24 | 2005-12-15 | Clariant Gmbh | Fuel oils with improved lubricity, containing reaction products of fatty acids with short-chain oil-soluble amines |
DE10143021A1 (en) * | 2001-09-01 | 2003-03-20 | Cognis Deutschland Gmbh | Lubricity improver for diesel oil |
US6866690B2 (en) * | 2002-04-24 | 2005-03-15 | Ethyl Corporation | Friction modifier additives for fuel compositions and methods of use thereof |
DE10313883A1 (en) * | 2003-03-27 | 2004-10-07 | Basf Ag | Additive mixture to improve the lubricity properties of mineral oil products |
KR100743160B1 (en) * | 2003-09-02 | 2007-07-27 | 엘비엘코프 주식회사 | Fuel dope comprising amino polyoxyalkylene rosin ester compound and substitutive fuel comprising the fuel dope and ethanol |
US7256162B2 (en) * | 2003-09-26 | 2007-08-14 | Arizona Chemical Company | Fatty acid esters and uses thereof |
KR100743161B1 (en) * | 2003-10-31 | 2007-07-27 | 오세철 | Fuel dope comprising N-aminoalkylene polyoxyakylene rosin ester compound and substitutive fuel comprising the fuel dope and ethanol |
FR2888248B1 (en) * | 2005-07-05 | 2010-02-12 | Total France | LUBRICATING COMPOSITION FOR HYDROCARBON MIXTURE AND PRODUCTS OBTAINED |
WO2007022169A1 (en) * | 2005-08-15 | 2007-02-22 | Arizona Chemical Company | Low sulfur tall oil fatty acid |
EP1770151A1 (en) * | 2005-09-30 | 2007-04-04 | Infineum International Limited | Additive concentrate |
WO2007082825A1 (en) | 2006-01-18 | 2007-07-26 | Basf Se | Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates |
US20080141582A1 (en) * | 2006-12-13 | 2008-06-19 | Angela Priscilla Breakspear | Additive Composition |
US7626063B2 (en) * | 2007-05-11 | 2009-12-01 | Conocophillips Company | Propane utilization in direct hydrotreating of oils and/or fats |
GT200700043A (en) * | 2007-05-25 | 2008-03-03 | NITRILE FUNCTION BIO COMPOSITES | |
FR2925909B1 (en) * | 2007-12-26 | 2010-09-17 | Total France | BIFUNCTIONAL ADDITIVES FOR LIQUID HYDROCARBONS OBTAINED BY GRAFTING FROM COPOLYMERS OF ETHYLENE AND / OR PROPYLENE AND VINYL ESTERS |
FR2940314B1 (en) | 2008-12-23 | 2011-11-18 | Total Raffinage Marketing | GASOLINE FUEL FOR DIESEL ENGINE HAVING HIGH CARBON CONTENT OF RENEWABLE ORIGIN AND OXYGEN |
FR2943678B1 (en) | 2009-03-25 | 2011-06-03 | Total Raffinage Marketing | LOW MOLECULAR WEIGHT (METH) ACRYLIC POLYMERS, FREE FROM SULFUR, METAL AND HALOGEN COMPOUNDS AND LOW RESIDUAL MONOMER RATES, PREPARATION METHOD AND USES THEREOF |
FR2947558B1 (en) | 2009-07-03 | 2011-08-19 | Total Raffinage Marketing | TERPOLYMER AND ETHYLENE / VINYL ACETATE / UNSATURATED ESTERS AS ADDITIVES TO ENHANCE COLD LIQUID HYDROCARBONS LIKE MEDIUM DISTILLATES AND FUELS OR COMBUSTIBLES |
US8790426B2 (en) | 2010-04-27 | 2014-07-29 | Basf Se | Quaternized terpolymer |
EP2563822A1 (en) | 2010-04-27 | 2013-03-06 | Basf Se | Quaternized terpolymer |
ES2680571T3 (en) | 2010-06-25 | 2018-09-10 | Basf Se | Quaternized copolymer |
US8911516B2 (en) | 2010-06-25 | 2014-12-16 | Basf Se | Quaternized copolymer |
MX2013000054A (en) | 2010-07-06 | 2013-03-18 | Basf Se | Acid-free quaternised nitrogen compounds and use thereof as additives in fuels and lubricants. |
