EP1591514A2 - Use of additives to improve the odor of hydrocarbon compositions and hydrocarbon compositions comprising such additives. - Google Patents

Use of additives to improve the odor of hydrocarbon compositions and hydrocarbon compositions comprising such additives. Download PDF

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Publication number
EP1591514A2
EP1591514A2 EP05290917A EP05290917A EP1591514A2 EP 1591514 A2 EP1591514 A2 EP 1591514A2 EP 05290917 A EP05290917 A EP 05290917A EP 05290917 A EP05290917 A EP 05290917A EP 1591514 A2 EP1591514 A2 EP 1591514A2
Authority
EP
European Patent Office
Prior art keywords
additive
hydrocarbon
formula
composition
additives
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.)
Granted
Application number
EP05290917A
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German (de)
French (fr)
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EP1591514B1 (en
EP1591514A3 (en
Inventor
Laurent Germanaud
Franck Eydoux
Clarisse Doucet
Denis Fadel
Cécile Chambon
Christian Trémolière
Jean-Paul Mercier
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TotalEnergies Marketing Services SA
Original Assignee
Total France SA
Total Raffinage Marketing SA
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Publication date
Application filed by Total France SA, Total Raffinage Marketing SA filed Critical Total France SA
Priority to PL05290917T priority Critical patent/PL1591514T3/en
Publication of EP1591514A2 publication Critical patent/EP1591514A2/en
Publication of EP1591514A3 publication Critical patent/EP1591514A3/en
Application granted granted Critical
Publication of EP1591514B1 publication Critical patent/EP1591514B1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • 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
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1857—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols

Definitions

  • the present invention relates to a liquid hydrocarbon composition, intended in particular for use as fuel or fuel in engines and thermal machines. More specifically, the present invention relates to a composition of liquid hydrocarbons, the odor of which is improved thanks to the use of an original additive, the family of tricyclodecanes and / or tricyclodecènes. The present invention also relates to the use of such additive to improve the smell of fuels and / or to fight against bacterial proliferation in these.
  • the hydrocarbon compositions, in particular fuels have a characteristic odor, particularly unpleasant for the user. This is why formulators of this type of product now seeks to mask the unpleasant odor, even even give them a pleasant smell by the use of specific additives called also additives or odor masks.
  • patent application WO 91/18961 describes the use, to mask or reduce the odor of a fuel or fuel of petroleum origin, of at least one carboxylic acid ester and alcohol.
  • This ester has at most 25 carbon atoms carbon, and preferably from 4 to 14 carbon atoms. It is advantageous used with a perfume composition comprising selected compounds among aldehydes, ketones, alcohols, other esters, terpenes, with which he would act synergistically.
  • compositions have also been developed for the purpose of hide not so much the smell of the fuel itself, but the smell of gas of exhausts emitted during the combustion of the latter.
  • US Patent 1,348,512 describes an agent masking the smells of exhaust gases and fumes from combustion of middle distillates, such as, in particular, diesel fuels or lamp oils.
  • This agent incorporated into the distillate, consists of a mixture of vanillin with xylene musk.
  • the agent also includes distillation residues of oxo alcohols and / or an ester, an alcohol, a ketone, an aldehyde having from 10 to 20 carbon atoms or a mixture of such compounds.
  • US Patent 3,151,956 recommends incorporating diesel fuels an odor mask comprising benzyl salicylate, preferably in combination with oxo-synthesis derivatives and / or vanillin, synthetic musks (based on ter-butyl-nitro-benzenes), diethyl phthalate, the ionone, eugenol.
  • application WO 01/74141 recommends, in order to reduce the unpleasant odor of these products, to employ a thiazole of formula R- (S) n -TZ- (S) n -R, TZ representing a thiazole ring, in combination with an odor mask consisting of conventional odor compounds including aromatic esters.
  • thiazoles can not be used in fuels, on the one hand because they have different odors from those of lubricants, and on the other hand because of the fact that these compounds provide significant quantities of fuels. nitrogen and sulfur, which goes against the current environmental constraints that require on the contrary to reduce the nitrogen and sulfur content of fuels.
  • compositions described in the prior art have an effectiveness limited.
  • hydrocarbon fuels and fuels very specific olfactory profiles, which may vary according to the types of cuts used (light or heavy) and according to the origin of these cuts. It proves thus particularly difficult to develop an additive or a composition resorption additives that significantly improve the odor of hydrocarbon cuts usually constituting fuels, whatever their nature and origin.
  • the present invention aims at providing a hydrocarbon composition, useful in particular as fuel or fuel, which has an olfactory profile particularly balanced with respect to the compositions known in the prior art.
  • the present invention relates to a hydrocarbon composition
  • a hydrocarbon composition comprising a major proportion of at least one liquid hydrocarbon fraction, characterized in that it comprises from 1 to 2000 ppm by weight of at least one additive of formula (I) below: wherein the cyclopentane ring is saturated or unsaturated, and R1, R2, R3, which may be identical or different, are chosen from hydrogen and hydrocarbon radicals comprising from 1 to 10 carbon atoms and optionally containing one or more heteroatoms, in particular from 1 to 3 heteroatoms.
  • the hydrocarbon radicals can be linear or branched.
  • heteroatom oxygen atoms, nitrogen and sulfur.
  • the additives of formula (I) above have the advantage of masking very appreciable way the smell of fuels and fuels based of hydrocarbons, and even to impart a relatively pleasant odor to the latter.
  • these additives additionally have the unexpected advantage of strengthening, in the matrices very particulars are the hydrocarbon mixtures, the olfactory intensity of the others additive additives, if added, so that the notes of these come out with more intensity than if they were used in the absence of the additive of formula (I). There is thus a synergistic effect between the additive according to the invention and the deodorant additives traditionally used in fuels.
  • the additive of formula (I) has also been unexpectedly substantially reduce the proliferation of bacteria and fungi which usually tend to develop in compositions hydrocarbons, especially when they are contaminated with water. They are revealed indeed to have an excellent effect both bactericidal and fungicidal, and can be used for these purposes both curative and preventive.
  • the invention can not be limited to any specific isomer, each particular isomer which can be used as an additive according to the invention, alone or in mixture with one or more other isomers. Often, these compounds are present as a mixture of some isomers, one of which is majority, and it may be more advantageous to use such a mixture of isomers than to seek, at the cost of expensive separation steps, to isolate the desired isomer.
  • a preferred isomer (generally available in the form of a mixture with other isomers present in a smaller amount) is the one whose configuration is as follows:
  • R3 is selected from hydrogen and alkylcarboxylate radicals of formula R'-COO with R 'linear or branched C1-C4 alkyl radical.
  • R 1 or R 2 is hydrogen.
  • R3 is hydrogen.
  • R 1 is chosen from the alkylcarboxylate radicals of R'-COO formula with R 'C1-C4 alkyl radical, linear or branched.
  • the concentration of the additive of formula (I) in the composition of hydrocarbons is between 1 and 1000 ppm by weight, preferably between 1 and 200 ppm mass.
  • the additive of formula (I) is advantageously employed in the composition of hydrocarbons according to the invention, in combination with at least one other additive it will bring out the particular notes.
  • the additive of formula (I) can so be used with all the compounds used in known manner to improve the smell of fuels. It is thus possible to prepare fuels with a wide range of olfactory profiles and relatively subtle.
  • the ratio by weight additive (I): other additive reodorant is variable in a wide measurement, from 100: 0 (no other additive) to 1:99, especially between 99: 1 to 1:99, example 90:10 to 10:90.
  • the additive of formula (I) according to the invention can thus be integrated with a perfume composition for fuels and which composition comprises this additive in admixture with other additive additives.
  • At least one petrol cut, a distillate cut or a cut essentially paraffinic such as kerdane or a mixture of such cuts is preferable to use.
  • biofuel is meant light alcohols such as methanol, ethanol and corresponding ethers, oils of vegetable and / or animal origin and esters of such oils.
  • the hydrocarbon composition according to the invention can thus be advantageously contain from 0.1 to 60% by weight, and preferably from 0.5 to 50% mass of biofuel.
  • Preferred biofuels are esters of alcohols containing 1 to 4 carbon atoms and fatty acids or mixtures of acids fat containing from 16 to 22 carbon atoms.
  • Biofuels particularly preferred are the methyl esters of vegetable oils such as for example, but without limitation, soybean, rapeseed, sunflower, olive and palm oils.
  • the hydrocarbon composition according to the invention comprises at least one distillate cut.
  • the composition of hydrocarbons according to the invention is a diesel fuel, that is to say a hydrocarbon composition meeting the requirements of the NF EN 590 standard.
  • its fraction distilled according to EN ISO 3405 is less than 65% volume at 250 ° C and greater than 95% volume at 370 ° C
  • its sulfur content according to EN 590 is less than or equal to 350 ppm mass, preferably less than or equal to 50 ppm mass, even more preferably less than or equal to 10 ppm mass.
  • Its content polycyclic aromatic hydrocarbons, determined according to the IP 391 standard is preferably less than or equal to 11% by weight.
  • the hydrocarbon composition according to the invention is a domestic fuel oil, for example as defined in the CSR 441 specifications (dated July 1, 2002) of Union Chamber refining Oil (Paris).
  • its fraction distilled according to standard NF EN ISO 3405 is less than 65% volume at 250 ° C and greater than 85% volume at 350 ° C
  • its content in sulfur according to standard NF EN ISO 14596 is less than or equal to 2000 ppm mass, preferably less than or equal to 1000 ppm mass.
  • the hydrocarbon composition according to the invention can be prepared from very simple way, by incorporating with hydrocarbons (by simple mixing physical) the additive according to the invention, alone or in mixture with the other additives.
  • the invention therefore also comprises a process for preparing a composition hydrocarbons having an improved odor, including mixing all or part of the hydrocarbons with at least one additive of formula (I) as described above.
  • the additive of formula (I) When the additive of formula (I) is used in combination with other additives (such as those mentioned above), it is preferable incorporated into the hydrocarbon composition as a composition fragrant.
  • This perfume composition is advantageously in the form a liquid comprising the additive of formula (I) mixed with the other additives deodorants and optionally an organic solvent.
  • Such a perfume composition advantageously contains from 2 to 50% by mass (solvent not included) of additive (s) of formula (I).
  • the composition of hydrocarbons advantageously comprises from 1 to 5000 ppm by weight, preferably from 5 to 1000 ppm mass of perfume composition.
  • the compound of formula (I), alone or in the form of a perfume composition as described above, is initially mixed with all or part of the other additives that must contain the hydrocarbon composition, thus forming an additive composition which is generally called in the profession "additive package”. Then, in a second step, this additive composition is incorporated by simple mixing in the hydrocarbon composition.
  • This solution has the advantage of being able to formulate ready-to-use additive compositions that can be routed on the different places of preparation of fuels and / or fuels. It is It is also possible to store or even market such compositions additives.
  • Such a composition may also contain other additives, such as inter alia one or more lubricant additives, one or more additives anticorrosion, one or more anti-foam additives. It can be diluted in a suitable organic solvent.
  • the diesel fuel preferably contains from 250 to 5000 ppm volume of a such additive composition.
  • Such a composition may also contain one or more other additives, for example biocidal additives. It can be diluted in a solvent appropriate organic.
  • Domestic fuel oil preferably contains 500 to 5000 ppm volume such an additive composition.
  • the present invention also relates to the use of a compound of formula (I), for improving the odor of hydrocarbon compositions, in particular petrol fuels, diesel fuels and domestic fuel oils.
  • the invention includes a method for improving the odor of hydrocarbon compositions such as, in particular, petrol fuels, diesel fuels and domestic fuel oils, including the addition to all or part of hydrocarbons of at least one additive of formula (I) as described above, alone or mixed with other additives, such as, for example, conventional odor compounds as mentioned above.
  • the present invention finally relates to the use of a compound of formula (I) as a bactericidal agent in hydrocarbon compositions, such as including gasoline fuels, diesel fuels and fuel oil servants. It also relates to the use of a compound of formula (I) as a fungicidal agent in such hydrocarbon compositions.
  • the invention includes a method for eliminating bacteria and / or fungi in hydrocarbon compositions or prevent their appearance in such compositions, this method comprising adding to all or part of the hydrocarbons of at least one compound of formula (I) as described above.
  • This example illustrates the effect of an additive A according to the invention on the odor of a conventional hydrocarbon composition.
  • Additive A used is 3a, 4,5,6,7,7a-hexahydro-4,7-methanoinden-6-yl acetate (also called verdyl acetate). This compound is generally in admixture with its isomer, 3a, 4,5,6,7,7a-hexahydro-4,7-methanoinden-5-yl acetate.
  • N be the number of times or the sample is preferred.
  • p 1/2 the number of critical responses Nc corresponding to the chosen confidence level. If N> Nc, the solution is indeed preferred to the chosen confidence level. Otherwise the gap to the expectation can be put on the effect of chance and it can not be said that the solution is preferred.
  • Nc 44 for a confidence level of 0.1%.
  • This example illustrates the effect on the odor of a hydrocarbon composition conventional, an additive A according to the invention integrated in a perfume composition.
  • the additive A used is identical to that of example 1.
  • the composition of perfume consists of a perfume base B of the type used typically in fuels.
  • This base B includes the following compounds (which are standard components of gas oils, known to those skilled in the art): isoamyl acetate, vanillin, anthranylate methyl, ethyl butyrate, raspberry ketone, C14 aldehyde.
  • the total contents of the additive additives of the two compositions 1 and 2 are therefore identical (70 ppm).
  • the incorporation of the additive A according to the invention therefore significantly improves the efficiency of the conventional deodorant additives. This underlines the importance of the use of additive A within a scented composition for fuels or fuel-based hydrocarbons.
  • This example illustrates the bactericidal effect of an additive A according to the invention on a conventional hydrocarbon composition.
  • the additive A used is identical to that of example 1.
  • the strain of bacteria used is Pseudomonas aeruginosa (ATCC33988). The day before inoculation, this The bacterium is cultured in a liquid medium, with an incubation time of 16 hours at 37 ° C.
  • Two hydrocarbon compositions are prepared as follows: two samples of 300 g of cut C are taken and placed in flasks of 1000 ml in brown glass. Additive A is added with the following concentrations: 0 (control, according to the prior art), 107 ppm (according to the invention). The bottles are closed in a non-hermetic manner. The contents of each bottle are stirred using a magnetic bar at room temperature.
  • the inoculation of the two samples is carried out at t o in the following manner: the initial culture (concentration of which is 10 9 cfu / ml) is diluted 1/10 in physiological saline.
  • the physiological saline used is prepared by dissolving 8 g of NaCl in 1000 ml of distilled water). 15 ml of the suspension thus diluted in the two hydrocarbon samples are added.
  • cfu means "colony forming unit": 1 cfu corresponds to 1 cultivable cell.
  • a sample is taken in each vial: 0.2 ml of aqueous phase is taken from each vial (after stopping the stirring and decantation), which is replaced by the same volume of physiological saline.
  • 50 .mu.l are added to a tube containing 5 ml of Tryptone-salt (10 -2 dilution).
  • the Tryptone-salt solution used in Examples 3 and 4 is prepared by dissolving 1 g of tryptone and 8.5 g of NaCl in 1000 ml of distilled water.
  • cascade dilutions up to 10 -4 (10 -6 for the control) are carried out with physiological saline.
  • PCA agar medium For counting the bacteria, 100 ⁇ l of each dilution PCA agar medium ("flat count agar").
  • PCA agar is prepared by mixing 2.5 g of yeast extract, 5 g of tryptone, 1 g of glucose, 15 g of agar and 1000 ml distilled water.
  • the initial concentration at t o in each vial is 2.9 ⁇ 10 8 cfu / ml.
  • the concentration of bacteria after 24 hours is 10 3 cfu / ml.
  • the concentration of bacteria after 24 hours is less than 10 cfu / ml, that is to say almost zero.
  • This example illustrates the fungicidal effect of an additive A according to the invention on a conventional hydrocarbon composition.
  • the additive A used is identical to that of Example 1.
  • the mold strain used is Hormoconis resinae (ATCC20495). The day before inoculation, this mold is grown on a petri dish, with a 24 hour incubation time at 30 ° C.
  • the inoculation of the two samples is carried out at t o in the following manner: 5 ml of physiological saline are introduced into the Petri dish containing the colonies, and lightly rubbed in order to detach the spores. An enumeration is then carried out under a microscope using a Malassez cell. The concentration is 2.2.10 7 spores / ml. After appropriate dilution of this suspension in the two hydrocarbon samples, the concentration obtained in each vial at t o is 5.10 3 cfu / ml.
  • Samples are taken from each of the two vials at regular time intervals (at t o , t o + 24 h, t o + 48 h, t o + 72 h, t o + 7 days).
  • 0.2 ml of aqueous phase is taken from each vial (after stopping the stirring and decantation) which is replaced by the same volume of physiological saline.
  • 50 .mu.l are added to a tube containing 5 ml of Tryptone-salt (10 -2 dilution). After homogenization, cascade dilutions up to 10 -4 (10 -6 for the control) are carried out with physiological saline.
  • the boxes are left overnight cover up to impregnate well the medium and then incubated for 3 days at 30 ° C.
  • the count of molds is done according to ASTM E1259-94.

Abstract

Hydrocarbon composition (A) comprising a major portion of at least a hydrocarbon liquid fraction (fuels or combustibles) comprises at least an additive (I) (1-2000 ppm mass). Hydrocarbon composition (A) comprising a major portion of at least a hydrocarbon liquid fraction (fuels or combustibles) comprises at least an additive (I) (1-2000 ppm mass) (bicyclic compound of formula (Ia)). R 1-R 3H, 1-10C hydrocarbon (optionally comprising one or more heteroatoms). Independent claims are also included for: (1) preparation of (A) having an improved odor; (2) additive composition for diesel oil/domestic fuel oil comprising (% mass): detergent additive (5-50), procetane additive (0-60), filterability additive (0-20), (I) (0.1-20) or perfumed composition (containing the additive); (3) additive composition for domestic fuel oil comprising (% mass): combustion promoter agent (5-60), additive antioxidant (1-20), flow point additive (5-20), (I) (0.1-20) or perfumed composition containing the additive; (4) method to improve the odor of (A) (gasoline fuel, diesel fuel oil or domestic fuel oil) comprising the addition of whole or part of hydrocarbons having (I) (alone or in mixture with other reodorants additives); and (5) method to eliminate bacteria and/or fungi from (A) or to warn their appearance in (A) comprising the addition of whole or part of hydrocarbons having (I). [Image].