US20120144731A1 (en) * | 2010-12-14 | 2012-06-14 | Basf Se | Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for increasing the cetane number of fuel oils |
FR2969620B1 (en) | 2010-12-23 | 2013-01-11 | Total Raffinage Marketing | MODIFIED ALKYLPHENOL ALDEHYDE RESINS, THEIR USE AS ADDITIVES IMPROVING THE COLD PROPERTIES OF LIQUID HYDROCARBON FUELS AND FUELS |
FR2971254B1 (en) | 2011-02-08 | 2014-05-30 | Total Raffinage Marketing | LIQUID COMPOSITIONS FOR MARKING LIQUID HYDROCARBON FUELS AND FUELS, FUELS AND FUELS CONTAINING THEM, AND METHOD OF DETECTING MARKERS |
US20130133243A1 (en) | 2011-06-28 | 2013-05-30 | Basf Se | Quaternized nitrogen compounds and use thereof as additives in fuels and lubricants |
EP2540808A1 (en) | 2011-06-28 | 2013-01-02 | Basf Se | Quaternised nitrogen compounds and their use as additives in fuels and lubricants |
EP2589647A1 (en) | 2011-11-04 | 2013-05-08 | Basf Se | Quaternised polyether amines and their use as additives in fuels and lubricants |
US8641788B2 (en) | 2011-12-07 | 2014-02-04 | Igp Energy, Inc. | Fuels and fuel additives comprising butanol and pentanol |
EP2604674A1 (en) | 2011-12-12 | 2013-06-19 | Basf Se | Use of quaternised alkylamine as additive in fuels and lubricants |
JP5850569B2 (en) * | 2011-12-28 | 2016-02-03 | 花王株式会社 | Light oil additive |
ES2711361T3 (en) | 2012-02-10 | 2019-05-03 | Basf Se | Imidazolium salts as additives for fuels and fuels |
US9062266B2 (en) | 2012-02-10 | 2015-06-23 | Basf Se | Imidazolium salts as additives for fuels |
FR2987052B1 (en) | 2012-02-17 | 2014-09-12 | Total Raffinage Marketing | ADDITIVES ENHANCING WEAR AND LACQUERING RESISTANCE OF GASOLINE OR BIOGAZOLE FUEL |
FR2991992B1 (en) | 2012-06-19 | 2015-07-03 | Total Raffinage Marketing | ADDITIVE COMPOSITIONS AND THEIR USE TO ENHANCE THE COLD PROPERTIES OF FUELS AND FUELS |
FR2994695B1 (en) | 2012-08-22 | 2015-10-16 | Total Raffinage Marketing | ADDITIVES ENHANCING WEAR AND LACQUERING RESISTANCE OF GASOLINE OR BIOGAZOLE FUEL |
CA2889031A1 (en) | 2012-10-23 | 2014-05-01 | Basf Se | Quaternized ammonium salts of hydrocarbyl epoxides and use thereof as additives in fuels and lubricants |
FR3000101B1 (en) | 2012-12-21 | 2016-04-01 | Total Raffinage Marketing | GELIFIED COMPOSITION OF FUEL OR HYDROCARBON FUEL AND PROCESS FOR PREPARING SUCH A COMPOSITION |
FR3000102B1 (en) | 2012-12-21 | 2015-04-10 | Total Raffinage Marketing | USE OF A VISCOSIFYING COMPOUND TO IMPROVE STORAGE STABILITY OF LIQUID HYDROCARBON FUEL OR FUEL |
FR3005061B1 (en) | 2013-04-25 | 2016-05-06 | Total Raffinage Marketing | ADDITIVE FOR IMPROVING THE STABILITY OF OXIDATION AND / OR STORAGE OF LIQUID HYDROCARBON FUELS OR FUELS |
CN104212501B (en) * | 2013-06-05 | 2016-08-03 | 中国石油天然气股份有限公司 | A kind of diesel fuel lubricity modifier and preparation method thereof |
EP2811007A1 (en) | 2013-06-07 | 2014-12-10 | Basf Se | Alkylene oxide and hydrocarbyl-substituted polycarboxylic acid quaternised alkylamine as additives in fuels and lubricants and their use |