Description

La présente invention concerne une composition d'hydrocarbures liquides, destinée en particulier à être utilisée comme carburant ou combustible dans les moteurs et les machines thermiques. Plus précisément, la présente invention concerne une composition d'hydrocarbures liquides, dont l'odeur est améliorée grâce à l'emploi d'un additif original, de la famille des tricyclodecanes et/ou tricyclodecènes. La présente invention concerne également l'utilisation d'un tel additif pour améliorer l'odeur des carburants et combustibles et/ou pour lutter contre la prolifération bactérienne dans ces derniers.The present invention relates to a liquid hydrocarbon composition, intended in particular for use as fuel or fuel in engines and thermal machines. More specifically, the present invention relates to a composition of liquid hydrocarbons, the odor of which is improved thanks to the use of an original additive, the family of tricyclodecanes and / or tricyclodecènes. The present invention also relates to the use of such additive to improve the smell of fuels and / or to fight against bacterial proliferation in these.

De manière connue en soi, les compositions d'hydrocarbures, en particulier les carburants et combustibles, présentent une odeur caractéristique, particulièrement peu agréable pour l'utilisateur. C'est pourquoi les formulateurs de ce type de produits cherchent désormais à en masquer l'odeur désagréable, voire même leur conférer une odeur agréable par l'emploi d'additifs spécifiques appelés aussi additifs réodorants ou masques d'odeurs.In a manner known per se, the hydrocarbon compositions, in particular fuels have a characteristic odor, particularly unpleasant for the user. This is why formulators of this type of product now seeks to mask the unpleasant odor, even even give them a pleasant smell by the use of specific additives called also additives or odor masks.

Ainsi, la demande de brevet WO 91/18961 décrit l'utilisation, pour masquer ou réduire l'odeur d'un carburant ou combustible d'origine pétrolière, d'au moins un ester d'acide carboxylique et d'alcool. Cet ester comporte au plus 25 atomes de carbone, et de préférence de 4 à 14 atomes de carbone. Il est avantageusement employé avec une composition parfumante comprenant des composés choisis parmi des aldéhydes, des cétones, des alcools, d'autres esters, des terpènes, avec lesquels il agirait de manière synergique.Thus, patent application WO 91/18961 describes the use, to mask or reduce the odor of a fuel or fuel of petroleum origin, of at least one carboxylic acid ester and alcohol. This ester has at most 25 carbon atoms carbon, and preferably from 4 to 14 carbon atoms. It is advantageous used with a perfume composition comprising selected compounds among aldehydes, ketones, alcohols, other esters, terpenes, with which he would act synergistically.

Certaines compositions ont également été mises au point dans le but de masquer non tant l'odeur du carburant lui-même, mais les odeurs des gaz d'échappements émis lors de la combustion de celui-ci. Ainsi, le brevet US 1.348.512 décrit un agent masquant les odeurs des gaz d'échappements et des fumées de combustion des distillats moyens tels que notamment des carburants diesel ou des pétroles lampants. Cet agent, incorporé au distillat, est constitué d'un mélange de vanilline avec du musc xylène. De préférence, l'agent comprend également des résidus de distillation d'alcools oxo et/ou un ester, un alcool, une cétone, un aldéhyde ayant de 10 à 20 atomes de carbone ou un mélange de tels composés. Some compositions have also been developed for the purpose of hide not so much the smell of the fuel itself, but the smell of gas of exhausts emitted during the combustion of the latter. Thus, US Patent 1,348,512 describes an agent masking the smells of exhaust gases and fumes from combustion of middle distillates, such as, in particular, diesel fuels or lamp oils. This agent, incorporated into the distillate, consists of a mixture of vanillin with xylene musk. Preferably, the agent also includes distillation residues of oxo alcohols and / or an ester, an alcohol, a ketone, an aldehyde having from 10 to 20 carbon atoms or a mixture of such compounds.

Dans le même but, le brevet US 3.151.956 préconise d'incorporer aux carburants diesels un masque d'odeurs comprenant du salicylate de benzyle, de préférence en combinaison avec des dérivés de synthèse oxo et/ou de la vanilline, des muscs de synthèse (à base de ter-butyl-nitro-benzènes), du diéthyl-phtalate, de la ionone, de l'eugénol.For the same purpose, US Patent 3,151,956 recommends incorporating diesel fuels an odor mask comprising benzyl salicylate, preferably in combination with oxo-synthesis derivatives and / or vanillin, synthetic musks (based on ter-butyl-nitro-benzenes), diethyl phthalate, the ionone, eugenol.

Dans un autre domaine, celui des lubrifiants, la demande WO 01/74141 préconise, pour atténuer l'odeur désagréable de ces produits, d'employer un thiazole de formule R-(S)n-TZ-(S)n-R, TZ représentant un noyau thiazole, en combinaison avec un masque d'odeur constitué de composés odorants classiques dont notamment des esters aromatiques. Toutefois de tels thiazoles ne peuvent être employés dans les carburants et combustibles, d'une part parce que ces derniers présentent des odeurs différentes de celles des lubrifiants, et d'autre part en raison du fait que ces composés apportent des quantités non négligeables d'azote et de soufre, ce qui va à l'encontre des contraintes environnementales actuelles qui imposent au contraire de réduire la teneur en azote et soufre des carburants et combustibles.In another field, that of lubricants, application WO 01/74141 recommends, in order to reduce the unpleasant odor of these products, to employ a thiazole of formula R- (S) n -TZ- (S) n -R, TZ representing a thiazole ring, in combination with an odor mask consisting of conventional odor compounds including aromatic esters. However, such thiazoles can not be used in fuels, on the one hand because they have different odors from those of lubricants, and on the other hand because of the fact that these compounds provide significant quantities of fuels. nitrogen and sulfur, which goes against the current environmental constraints that require on the contrary to reduce the nitrogen and sulfur content of fuels.

Les compositions décrites dans l'art antérieur ont toutefois une efficacité limitée. Les carburants et combustibles à base d'hydrocarbures présentent en effet des profils olfactifs très particuliers, et qui peuvent être variables selon les types de coupes employées (légères ou lourdes) et selon l'origine de ces coupes. Il s'avère ainsi particulièrement difficile de mettre au point un additif ou une composition d'additifs réodorants qui permettent d'améliorer de manière notable l'odeur des coupes d'hydrocarbures constituant usuellement les carburants et combustibles, quelles que soient leur nature et leur origine.The compositions described in the prior art, however, have an effectiveness limited. In fact, hydrocarbon fuels and fuels very specific olfactory profiles, which may vary according to the types of cuts used (light or heavy) and according to the origin of these cuts. It proves thus particularly difficult to develop an additive or a composition resorption additives that significantly improve the odor of hydrocarbon cuts usually constituting fuels, whatever their nature and origin.

La présente invention vise à proposer une composition d'hydrocarbures, utilisable notamment comme carburant ou combustible, qui présente un profil olfactif particulièrement équilibré par rapport aux compositions connues dans l'art antérieur.The present invention aims at providing a hydrocarbon composition, useful in particular as fuel or fuel, which has an olfactory profile particularly balanced with respect to the compositions known in the prior art.

En effet la Demanderesse a découvert que, de manière surprenante, en incorporant dans la composition d'hydrocarbures un additif constitué d'une famille particulière de composés organiques tricycliques, l'on pouvait non seulement améliorer son odeur, mais également faire ressortir les notes plus subtiles d'autres additifs réodorants éventuellement employés en combinaison avec cet additif particulier.Indeed the Applicant has discovered that, surprisingly, in incorporating into the hydrocarbon composition an additive consisting of a family particularity of tricyclic organic compounds, it was possible not only to improve smell, but also bring out the more subtle notes of other additives optionally used in combination with this particular additive.

A cet effet, la présente invention concerne une composition d'hydrocarbures comprenant une proportion majeure d'au moins une coupe d'hydrocarbures liquides, caractérisée en ce qu'elle comprend de 1 à 2000 ppm en masse d'au moins un additif de formule (I) ci-après :

Figure 00030001
   dans laquelle le cycle cyclopentane est saturé ou insaturé, et
   R1, R2, R3, identiques ou différents, sont choisis parmi l'hydrogène et les radicaux hydrocarbonés comprenant de 1 à 10 atomes de carbone et comportant éventuellement un ou plusieurs hétéroatomes, notamment de 1 à 3 hétéroatomes.For this purpose, the present invention relates to a hydrocarbon composition comprising a major proportion of at least one liquid hydrocarbon fraction, characterized in that it comprises from 1 to 2000 ppm by weight of at least one additive of formula (I) below:
Figure 00030001
wherein the cyclopentane ring is saturated or unsaturated, and
R1, R2, R3, which may be identical or different, are chosen from hydrogen and hydrocarbon radicals comprising from 1 to 10 carbon atoms and optionally containing one or more heteroatoms, in particular from 1 to 3 heteroatoms.

Les radicaux hydrocarbonés peuvent être linéaires ou ramifiés.The hydrocarbon radicals can be linear or branched.

Par hétéroatome on désigne ici les atomes d'oxygène, d'azote et de soufre.By heteroatom is meant here oxygen atoms, nitrogen and sulfur.

Les additifs de formule (I) ci-avant présentent l'avantage de masquer de manière très appréciable l'odeur des carburants et combustibles à base d'hydrocarbures, et même de conférer une odeur relativement agréable à ces derniers.The additives of formula (I) above have the advantage of masking very appreciable way the smell of fuels and fuels based of hydrocarbons, and even to impart a relatively pleasant odor to the latter.

Employés au sein d'une composition d'additifs réodorants, ces additifs présentent en outre l'avantage inattendu de renforcer, dans les matrices très particulières que sont les mélanges d'hydrocarbures, l'intensité olfactive des autres additifs réodorants éventuellement ajoutés, de telle sorte que les notes de ceux-ci ressortent avec plus d'intensité que si ces derniers étaient employés en l'absence de l'additif de formule (I). L'on observe ainsi un effet de synergie entre l'additif selon l'invention et les additifs réodorants employés traditionnellement dans les carburants.Employed in a composition of additive additives, these additives additionally have the unexpected advantage of strengthening, in the matrices very particulars are the hydrocarbon mixtures, the olfactory intensity of the others additive additives, if added, so that the notes of these come out with more intensity than if they were used in the absence of the additive of formula (I). There is thus a synergistic effect between the additive according to the invention and the deodorant additives traditionally used in fuels.

Enfin, l'additif de formule (I) s'est avéré, de manière également inattendue, diminuer de manière substantielle la prolifération des bactéries et des champignons qui ont généralement tendance à se développer dans les compositions d'hydrocarbures, surtout lorsque celles-ci sont contaminées par de l'eau. Il s'est révélé en effet avoir un excellent effet tant bactéricide que fongicide, et peut être employé à ces fins à titre tant curatif que préventif.Finally, the additive of formula (I) has also been unexpectedly substantially reduce the proliferation of bacteria and fungi which usually tend to develop in compositions hydrocarbons, especially when they are contaminated with water. They are revealed indeed to have an excellent effect both bactericidal and fungicidal, and can be used for these purposes both curative and preventive.

La formule générique (I) ci-avant correspond à plusieurs isomères, dont entre autres les isomères suivants :

Figure 00030002
Figure 00030003
The generic formula (I) above corresponds to several isomers, including among others the following isomers:
Figure 00030002
Figure 00030003

L'invention ne saurait être limitée à aucun isomère spécifique, chaque isomère particulier pouvant être employé comme additif selon l'invention, seul ou en mélange avec un ou plusieurs autres isomères. Souvent, ces composés se présentent sous forme d'un mélange de quelques isomères, dont l'un est généralement majoritaire, et il peut être alors plus avantageux d'employer un tel mélange d'isomères que de chercher, au prix d'étapes de séparation coûteuses, à isoler l'isomère désiré.The invention can not be limited to any specific isomer, each particular isomer which can be used as an additive according to the invention, alone or in mixture with one or more other isomers. Often, these compounds are present as a mixture of some isomers, one of which is majority, and it may be more advantageous to use such a mixture of isomers than to seek, at the cost of expensive separation steps, to isolate the desired isomer.

Un isomère préféré (disponible en général sous forme d'un mélange avec d'autres isomères présents en quantité moindre) est celui dont la configuration est la suivante :

Figure 00040001
A preferred isomer (generally available in the form of a mixture with other isomers present in a smaller amount) is the one whose configuration is as follows:
Figure 00040001

De préférence, l'additif est choisi parmi les composés de formule (I) ci-avant, dans laquelle :

  • R1 et R2, identiques ou différents, sont choisis parmi :
  • l'hydrogène
  • les radicaux alkylcarboxylate de formule R-COO
  • les radicaux alkylcarbonyle de formule R-C=O
  • les radicaux alcoxy de formule R-O
   avec R radical hydrocarboné, saturé ou insaturé, comportant de 1 à 4 atomes de carbone, linéaire ou ramifié.Preferably, the additive is chosen from the compounds of formula (I) above, in which:
  • R1 and R2, identical or different, are chosen from:
  • hydrogen
  • the alkylcarboxylate radicals of formula R-COO
  • alkylcarbonyl radicals of formula RC = O
  • alkoxy radicals of formula RO
with R saturated or unsaturated hydrocarbon-based radical containing from 1 to 4 carbon atoms, linear or branched.

De préférence, R3 est choisi parmi l'hydrogène et les radicaux alkylcarboxylate de formule R'-COO avec R' radical alkyle en C1 à C4, linéaire ou ramifié.Preferably, R3 is selected from hydrogen and alkylcarboxylate radicals of formula R'-COO with R 'linear or branched C1-C4 alkyl radical.

De préférence, R1 ou R2 est l'hydrogène. De préférence, R3 est l'hydrogène. De manière encore plus préférée, R1 est choisi parmi les radicaux alkylcarboxylate de formule R'-COO avec R' radical alkyle en C1 à C4, linéaire ou ramifié.Preferably, R 1 or R 2 is hydrogen. Preferably, R3 is hydrogen. Even more preferably, R 1 is chosen from the alkylcarboxylate radicals of R'-COO formula with R 'C1-C4 alkyl radical, linear or branched.

A titre d'exemples d'additifs de formule (I) particulièrement préférés dans le cadre de la présente invention, citons les composés pour lesquels:

  • R2 = R3 = H et R1 = CH3-COO ;
  • R2=R3= H et R1 = C2H5-COO ;
  • R2 = R3 = H et R1 = CH(CH3)2 -COO.
As examples of additives of formula (I) that are particularly preferred in the context of the present invention, there are the compounds for which:
  • R2 = R3 = H and R1 = CH 3 -COO;
  • R2 = R3 = H and R1 = C 2 H 5 -COO;
  • R2 = R3 = H and R1 = CH (CH 3) 2 -COO.

Les composés de formule (I) ci-avant correspondent à des produits couramment disponibles sur le marché, pour d'autres applications. Un certain nombre de fabricants de produits chimiques commercialisent ces produits, qu'ils préparent de manière connue en soi par synthèse chimique. The compounds of formula (I) above correspond to products commonly available on the market, for other applications. Some number of chemical manufacturers market these products, which they prepare in a manner known per se by chemical synthesis.

De préférence, la concentration de l'additif de formule (I) dans la composition d'hydrocarbures est comprise entre 1 et 1000 ppm masse, de préférence entre 1 et 200 ppm masse.Preferably, the concentration of the additive of formula (I) in the composition of hydrocarbons is between 1 and 1000 ppm by weight, preferably between 1 and 200 ppm mass.

L'additif de formule (I) est avantageusement employé, dans la composition d'hydrocarbures selon l'invention, en combinaison avec au moins un autre additif réodorant, dont il fera ressortir les notes particulières. L'additif de formule (I) peut ainsi être employé avec tous les composés utilisés de manière connue pour améliorer l'odeur des carburants et combustibles. L'on peut ainsi préparer des carburants et combustibles présentant des profils olfactifs très variés et relativement subtils. Le ratio en poids additif (I):autre additif réodorant est variable dans une large mesure, de 100:0 (pas d'autre additif) à 1:99, notamment entre 99:1 à 1:99, par exemple 90:10 à 10:90.The additive of formula (I) is advantageously employed in the composition of hydrocarbons according to the invention, in combination with at least one other additive it will bring out the particular notes. The additive of formula (I) can so be used with all the compounds used in known manner to improve the smell of fuels. It is thus possible to prepare fuels with a wide range of olfactory profiles and relatively subtle. The ratio by weight additive (I): other additive reodorant is variable in a wide measurement, from 100: 0 (no other additive) to 1:99, especially between 99: 1 to 1:99, example 90:10 to 10:90.

Des composés odorants très divers peuvent être employés à cet effet. Ils peuvent par exemple être choisis parmi les familles connues pour leur emploi dans des d'additifs réodorants. Citons à titre d'exemples non limitatifs :

  • les aldéhydes aliphatiques et aromatiques tels que par exemple, mais non limitativement, la vanilline ;
  • les esters aliphatiques et aromatiques tels que par exemple, mais non limitativement, l'acétate de benzyle, le benzoate de benzyle ;
  • les hydroxydes tels que par exemple, mais non limitativement, le linalol, les alcools phényléthyliques ;
  • les cétones telles que par exemple, mais non limitativement, le camphre cristallisé, l'éthylmaltol ;
  • les huiles essentielles telles que par exemple, mais non limitativement, l'huile essentielle de girofle clou, l'huile essentielle d'orange zeste ;
  • et leurs mélanges.
A variety of odorous compounds can be used for this purpose. They can for example be chosen from families known for their use in additives. As non-limiting examples:
  • aliphatic and aromatic aldehydes such as for example, but not limited to, vanillin;
  • aliphatic and aromatic esters such as, for example, but not limited to, benzyl acetate, benzyl benzoate;
  • hydroxides such as, for example, but not limited to, linalool, phenylethyl alcohols;
  • ketones such as, for example, but not limited to, crystallized camphor, ethylmaltol;
  • essential oils such as for example, but not limited to, clove essential oil nail, orange peel essential oil;
  • and their mixtures.