KR102271403B1 (en) | 2013-06-07 | 2021-06-30 | 바스프 에스이 | Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants |
ES2728113T3 (en) | 2013-09-20 | 2019-10-22 | Basf Se | Use of special derivatives of quaternized nitrogen compounds, as fuel additives |
US11168273B2 (en) | 2014-01-29 | 2021-11-09 | Basf Se | Polycarboxylic acid-based additives for fuels and lubricants |
WO2015114051A1 (en) | 2014-01-29 | 2015-08-06 | Basf Se | Polymers as additives for fuels and lubricants |
FR3017876B1 (en) | 2014-02-24 | 2016-03-11 | Total Marketing Services | COMPOSITION OF ADDITIVES AND PERFORMANCE FUEL COMPRISING SUCH A COMPOSITION |
FR3017875B1 (en) | 2014-02-24 | 2016-03-11 | Total Marketing Services | COMPOSITION OF ADDITIVES AND PERFORMANCE FUEL COMPRISING SUCH A COMPOSITION |
FR3021663B1 (en) | 2014-05-28 | 2016-07-01 | Total Marketing Services | GELIFIED COMPOSITION OF FUEL OR LIQUID HYDROCARBON FUEL AND PROCESS FOR PREPARING SUCH A COMPOSITION |
PL3511396T3 (en) | 2014-05-30 | 2020-11-16 | The Lubrizol Corporation | Low molecular weight imide containing quaternary ammonium salts |
US20170107441A1 (en) | 2014-05-30 | 2017-04-20 | The Lubrizol Corporation | Epoxide quaternized quaternary ammonium salts |
EP3149127A1 (en) | 2014-05-30 | 2017-04-05 | The Lubrizol Corporation | High molecular weight imide containing quaternary ammonium salts |
WO2015184280A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Imidazole containing quaternary ammonium salts |
US20170096611A1 (en) | 2014-05-30 | 2017-04-06 | The Lubrizol Corporation | Branched amine containing quaternary ammonium salts |
US20170096610A1 (en) | 2014-05-30 | 2017-04-06 | The Lubrizol Corporation | High molecular weight amide/ester containing quaternary ammonium salts |
EP3149123A2 (en) | 2014-05-30 | 2017-04-05 | The Lubrizol Corporation | Coupled quaternary ammonium salts |
EP3514220B1 (en) | 2014-05-30 | 2020-05-20 | The Lubrizol Corporation | Low molecular weight amide/ester containing quaternary ammonium salts |
DE212015000271U1 (en) | 2014-11-25 | 2017-09-06 | Basf Se | Corrosion inhibitors for fuels and lubricants |
EP3056527A1 (en) | 2015-02-11 | 2016-08-17 | Total Marketing Services | Block copolymers and use thereof for improving the cold properties of fuels |
EP3056526A1 (en) | 2015-02-11 | 2016-08-17 | Total Marketing Services | Block copolymers and use thereof for improving the cold properties of fuels |
WO2017006141A1 (en) | 2015-07-06 | 2017-01-12 | Rhodia Poliamida E Especialidades Ltda | Diesel compositions with improved cetane number and lubricity performances |
US11085001B2 (en) | 2015-07-16 | 2021-08-10 | Basf Se | Copolymers as additives for fuels and lubricants |
DE212016000150U1 (en) | 2015-07-24 | 2018-03-16 | Basf Se | Corrosion inhibitors for fuels and lubricants |
FR3040709B1 (en) | 2015-09-03 | 2019-06-28 | Total Marketing Services | LUBRICATION ADDITIVE FOR FUEL WITH LOW SULFUR CONTENT. |
EP3144059A1 (en) | 2015-09-16 | 2017-03-22 | Total Marketing Services | Method for preparing microcapsules by double emulsion |