De manière particulièrement avantageuse, l'additif de formule (I) selon l'invention peut ainsi être intégré à une composition de parfum pour carburants et combustibles, laquelle composition comprend cet additif en mélange avec d'autres additifs réodorants.In a particularly advantageous manner, the additive of formula (I) according to the invention can thus be integrated with a perfume composition for fuels and which composition comprises this additive in admixture with other additive additives.

Selon la présente invention, l'on emploie de préférence comme coupe d'hydrocarbures au moins une coupe essence, une coupe distillat ou une coupe essentiellement paraffinique comme par exemple le kerdane ou un mélange de telles coupes.According to the present invention, it is preferable to use at least one petrol cut, a distillate cut or a cut essentially paraffinic such as kerdane or a mixture of such cuts.

De manière classique dans l'industrie pétrolière, on désigne par coupe essence les coupes traditionnellement employées dans les carburants pour moteurs à allumage commandé, et dont l'intervalle de distillation selon la norme ASTM D 86 est généralement compris dans la gamme allant de 0°C à 185°C. Les coupes essentiellement paraffiniques de type kerdane ayant un intervalle de distillation de 180 à 230°CIn a conventional manner in the petroleum industry, the term petrol cuts traditionally used in motor fuels spark ignition, and the distillation range of which according to ASTM D 86 is generally in the range of 0 ° C to 185 ° C. Sections essentially paraffinic kerdane type having a distillation range of 180 to 230 ° C

On désigne par distillat les coupes traditionnellement employées dans les carburants destinés à l'aviation et aux moteurs à allumage par compression (carburants diesel), et dans les combustibles tels que par exemple les FOD (Fuel Oil Domestique, c'est à dire les combustibles destinés aux chaudières domestiques), les fiouls, les mazouts, les huiles de chauffe et les mélanges de telles coupes. Ces coupes comprennent notamment :

  • les distillats moyens tels que par exemple les coupes kérosène (intervalle de distillation selon la norme ASTM D 86 généralement compris dans la gamme allant de 160°C à 240°C) et les coupes gazole (intervalle de distillation selon la norme ASTM D 86 généralement compris dans la gamme allant de 160°C à 400°C) ;
  • les distillats plus lourds tels que les distillats sous vide intermédiaires (intervalle de distillation selon la norme ASTM D 1160 généralement compris dans la gamme allant de 350°C à 450°C), les distillats sous vide lourds (intervalle de distillation selon la norme ASTM D 1160 généralement compris dans la gamme allant de 400°C à 550°C), voire les résidus de distillation ;
  • les biocarburants.
Distillate refers to the cuts traditionally used in fuels for aviation and compression ignition engines (diesel fuels), and fuels such as for example FOD (Fuel Oil Domestique, ie fuels domestic boilers), fuel oils, fuel oils, heating oils and mixtures of such cuts. These cuts include:
  • middle distillates such as, for example, kerosene cuts (distillation range according to ASTM D 86 generally in the range from 160 ° C. to 240 ° C.) and gas oil cuts (distillation interval according to ASTM D 86 generally in the range of 160 ° C to 400 ° C);
  • heavier distillates such as intermediate vacuum distillates (distillation range according to ASTM D 1160 generally in the range of 350 ° C to 450 ° C), heavy vacuum distillates (distillation range according to ASTM D 1160 generally in the range of 400 ° C to 550 ° C), or even distillation residues;
  • biofuels.

Ces coupes peuvent être issues du raffinage pétrolier, de l'agriculture (cas des biocarburants), ou être des hydrocarbures de synthèse.These cuts can come from oil refining, agriculture (case biofuels), or be synthetic hydrocarbons.

Par biocarburant on désigne les alcools légers tels que le méthanol, l'éthanol et les éthers correspondants, les huiles d'origine végétale et/ou animale et les esters de telles huiles. La composition d'hydrocarbures selon l'invention peut ainsi avantageusement contenir de 0,1 à 60% en masse, et de préférence de 0,5 à 50% en masse de biocarburant. Les biocarburants préférés sont les esters d'alcools contenant de 1 à 4 atomes de carbone et d'acides gras ou de mélanges d'acides gras contenant de 16 à 22 atomes de carbones. Les biocarburants particulièrement préférés sont les esters méthyliques d'huiles végétales telles que par exemple, mais non limitativement, les huiles de soja, de colza, de tournesol, d'olive, de palme.By biofuel is meant light alcohols such as methanol, ethanol and corresponding ethers, oils of vegetable and / or animal origin and esters of such oils. The hydrocarbon composition according to the invention can thus be advantageously contain from 0.1 to 60% by weight, and preferably from 0.5 to 50% mass of biofuel. Preferred biofuels are esters of alcohols containing 1 to 4 carbon atoms and fatty acids or mixtures of acids fat containing from 16 to 22 carbon atoms. Biofuels particularly preferred are the methyl esters of vegetable oils such as for example, but without limitation, soybean, rapeseed, sunflower, olive and palm oils.

Par hydrocarbures de synthèse, on désigne les hydrocarbures obtenus par synthèse chimique à partir d'hydrocarbures plus légers. Citons par exemple :

  • les hydrocarbures obtenus par synthèse Fischer-Tropsch à partir de gaz naturel, d'autres hydrocarbures légers ou de biomasse ;
  • les hydrocarbures obtenus par homologation du méthane ou d'autres hydrocarbures légers ;
  • les hydrocarbures obtenus par oligomérisation d'oléfines légères.
Synthetic hydrocarbons are hydrocarbons obtained by chemical synthesis from lighter hydrocarbons. For example:
  • hydrocarbons obtained by Fischer-Tropsch synthesis from natural gas, other light hydrocarbons or biomass;
  • hydrocarbons obtained by homologation of methane or other light hydrocarbons;
  • hydrocarbons obtained by oligomerization of light olefins.

De préférence, la composition d'hydrocarbures selon l'invention comprend au moins une coupe distillat. Preferably, the hydrocarbon composition according to the invention comprises at least one distillate cut.

Selon un premier mode de réalisation préféré, la composition d'hydrocarbures selon l'invention est un carburant diesel, c'est à dire une composition d'hydrocarbures répondant aux exigences de la norme NF EN 590. En particulier, sa fraction distillée selon la norme EN ISO 3405 est inférieure à 65% volume à 250°C et supérieure à 95% volume à 370°C, sa teneur en soufre selon la norme EN 590 est inférieure ou égale à 350 ppm masse, de préférence inférieure ou égale à 50 ppm masse, encore plus préférentiellement inférieure ou égale à 10 ppm masse. Sa teneur hydrocarbures aromatiques polycycliques, déterminée selon la norme IP 391, est de préférence inférieure ou égale à 11 % en masse.According to a first preferred embodiment, the composition of hydrocarbons according to the invention is a diesel fuel, that is to say a hydrocarbon composition meeting the requirements of the NF EN 590 standard. particular, its fraction distilled according to EN ISO 3405 is less than 65% volume at 250 ° C and greater than 95% volume at 370 ° C, its sulfur content according to EN 590 is less than or equal to 350 ppm mass, preferably less than or equal to 50 ppm mass, even more preferably less than or equal to 10 ppm mass. Its content polycyclic aromatic hydrocarbons, determined according to the IP 391 standard is preferably less than or equal to 11% by weight.

Selon un second mode de réalisation également préféré, la composition d'hydrocarbures selon l'invention est un fuel oil domestique, par exemple tel que défini dans les spécifications CSR 441 (en date du 1er juillet 2002) de la Chambre Syndicale du Raffinage du Pétrole (Paris).According to a second preferred embodiment also, the hydrocarbon composition according to the invention is a domestic fuel oil, for example as defined in the CSR 441 specifications (dated July 1, 2002) of Union Chamber refining Oil (Paris).

En particulier, sa fraction distillée selon la norme NF EN ISO 3405 est inférieure à 65% volume à 250°C et supérieure à 85% volume à 350°C, sa teneur en soufre selon la norme NF EN ISO 14596 est inférieure ou égale à 2000 ppm masse, de préférence inférieure ou égale à 1000 ppm masse.In particular, its fraction distilled according to standard NF EN ISO 3405 is less than 65% volume at 250 ° C and greater than 85% volume at 350 ° C, its content in sulfur according to standard NF EN ISO 14596 is less than or equal to 2000 ppm mass, preferably less than or equal to 1000 ppm mass.

Par ailleurs, pour une utilisation comme carburant diesel, la composition d'hydrocarbures selon l'invention contient de préférence un ou plusieurs autres additifs, qui peuvent être tout additif usuellement employé dans ce type de carburants, dont par exemple, mais non limitativement :

  • un ou plusieurs additifs procétane, tels que par exemple les nitrates d'alkyle dans lesquels le radical alkyle, linéaire ou ramifié, saturé ou insaturé (de préférence ramifié et saturé) contient de 3 à 20 et de préférence de 5 à 15 atomes de carbone (en particulier le nitrate de 2-éthyl-hexyle), les peroxydes organiques et en particulier les peroxydes d'aryle dans lesquels le groupe aryle est un groupe benzyle ou un groupe benzyle substitué (par exemple le peroxyde de benzoyle), ou les peroxydes d'alkyle dans lesquels le radical alkyle, linéaire ou ramifié, saturé ou insaturé (de préférence ramifié et saturé) contient de 2 à 20 et de préférence de 2 à 15 atomes de carbone (par exemple le peroxyde de tertio-butyle) ;
  • un ou plusieurs additifs de filtrabilité et/ou d'écoulement tels que par exemple les copolymères éthylène / acétate de vinyle (EVA), éthylène / propionate de vinyle (EVP), éthylène / éthanoate de vinyle (EVE), éthylène / méthacrylate de méthyle (EMMA), éthylène / fumarate d'alkyle;
  • un ou plusieurs additifs anti-mousse, tels que par exemple les polysiloxanes, les polysiloxanes oxyalkylés, les amides d'acides gras ;
  • un ou plusieurs additifs détergents et/ou anti-corrosion, tels que par exemple les amines, les succinimides, les alkénylsuccinimides, les polyalkylamines, les polyalkyles polyamines et les polyétheramines ;
  • un ou plusieurs additifs de lubrifiance ou d'anti-usure, tels que par exemple les acides gras et leurs dérivés ester ou amide, les acides carboxyliques mono- et polycycliques et leurs dérivés ester ou amide ; citons à titre d'exemple les acides gras comportant de 10 à 22 atomes de carbone et leurs dérivés amides, leur dérivés esters (esters de monoalcools, esters de polyols, esters partiels de polyols) par exemple les esters d'acide oléique, d'acide linoléique, le monooléate de glycérol, le caprate d'éthyle ;
  • un ou plusieurs additifs de point de trouble, tels que par exemple les terpolymères oléfine à chaíne longue / ester(méth)acrylique / maléimide, les dérivés d'esters d'acides fumarique ou maléique ;
  • un ou plusieurs additifs anti-sédimentation, tels que par exemple les copolymères acide (méth)acrylique / (méth)acrylate d'alkyle amidifié par une polyamine, les alkénylsuccinimides de polyamine, les dérivés d'acide phtalamique et d'amine grasse à double chaíne ;
  • un ou plusieurs additifs polyfonctionnels d'opérabilité à froid, tels que par exemple les polymères à base d'oléfine et de nitrate d'alkényle ;
  • un ou plusieurs additifs antioxydant par exemple à base de phénols, d'amines et leurs mélanges ;
  • un ou plusieurs additifs de conductivité, un ou plusieurs additifs désémulsifiants (par exemple à base de polyglycols), un ou plusieurs additifs réodorants, un ou plusieurs promoteurs métalliques de combustion.
Furthermore, for use as diesel fuel, the hydrocarbon composition according to the invention preferably contains one or more other additives, which may be any additive usually used in this type of fuels, including for example, but not limited to:
  • one or more procetane additives, such as, for example, alkyl nitrates in which the linear or branched, saturated or unsaturated (preferably branched and saturated) alkyl radical contains from 3 to 20 and preferably from 5 to 15 carbon atoms (in particular 2-ethylhexyl nitrate), organic peroxides and in particular aryl peroxides in which the aryl group is a benzyl group or a substituted benzyl group (for example benzoyl peroxide), or peroxides alkyl radicals in which the linear or branched, saturated or unsaturated (preferably branched and saturated) alkyl radical contains from 2 to 20 and preferably from 2 to 15 carbon atoms (for example tert-butyl peroxide);
  • one or more filterability and / or flow additives such as, for example, ethylene / vinyl acetate copolymers (EVA), ethylene / vinyl propionate (EVP), ethylene / vinyl ethanoate (EVE), ethylene / methyl methacrylate (EMMA), ethylene / alkyl fumarate;
  • one or more anti-foam additives, such as, for example, polysiloxanes, oxyalkylated polysiloxanes, fatty acid amides;
  • one or more detergent and / or anticorrosion additives, such as, for example, amines, succinimides, alkenylsuccinimides, polyalkylamines, polyalkylamines and polyetheramines;
  • one or more lubricity or anti-wear additives, such as, for example, fatty acids and their ester or amide derivatives, mono- and polycyclic carboxylic acids and their ester or amide derivatives; by way of example, mention may be made of fatty acids containing from 10 to 22 carbon atoms and their amide derivatives, their ester derivatives (monoalcohol esters, polyol esters, partial polyol esters), for example oleic acid esters, linoleic acid, glycerol monooleate, ethyl caprate;
  • one or more cloud point additives, such as, for example, olefin long chain / (meth) acrylic / maleimide terpolymers, fumaric or maleic acid ester derivatives;
  • one or more anti-sedimentation additives, such as, for example, polyamine-aminated alkylated (meth) acrylic acid / (meth) acrylate copolymers, polyamine alkenylsuccinimides, phthalamic acid and double fatty amine derivatives; chain;
  • one or more polyfunctional cold-operability additives, such as, for example, olefin and alkenyl nitrate-based polymers;
  • one or more antioxidant additives, for example based on phenols, amines and their mixtures;
  • one or more conductivity additives, one or more demulsifying additives (for example based on polyglycols), one or more additive additives, one or more metal combustion promoters.

Pour une utilisation comme fuel oil domestique, la composition d'hydrocarbures selon l'invention contient de préférence un ou plusieurs additifs, en plus de l'additif de formule (I). Ces additifs sont choisis parmi ceux classiquement employés dans ce type de combustibles, dont par exemple, mais non limitativement :

  • un ou plusieurs additifs de filtrabilité et/ou d'écoulement tels que par exemple les copolymères éthylène / acétate de vinyle (EVA), éthylène / propionate de vinyle (EVP), éthylène / éthanoate de vinyle (EVE), éthylène / méthacrylate de méthyle (EMMA), éthylène / fumarate d'alkyle ;
  • un ou plusieurs additifs de point de trouble, tels que par exemple les terpolymères oléfine à chaíne longue / ester(méth)acrylique / maléimide, les dérivés d'esters d'acides fumarique ou maléique ;
  • un ou plusieurs additifs anti-sédimentation, tels que par exemple les copolymères acide (méth)acrylique / (méth)acrylate d'alkyle amidifié par une polyamine, les alkénylsuccinimides de polyamine, les dérivés d'acide phtalamique et d'amine grasse à double chaíne ;
  • un ou plusieurs agent(s) promoteurs de combustion. Comme exemple de tels agents, citons les additifs constitués par un ou plusieurs catalyseurs métalliques ou alcalino-terreux aptes à favoriser les réactions de post-combustion des suies. Les catalyseurs préférés sont à base de magnésium, calcium, baryum, cérium, cuivre, fer ou leurs mélanges ;
  • un ou plusieurs additifs de lubrifiance ou d'anti-usure, tels que par exemple les acides gras et leurs dérivés ester ou amide, les acides carboxyliques mono- et polycycliques et leurs dérivés ester ou amide ; citons à titre d'exemple les acides gras comportant de 10 à 22 atomes de carbone et leurs dérivés amides, leur dérivés esters (esters de monoalcools, esters de polyols, esters partiels de polyols) par exemple les esters d'acide oléique, d'acide linoléique, le monooléate de glycérol, le caprate d'éthyle ;
  • un ou plusieurs additifs antioxydant, par exemple à base de phénols, d'amines et leurs mélanges ;
  • un ou plusieurs additifs biocides, par exemple à base de thiocyanates, de thiobenzothiazoles et leurs mélanges.
For use as domestic fuel oil, the hydrocarbon composition according to the invention preferably contains one or more additives, in addition to the additive of formula (I). These additives are chosen from those conventionally used in this type of fuels, including, for example, but without limitation:
  • one or more filterability and / or flow additives such as, for example, ethylene / vinyl acetate copolymers (EVA), ethylene / vinyl propionate (EVP), ethylene / vinyl ethanoate (EVE), ethylene / methyl methacrylate (EMMA), ethylene / alkyl fumarate;
  • one or more cloud point additives, such as, for example, olefin long chain / (meth) acrylic / maleimide terpolymers, fumaric or maleic acid ester derivatives;
  • one or more anti-sedimentation additives, such as, for example, polyamine-aminated alkylated (meth) acrylic acid / (meth) acrylate copolymers, polyamine alkenylsuccinimides, phthalamic acid and double fatty amine derivatives; chain;
  • one or more combustion promoter (s). Examples of such agents include additives consisting of one or more metal or alkaline earth catalysts capable of promoting post-combustion reactions soot. The preferred catalysts are based on magnesium, calcium, barium, cerium, copper, iron or their mixtures;
  • one or more lubricity or anti-wear additives, such as, for example, fatty acids and their ester or amide derivatives, mono- and polycyclic carboxylic acids and their ester or amide derivatives; by way of example, mention may be made of fatty acids containing from 10 to 22 carbon atoms and their amide derivatives, their ester derivatives (monoalcohol esters, polyol esters, partial polyol esters), for example oleic acid esters, linoleic acid, glycerol monooleate, ethyl caprate;
  • one or more antioxidant additives, for example based on phenols, amines and their mixtures;
  • one or more biocidal additives, for example based on thiocyanates, thiobenzothiazoles and their mixtures.

La composition d'hydrocarbures selon l'invention peut être préparée de manière très simple, en incorporant aux hydrocarbures (par simple mélange physique) l'additif selon l'invention, seul ou en mélange avec les autres additifs. L'invention comprend donc également un procédé de préparation d'une composition d'hydrocarbures présentant une odeur améliorée, comprenant le mélange de tout ou partie des hydrocarbures avec au moins un additif de formule (I) tel que décrit ci-avant.The hydrocarbon composition according to the invention can be prepared from very simple way, by incorporating with hydrocarbons (by simple mixing physical) the additive according to the invention, alone or in mixture with the other additives. The invention therefore also comprises a process for preparing a composition hydrocarbons having an improved odor, including mixing all or part of the hydrocarbons with at least one additive of formula (I) as described above.