WO2017096175A1 (en) | 2015-12-02 | 2017-06-08 | The Lubrizol Corporation | Ultra-low molecular weight imide containing quaternary ammonium salts having short hydrocarbon tails |
WO2017096159A1 (en) | 2015-12-02 | 2017-06-08 | The Lubrizol Corporation | Ultra-low molecular weight amide/ester containing quaternary ammonium salts having short hydrocarbon tails |
EP3187569B1 (en) | 2015-12-29 | 2019-07-03 | Neste Oyj | Renewable diesel fuel composition |
CN106010690A (en) * | 2016-05-21 | 2016-10-12 | 洪其祥 | Compound fuel additive |
ES2896694T3 (en) | 2016-07-05 | 2022-02-25 | Basf Se | Use of corrosion inhibitors for fuels and lubricants |
WO2018007192A1 (en) | 2016-07-05 | 2018-01-11 | Basf Se | Corrosion inhibitors for fuels and lubricants |
WO2018007486A1 (en) | 2016-07-07 | 2018-01-11 | Basf Se | Polymers as additives for fuels and lubricants |
WO2018007445A1 (en) | 2016-07-07 | 2018-01-11 | Basf Se | Corrosion inhibitors for fuels and lubricants |
CN109312242A (en) | 2016-07-07 | 2019-02-05 | 巴斯夫欧洲公司 | Copolymer as the additive for fuel and lubricant |
FR3054223A1 (en) | 2016-07-21 | 2018-01-26 | Total Marketing Services | COPOLYMER AND ITS USE AS DETERGENT ADDITIVE FOR FUEL |
FR3054225B1 (en) | 2016-07-21 | 2019-12-27 | Total Marketing Services | COPOLYMER FOR USE AS A FUEL DETERGENT ADDITIVE |
FR3054224B1 (en) | 2016-07-21 | 2020-01-31 | Total Marketing Services | COPOLYMER AND ITS USE AS A FUEL DETERGENT ADDITIVE |
FR3054240B1 (en) | 2016-07-21 | 2018-08-17 | Total Marketing Services | USE OF COPOLYMERS FOR IMPROVING THE COLD PROPERTIES OF FUELS OR COMBUSTIBLES |
FR3055135B1 (en) | 2016-08-18 | 2020-01-10 | Total Marketing Services | METHOD FOR MANUFACTURING A LUBRICANT ADDITIVE FOR LOW SULFUR FUEL. |
US11124721B2 (en) | 2016-09-21 | 2021-09-21 | The Lubrizol Corporation | Polyacrylate antifoam components for use in diesel fuels |
US10947467B2 (en) | 2016-12-15 | 2021-03-16 | Basf Se | Polymers as additives for fuels |
EP3555242B1 (en) | 2016-12-19 | 2020-11-25 | Basf Se | Additives for improving the thermal stability of fuels |
WO2018188986A1 (en) | 2017-04-13 | 2018-10-18 | Basf Se | Polymers as additives for fuels and lubricants |
AU2018335769B2 (en) | 2017-09-21 | 2023-11-02 | The Lubrizol Corporation | Polyacrylate antifoam components for use in fuels |
FR3071850B1 (en) | 2017-10-02 | 2020-06-12 | Total Marketing Services | COMPOSITION OF FUEL ADDITIVES |
FR3072095B1 (en) | 2017-10-06 | 2020-10-09 | Total Marketing Services | COMPOSITION OF FUEL ADDITIVES |
FR3073522B1 (en) | 2017-11-10 | 2019-12-13 | Total Marketing Services | NOVEL COPOLYMER AND ITS USE AS A FUEL ADDITIVE |
FR3074498B1 (en) | 2017-12-06 | 2020-09-11 | Total Marketing Services | COMPOSITION OF FUEL ADDITIVES |
FR3074497B1 (en) | 2017-12-06 | 2020-09-11 | Total Marketing Services | COMPOSITION OF FUEL ADDITIVES |
FR3074499B1 (en) | 2017-12-06 | 2020-08-28 | Total Marketing Services | USE OF A SPECIAL COPOLYMER TO PREVENT DEPOSITS ON THE VALVES OF INDIRECT GASOLINE INJECTION ENGINES |
FR3075813B1 (en) | 2017-12-21 | 2021-06-18 | Total Marketing Services | USE OF CROSS-LINKED POLYMERS TO IMPROVE THE COLD PROPERTIES OF FUELS OR FUELS |
WO2019183050A1 (en) | 2018-03-21 | 2019-09-26 | The Lubrizol Corporation | Polyacrylamide antifoam components for use in diesel fuels |
FR3080382B1 (en) | 2018-04-23 | 2020-03-27 | Total Marketing Services | FUEL COMPOSITION WITH HIGH POWER AND FUEL ECO EFFECT |
FR3081879B1 (en) | 2018-05-29 | 2020-11-13 | Total Marketing Services | COMPOSITION OF FUEL AND METHOD OF OPERATION OF AN INTERNAL COMBUSTION ENGINE |
FR3083799B1 (en) | 2018-07-16 | 2021-03-05 | Total Marketing Services | FUEL ADDITIVES, SUGAR-AMID TYPE |
FR3085384B1 (en) | 2018-08-28 | 2021-05-28 | Total Marketing Services | USE OF SPECIFIC COPOLYMERS TO IMPROVE THE COLD PROPERTIES OF FUELS OR FUELS |
FR3085383B1 (en) | 2018-08-28 | 2020-07-31 | Total Marketing Services | COMPOSITION OF ADDITIVES INCLUDING AT LEAST ONE COPOLYMER, A COLD FLUIDIFYING ADDITIVE AND AN ANTI-SEDIMENTATION ADDITIVE |
FR3087788B1 (en) | 2018-10-24 | 2021-06-25 | Total Marketing Services | FUEL ADDITIVES ASSOCIATION |
WO2020109568A1 (en) | 2018-11-30 | 2020-06-04 | Total Marketing Services | Quaternary fatty amidoamine compound for use as an additive for fuel |
FR3091539B1 (en) | 2019-01-04 | 2021-10-01 | Total Marketing Services | Use of specific copolymers to lower the limit temperature of filterability of fuels or combustibles |
FR3092333B1 (en) | 2019-01-31 | 2021-01-08 | Total Marketing Services | Fuel composition based on paraffinic hydrocarbons |
FR3092334B1 (en) | 2019-01-31 | 2022-06-17 | Total Marketing Services | Use of a fuel composition based on paraffinic hydrocarbons to clean the internal parts of diesel engines |
CN114051527A (en) | 2019-06-26 | 2022-02-15 | 巴斯夫欧洲公司 | Novel gasoline fuel additive package |
EP4038166A1 (en) | 2019-09-30 | 2022-08-10 | Basf Se | Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants |
FR3101882B1 (en) | 2019-10-14 | 2022-03-18 | Total Marketing Services | Use of particular cationic polymers as fuel and fuel additives |
FR3103493B1 (en) | 2019-11-25 | 2021-12-10 | Total Marketing Services | Fuel lubricant additive |
FR3103812B1 (en) | 2019-11-29 | 2023-04-07 | Total Marketing Services | Use of Alkyl Phenol Compounds as Detergency Additives |
FR3103815B1 (en) | 2019-11-29 | 2021-12-17 | Total Marketing Services | Use of diols as detergency additives |
CA3162063A1 (en) | 2019-12-19 | 2021-06-24 | The Lubrizol Corporation | Wax anti-settling additive composition for use in diesel fuels |
FR3110914A1 (en) | 2020-05-29 | 2021-12-03 | Total Marketing Services | Use of a fuel composition to clean the internal parts of gasoline engines |
FR3110913B1 (en) | 2020-05-29 | 2023-12-22 | Total Marketing Services | Composition of engine fuel additives |
PL3940043T3 (en) | 2020-07-14 | 2024-02-19 | Basf Se | Corrosion inhibitors for fuels and lubricants |
KR102560066B1 (en) * | 2020-07-28 | 2023-07-26 | 주식회사 아이비티 | Manufacturing process of fuel additive for combustion promotion of liquid fuel |
FR3113063B1 (en) | 2020-07-31 | 2022-08-12 | Total Marketing Services | Use of copolymers with specific molar mass distribution for lowering the filterability limit temperature of fuels or fuels |