Lorsque l'additif de formule (I) est employé en combinaison avec d'autres additifs réodorants (tels que par exemple ceux cités ci-avant), il est de préférence incorporé à la composition d'hydrocarbures sous forme d'une composition parfumée. Cette composition parfumée se présente avantageusement sous la forme d'un liquide comprenant l'additif de formule (I) en mélange avec les autres additifs réodorants et éventuellement un solvant organique.When the additive of formula (I) is used in combination with other additives (such as those mentioned above), it is preferable incorporated into the hydrocarbon composition as a composition fragrant. This perfume composition is advantageously in the form a liquid comprising the additive of formula (I) mixed with the other additives deodorants and optionally an organic solvent.

Une telle composition parfumée contient avantageusement de 2 à 50% en masse (solvant non inclus) d'additif(s) de formule (I). La composition d'hydrocarbures comprend avantageusement de 1 à 5000 ppm masse, de préférence de 5 à 1000 ppm masse de composition parfumée.Such a perfume composition advantageously contains from 2 to 50% by mass (solvent not included) of additive (s) of formula (I). The composition of hydrocarbons advantageously comprises from 1 to 5000 ppm by weight, preferably from 5 to 1000 ppm mass of perfume composition.

Selon un mode de réalisation particulièrement préféré, le composé de formule (I), seul ou sous forme de composition parfumée telle que décrite ci-avant, est dans un premier temps mélangé à tout ou partie des autres additifs que doit contenir la composition d'hydrocarbures, formant ainsi une composition d'additifs que l'on nomme généralement dans la profession « package d'additifs ». Puis, dans un deuxième temps, cette composition d'additifs est incorporée par simple mélange dans la composition d'hydrocarbures. Cette solution présente l'avantage de pouvoir formuler des compositions d'additifs prêtes à l'emploi, qui peuvent être acheminées sur les différents lieux de préparation de carburants et/ou combustibles. Il est également possible de stocker, voire de commercialiser de telles compositions d'additifs.According to a particularly preferred embodiment, the compound of formula (I), alone or in the form of a perfume composition as described above, is initially mixed with all or part of the other additives that must contain the hydrocarbon composition, thus forming an additive composition which is generally called in the profession "additive package". Then, in a second step, this additive composition is incorporated by simple mixing in the hydrocarbon composition. This solution has the advantage of being able to formulate ready-to-use additive compositions that can be routed on the different places of preparation of fuels and / or fuels. It is It is also possible to store or even market such compositions additives.

L'on peut ainsi préparer des compositions d'additifs appropriées au type de composition d'hydrocarbure à laquelle elles sont destinées.It is thus possible to prepare additive compositions suitable for the type of hydrocarbon composition for which they are intended.

Par exemple, une composition d'additifs pour carburant diesel contient avantageusement :

  • de 5 à 50% masse d'au moins un additif détergent ;
  • de 0 à 60% masse d'au moins un additif procétane ;
  • de 0 à 20% masse d'au moins un additif de filtrabilité ;
  • de 0,1 à 20% masse d'au moins un additif de formule (I) ou de composition parfumée contenant un tel additif.
For example, a diesel fuel additive composition advantageously contains:
  • from 5 to 50% by weight of at least one detergent additive;
  • from 0 to 60% by weight of at least one procetane additive;
  • from 0 to 20% by weight of at least one filterability additive;
  • from 0.1 to 20% by weight of at least one additive of formula (I) or of a perfume composition containing such an additive.

Une telle composition peut également contenir d'autres additifs, tels que entre autres un ou plusieurs additifs de lubrifiance, un ou plusieurs additifs anticorrosion, un ou plusieurs additifs anti-mousse. Elle peut être diluée dans un solvant organique approprié.Such a composition may also contain other additives, such as inter alia one or more lubricant additives, one or more additives anticorrosion, one or more anti-foam additives. It can be diluted in a suitable organic solvent.

Le carburant diesel contient de préférence de 250 à 5000 ppm volume d'une telle composition d'additifs.The diesel fuel preferably contains from 250 to 5000 ppm volume of a such additive composition.

De même, une composition d'additifs pour fuel oil domestique contient avantageusement :

  • de 5 à 60% masse d'au moins un agent promoteur de combustion ;
  • de 1 à 20% masse d'au moins un additif antioxydant ;
  • de 5 à 20% masse d'au moins un additif de point d'écoulement ;
  • de 0,1 à 20% masse d'au moins un additif de formule (I) ou de composition parfumée contenant un tel additif.
Likewise, an additive composition for domestic fuel oil advantageously contains:
  • from 5 to 60% by weight of at least one combustion promoter;
  • from 1 to 20% by weight of at least one antioxidant additive;
  • from 5 to 20% by weight of at least one pour point additive;
  • from 0.1 to 20% by weight of at least one additive of formula (I) or of a perfume composition containing such an additive.

Une telle composition peut également contenir un ou plusieurs autres additifs, par exemple des additifs biocides. Elle peut être diluée dans un solvant organique approprié.Such a composition may also contain one or more other additives, for example biocidal additives. It can be diluted in a solvent appropriate organic.

Le fuel oil domestique contient de préférence de 500 à 5000 ppm volume d'une telle composition d'additifs.Domestic fuel oil preferably contains 500 to 5000 ppm volume such an additive composition.

La présente invention concerne également l'utilisation d'un composé de formule (I), pour améliorer l'odeur des compositions d'hydrocarbures, en particulier des carburants essence, des carburants diesels et des fuels oils domestiques. En d'autres termes, l'invention comprend une méthode pour améliorer l'odeur des compositions d'hydrocarbures telles que notamment les carburants essence, les carburants diesels et les fuel oil domestiques, comprenant l'ajout à tout ou partie des hydrocarbures d'au moins un additif de formule (I) tel que décrit ci-avant, seul ou en mélange avec d'autres additifs réodorants, tels que par exemple des composés odorants classiques tels que cités ci-avant.The present invention also relates to the use of a compound of formula (I), for improving the odor of hydrocarbon compositions, in particular petrol fuels, diesel fuels and domestic fuel oils. In in other words, the invention includes a method for improving the odor of hydrocarbon compositions such as, in particular, petrol fuels, diesel fuels and domestic fuel oils, including the addition to all or part of hydrocarbons of at least one additive of formula (I) as described above, alone or mixed with other additives, such as, for example, conventional odor compounds as mentioned above.

La présente invention concerne enfin l'utilisation d'un composé de formule (I) comme agent bactéricide dans les compositions d'hydrocarbures, telles que notamment les carburants essence, les carburants diesels et les fuel oil domestiques. Elle concerne également l'utilisation d'un composé de formule (I) comme agent fongicide dans de telles compositions d'hydrocarbures.The present invention finally relates to the use of a compound of formula (I) as a bactericidal agent in hydrocarbon compositions, such as including gasoline fuels, diesel fuels and fuel oil servants. It also relates to the use of a compound of formula (I) as a fungicidal agent in such hydrocarbon compositions.

En d'autres termes, l'invention comprend une méthode pour éliminer les bactéries et/ou les champignons dans les compositions d'hydrocarbures ou prévenir leur apparition dans de telles compositions, cette méthode comprenant l'ajout à tout ou partie des hydrocarbures d'au moins un composé de formule (I) tel que décrit ci-avant.In other words, the invention includes a method for eliminating bacteria and / or fungi in hydrocarbon compositions or prevent their appearance in such compositions, this method comprising adding to all or part of the hydrocarbons of at least one compound of formula (I) as described above.

L'invention sera illustrée plus en détail par les exemples ci-après, lesquels ne sauraient en limiter la portée.The invention will be further illustrated by the following examples, which can not limit its scope.