US20240101919A1 (en) | 2021-01-27 | 2024-03-28 | Basf Se | Branched primary alkyl amines as additives for gasoline fuels |
FR3122434A1 (en) | 2021-04-30 | 2022-11-04 | Total Marketing Services | Fuel composition rich in aromatic compounds, paraffins and ethanol, and its use in particular in competition vehicles |
FR3122435B1 (en) | 2021-04-30 | 2023-05-12 | Total Marketing Services | Fuel composition rich in aromatic compounds and oxygenated compounds |
EP4105301A1 (en) | 2021-06-15 | 2022-12-21 | Basf Se | New gasoline additive packages |
WO2022263244A1 (en) | 2021-06-16 | 2022-12-22 | Basf Se | Quaternized betaines as additives in fuels |
FR3119625B1 (en) | 2021-07-02 | 2023-02-17 | Totalenergies Marketing Services | Composition of fuel rich in aromatic compounds, paraffins and ether, and its use in motor vehicles |
FR3125298A1 (en) | 2021-07-19 | 2023-01-20 | Totalenergies Marketing Services | Use of an additive composition to reduce emissions from diesel vehicles |
FR3135463A1 (en) | 2022-05-12 | 2023-11-17 | Totalenergies Onetech | Fuel composition with low impact on CO2 emissions, and its use in particular in new vehicles |
FR3137103A1 (en) | 2022-06-23 | 2023-12-29 | Totalenergies Onetech | Fuel composition with low impact on CO2 emissions, and its use in particular in new vehicles |
US20240093111A1 (en) * | 2022-09-16 | 2024-03-21 | Kraton Chemical, Llc | Fuel composition with lubricity modifier |
Family Cites Families (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2363778A (en) * | 1942-12-01 | 1944-11-28 | Du Pont | Stabilization of organic substances |
US2682336A (en) * | 1950-01-04 | 1954-06-29 | Phillips Petroleum Co | Rubber swelling additives for fuels |
US2686713A (en) * | 1950-12-09 | 1954-08-17 | Socony Vacuum Oil Co Inc | Sulfate process tall oil as a rust inhibitor for fuel fractions of mineral oil |
US2692821A (en) * | 1951-06-01 | 1954-10-26 | Gulf Research Development Co | Stable fuel oil compositions |
US2658823A (en) * | 1951-08-28 | 1953-11-10 | Socony Vacuum Oil Co Inc | Fuel oil composition |
US2907646A (en) * | 1955-09-29 | 1959-10-06 | American Oil Co | Rust inhibitor for fuel fractions of mineral oil |
US2854324A (en) * | 1955-11-09 | 1958-09-30 | Petrolite Corp | Fuel oil composition |
US2882232A (en) * | 1955-11-14 | 1959-04-14 | Pure Oil Co | Improving the odor of specialty naphthas |
US2995428A (en) * | 1957-10-21 | 1961-08-08 | Petrolite Corp | Thermally stable distillate fuels |
US3157629A (en) * | 1959-02-13 | 1964-11-17 | West Virginia Pulp & Paper Co | Treatment of tall oil fatty acids |
DE1408371A1 (en) * | 1959-02-13 | 1968-12-05 | Albertuswerke Gmbh | Process for the production of binders for molds and cores |
GB1061161A (en) * | 1963-05-29 | 1967-03-08 | Basic Inc | Fuel oil additives |
US3273981A (en) * | 1963-07-16 | 1966-09-20 | Exxon Research Engineering Co | Anti-wear oil additives |
FR1405551A (en) * | 1963-07-16 | 1965-07-09 | Exxon Research Engineering Co | Anti-wear additives intended to improve the lubricity of liquid hydrocarbons |
US3336123A (en) * | 1964-06-24 | 1967-08-15 | Du Pont | Gasoline anti-stalling composition |
US3468639A (en) * | 1965-08-06 | 1969-09-23 | Chevron Res | Gasolines containing deposit-reducing monoamides of polyamines characterized by improved water tolerance |
US3287273A (en) * | 1965-09-09 | 1966-11-22 | Exxon Research Engineering Co | Lubricity additive-hydrogenated dicarboxylic acid and a glycol |
US3549533A (en) * | 1968-11-22 | 1970-12-22 | Atlantic Richfield Co | Single phase emulsion inhibitor |
GB1264058A (en) * | 1969-05-23 | 1972-02-16 | Texaco Development Corp | Fuel composition |
US3667152A (en) * | 1969-09-26 | 1972-06-06 | Texaco Inc | Fuel composition |
US3969233A (en) * | 1971-10-12 | 1976-07-13 | Lucas William J | Biodegradable internal combustion engine lubricants and motor fuel compositions |
US4204481A (en) * | 1979-02-02 | 1980-05-27 | Ethyl Corporation | Anti-wear additives in diesel fuels |
US4308200A (en) * | 1980-07-10 | 1981-12-29 | Champion International Corporation | Extraction of coniferous woods with fluid carbon dioxide and other supercritical fluids |
GB2158457A (en) * | 1984-05-09 | 1985-11-13 | Perkings Engines Group Limited | Alcohol fuels |
CA1237282A (en) * | 1985-04-12 | 1988-05-31 | Canadian Patents And Development Limited/Societe Canadienne Des Brevets Et D'exploitation Limitee | Preparation of tall oil fuel blend |
GB8510719D0 (en) * | 1985-04-26 | 1985-06-05 | Exxon Chemical Patents Inc | Fuel compositions |
US4690687A (en) * | 1985-08-16 | 1987-09-01 | The Lubrizol Corporation | Fuel products comprising a lead scavenger |
US4804389A (en) * | 1985-08-16 | 1989-02-14 | The Lubrizol Corporation | Fuel products |
US4857073A (en) | 1987-08-27 | 1989-08-15 | Wynn Oil Company | Diesel fuel additive |
FR2628295B1 (en) * | 1988-03-09 | 1991-05-10 | Soyez Jean Louis | LIQUID FUNGICIDAL COMPOSITIONS BASED ON COPPER TALLATES |
US4870135A (en) | 1988-10-06 | 1989-09-26 | The Goodyear Tire & Rubber Company | Tall oil fatty acid mixture in rubber |
US4919683A (en) * | 1988-12-22 | 1990-04-24 | Texaco Inc. | Stable middle distillate fuel-oil compositions |
US5183475A (en) * | 1989-11-09 | 1993-02-02 | Mobil Oil Corporation | Fuel compositions containing reaction products of aromatic triazoles and fatty acids salt as antiwear additives |
FR2677222B1 (en) * | 1991-06-04 | 1997-06-27 | Derives Resiniques Terpenique | FUNGICIDAL COMPOSITION BASED ON COPPER TALLATE ASSOCIATED WITH TERPENIC DERIVATIVES AND ITS MANUFACTURE. |
JPH0665528A (en) * | 1992-08-19 | 1994-03-08 | Ohtsu Tire & Rubber Co Ltd :The | Wood-coating composition containing essential oil |
GB9301119D0 (en) | 1993-01-21 | 1993-03-10 | Exxon Chemical Patents Inc | Fuel composition |
US5258049A (en) * | 1993-02-17 | 1993-11-02 | Arco Chemical Technology, L.P. | Diesel fuel composition |
US5559358A (en) * | 1993-05-25 | 1996-09-24 | Honeywell Inc. | Opto-electro-mechanical device or filter, process for making, and sensors made therefrom |
IT1270954B (en) * | 1993-07-21 | 1997-05-26 | Euron Spa | DIESEL COMPOSITION |
GB9411614D0 (en) * | 1994-06-09 | 1994-08-03 | Exxon Chemical Patents Inc | Fuel oil compositions |
CA2149685C (en) * | 1994-06-30 | 1999-09-14 | Jacques Monnier | Conversion of depitched tall oil to diesel fuel additive |
US5454842A (en) * | 1994-12-02 | 1995-10-03 | Exxon Research & Engineering Co. | Cetane improver compositions comprising nitrated fatty acid derivatives |
WO1996018706A1 (en) * | 1994-12-13 | 1996-06-20 | Exxon Chemical Patents Inc. | Fuel oil compositions |
GB9514480D0 (en) | 1995-07-14 | 1995-09-13 | Exxon Chemical Patents Inc | Additives and fuel oil compositions |
US5882364A (en) * | 1995-07-14 | 1999-03-16 | Exxon Chemical Patents Inc. | Additives and fuel oil compositions |
US6080212A (en) * | 1996-11-13 | 2000-06-27 | Henkel Corporation | Lubricants for diesel fuel |
-
1996
- 1996-07-31 FR FR9609662A patent/FR2751982B1/en not_active Expired - Lifetime
-
1997
- 1997-07-29 US US09/147,604 patent/US6592639B2/en not_active Expired - Lifetime
- 1997-07-29 WO PCT/FR1997/001417 patent/WO1998004656A1/en not_active Application Discontinuation
- 1997-07-29 AT AT97935651T patent/ATE252628T1/en not_active IP Right Cessation
- 1997-07-29 BR BR9711613-0A patent/BR9711613A/en not_active IP Right Cessation
- 1997-07-29 SK SK127-99A patent/SK285505B6/en not_active IP Right Cessation
- 1997-07-29 DK DK03003395.5T patent/DK1310547T3/en active
- 1997-07-29 PT PT97935651T patent/PT915944E/en unknown
- 1997-07-29 PL PL97331372A patent/PL186421B1/en unknown
- 1997-07-29 ES ES03003395.5T patent/ES2610592T3/en not_active Expired - Lifetime
- 1997-07-29 PT PT3003395T patent/PT1310547T/en unknown
- 1997-07-29 DK DK97935651T patent/DK0915944T3/en active
- 1997-07-29 DE DE69725726T patent/DE69725726T2/en not_active Revoked
- 1997-07-29 AU AU38554/97A patent/AU3855497A/en not_active Abandoned
- 1997-07-29 KR KR10-1999-7000828A patent/KR100485452B1/en not_active IP Right Cessation
- 1997-07-29 ES ES97935651T patent/ES2208940T3/en not_active Expired - Lifetime
- 1997-07-29 EP EP97935651A patent/EP0915944B1/en not_active Revoked
- 1997-07-29 EP EP03003395.5A patent/EP1310547B1/en not_active Expired - Lifetime
- 1997-07-29 JP JP10508571A patent/JP3129446B2/en not_active Expired - Lifetime
- 1997-07-29 HU HU9903425A patent/HU223273B1/en active IP Right Grant
- 1997-07-29 EP EP03291021A patent/EP1340801A1/en not_active Ceased
- 1997-07-29 RU RU99104395/04A patent/RU2165447C2/en active
- 1997-07-30 ZA ZA9706792A patent/ZA976792B/en unknown
- 1997-07-30 MY MYPI97003481A patent/MY121253A/en unknown
- 1997-07-31 ID IDP972675A patent/ID19202A/en unknown
- 1997-07-31 AR ARP970103464A patent/AR008413A1/en not_active Application Discontinuation
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1999
- 1999-01-29 NO NO990446A patent/NO990446D0/en unknown
- 1999-02-18 MX MX9901648A patent/MX222887B/en active IP Right Grant
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2003
- 2003-05-29 US US10/446,851 patent/US7374589B2/en not_active Expired - Fee Related
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