EXEMPLESEXAMPLES

Les tests présentés ci-après ont été réalisés sur une même coupe C d'hydrocarbures, à savoir un distillat moyen du type gazole. Cette coupe, qui correspond à une coupe classique servant de base aux carburants diesels, possède les caractéristiques suivantes :

  • Teneur en soufre (norme NF EN ISO 14596) : 320 ppm masse ;
  • Masse volumique à 15°C (norme NF EN ISO 12185) : 837 kg/m3 ;
  • Point de trouble (norme NF EN 23015) : -7°C ;
  • Température limite de filtrabilité (norme NF EN 116) : -8°C ;
  • Point d'écoulement (norme NF T 60-105) : -15°C ;
  • Indice de cétane mesuré (norme ASTM D 613) : 52.1 ;
  • Intervalle de distillation (norme ASTM D 86) :
    • point initial de distillation : 177.5°C
    • point 5% distillation : 200°C
    • point 10% distillation : 209.5°C
    • point 20% distillation : 225.5°C
    • point 30% distillation : 243.5°C
    • point 40% distillation : 258°C
    • point 50% distillation : 270.5°C
    • point 60% distillation : 283°C
    • point 70% distillation : 296.5°C
    • point 80% distillation : 313°C
    • point 90% distillation : 330.5°C
    • point 95% distillation : 344°C
    • point final de distillation : 351.7°C
    • The tests presented below were carried out on the same C section of hydrocarbons, namely a middle distillate of the diesel type. This cut, which corresponds to a conventional cup used as a base for diesel fuels, has the following characteristics:
  • Sulfur content (standard NF EN ISO 14596): 320 ppm mass;
  • Density at 15 ° C (NF EN ISO 12185): 837 kg / m3;
  • Cloud point (standard NF EN 23015): -7 ° C;
  • Filterability limit temperature (NF EN 116 standard): -8 ° C;
  • Pour point (NF T 60-105 standard): -15 ° C;
  • Cetane number measured (ASTM D 613): 52.1;
  • Distillation interval (ASTM D 86):
    • initial point of distillation: 177.5 ° C
    • point 5% distillation: 200 ° C
    • point 10% distillation: 209.5 ° C
    • point 20% distillation: 225.5 ° C
    • point 30% distillation: 243.5 ° C
    • 40% distillation point: 258 ° C
    • 50% point distillation: 270.5 ° C
    • 60% distillation point: 283 ° C
    • 70% distillation point: 296.5 ° C
    • 80% distillation point: 313 ° C
    • 90% distillation point: 330.5 ° C
    • 95% point distillation: 344 ° C
    • final distillation point: 351.7 ° C

    • Exemple 1Example 1

    Cet exemple illustre l'effet d'un additif A selon l'invention sur l'odeur d'une composition d'hydrocarbures classique.This example illustrates the effect of an additive A according to the invention on the odor of a conventional hydrocarbon composition.

    L'additif A utilisé est l'acétate de 3a,4,5,6,7,7a-hexahydro-4,7-méthanoindèn-6-yle (aussi appelé acétate de verdyle). Ce composé est généralement en mélange avec son isomère, l'acétate de 3a,4,5,6,7,7a-hexahydro-4,7-méthanoindèn-5-yle.

    Figure 00120001
    Additive A used is 3a, 4,5,6,7,7a-hexahydro-4,7-methanoinden-6-yl acetate (also called verdyl acetate). This compound is generally in admixture with its isomer, 3a, 4,5,6,7,7a-hexahydro-4,7-methanoinden-5-yl acetate.
    Figure 00120001

    Ce type de composé est couramment disponible dans le commerce. Pour les présents tests, le produit employé est celui commercialisé par la société Sensient sous le nom « Cycloverdol acetate ».This type of compound is commonly available commercially. For the present tests, the product used is that sold by the company Sensient under the name "Cycloverdol acetate".

    Deux compositions d'hydrocarbures ont été réalisées :

    • composition 1 : coupe C seule (composition classique);
    • composition 2 : coupe C + 70 ppm en masse d'additif A (composition conforme à l'invention).
    Two hydrocarbon compositions were made:
    • composition 1: C section alone (conventional composition);
    • composition 2: C-section + 70 ppm by weight of additive A (composition according to the invention).

    L'odeur de ces deux compositions a été comparée au moyen d'un test de préférence, réalisé de la manière suivante :

  • Un jury de 60 personnes a été retenu. Le test de préférence nécessitant un panel de sujets naïfs, aucune sélection n'a été réalisée pour composer ce jury. Le test a été réalisé dans un local comprenant des cabines répondant à la norme AFNOR V09-105 : 5 cabines individuelles séparées physiquement, située dans un endroit calme et possédant une température agréable et un éclairage doux. Entre chaque mesure, les cabines étaient ventilées pendant cinq minutes afin de s'assurer de l'absence de pollution olfactive.
  • Un échantillon de chacune des deux compositions a été présenté dans une cabine individuelle à chaque membre du jury de manière anonyme, de façon à ce que sa composition ne puisse pas être identifiée. Chaque membre du jury a alors indiqué sur une feuille, de manière indépendante des autres et anonyme, quelle composition a selon lui l'odeur la plus agréable.
    • The odor of these two compositions was compared by means of a preference test, carried out as follows:
  • A jury of 60 people was selected. The preference test requires a panel of naive subjects, no selection was made to compose this jury. The test was performed in a room with booths meeting the AFNOR V09-105 standard: 5 individual cabins separated physically, located in a quiet place and having a pleasant temperature and soft lighting. Between each measurement, the booths were ventilated for five minutes to ensure the absence of olfactory pollution.
  • A sample of each of the two compositions was presented in an individual booth to each member of the jury anonymously, so that its composition could not be identified. Each member of the jury then indicated on a sheet, independently of the others and anonymous, which composition according to him has the most pleasant smell.

    • Les résultats ont été analysés selon les recommandations de l'AFNOR, V 09-012 par comparaison avec la loi de distribution binomiale de paramètre p=1/2.The results were analyzed according to the recommendations of the AFNOR, V 09-012 by comparison with the binomial distribution law of parameter p = 1/2.

    Soit N, le nombre de fois ou l'échantillon est préféré. On lit dans la table de la distribution binomiale unilatérale à p = 1/2 le nombre de réponses critiques Nc correspondant au seuil de confiance choisi. Si N > Nc, la solution est effectivement préférée au seuil de confiance choisi. Sinon l'écart à l'espérance mathématique peut être mis sur l'effet du hasard et on ne peut affirmer que la solution est préférée. Pour un panel de 60 personne, Nc = 44 pour un seuil de confiance de 0,1%.Let N be the number of times or the sample is preferred. We read in the table of the binomial one-sided distribution at p = 1/2 the number of critical responses Nc corresponding to the chosen confidence level. If N> Nc, the solution is indeed preferred to the chosen confidence level. Otherwise the gap to the expectation can be put on the effect of chance and it can not be said that the solution is preferred. For a panel of 60 people, Nc = 44 for a confidence level of 0.1%.

    Le résultat suivant a été obtenu: sur les 60 sujets, 48 préfèrent l'odeur de la composition 2 conforme à l'invention à celle de la composition 1 classique.The following result was obtained: of the 60 subjects, 48 prefer the smell of composition 2 according to the invention to that of the composition 1 conventional.

    L'incorporation de l'additif A selon l'invention améliore donc de manière indiscutable l'odeur de la coupe d'hydrocarbures C.The incorporation of the additive A according to the invention thus improves indisputable smell of the C cut.

    Exemple 2Example 2

    Cet exemple illustre l'effet, sur l'odeur d'une composition d'hydrocarbures classique, d'un additif A selon l'invention intégré à une composition de parfum.This example illustrates the effect on the odor of a hydrocarbon composition conventional, an additive A according to the invention integrated in a perfume composition.

    L'additif A utilisé est identique à celui de l'exemple 1. La composition de parfum est constituée d'une base parfumante B du type de celles employées classiquement dans les carburants et combustibles. Cette base B comprend les composés suivants (qui sont des composants classiques des réodorants pour gazoles, connus de l'homme du métier) : acétate d'iso-amyle, vanilline, anthranylate de méthyle, butyrate d'éthyle, « raspberry ketone », aldéhyde C14.The additive A used is identical to that of example 1. The composition of perfume consists of a perfume base B of the type used typically in fuels. This base B includes the following compounds (which are standard components of gas oils, known to those skilled in the art): isoamyl acetate, vanillin, anthranylate methyl, ethyl butyrate, raspberry ketone, C14 aldehyde.

    Deux compositions d'hydrocarbures ont été réalisées :

    • composition 1 : coupe C + 70 ppm en masse de base B (composition classique);
    • composition 2 : coupe C +35 ppm en masse de base B + 35 ppm en masse d'additif A (composition conforme à l'invention).
    Two hydrocarbon compositions were made:
    • Composition 1: C-cut + 70 ppm by weight of base B (conventional composition);
    • composition 2: C-cut +35 ppm by weight of base B + 35 ppm by weight of additive A (composition according to the invention).

    Les teneurs totales en additifs réodorants des deux compositions 1 et 2 sont donc identiques (70 ppm).The total contents of the additive additives of the two compositions 1 and 2 are therefore identical (70 ppm).

    L'odeur de ces deux compositions a été comparée au moyen d'un test de préférence, réalisé de manière strictement identique à celui de l'exemple 1.The odor of these two compositions was compared by means of a test of preferably, carried out in exactly the same way as in Example 1.

    Le résultat suivant a été obtenu: sur les 60 sujets, 54 préfèrent l'odeur de la composition 2 conforme à l'invention à celle de la composition 1 classique.The following result was obtained: of the 60 subjects, 54 prefer the smell of composition 2 according to the invention to that of the composition 1 conventional.

    A teneur en additifs réodorants constante, l'incorporation de l'additif A selon l'invention améliore donc de manière particulièrement sensible l'efficacité des additifs réodorants classiques. Ceci souligne l'intérêt de l'emploi de l'additif A au sein d'une composition parfumée pour carburants ou combustibles à base d'hydrocarbures. With a content of constant additive additives, the incorporation of the additive A according to the invention therefore significantly improves the efficiency of the conventional deodorant additives. This underlines the importance of the use of additive A within a scented composition for fuels or fuel-based hydrocarbons.

    Exemple 3Example 3

    Cet exemple illustre l'effet bactéricide d'un additif A selon l'invention sur une composition d'hydrocarbures classique.This example illustrates the bactericidal effect of an additive A according to the invention on a conventional hydrocarbon composition.

    L'additif A utilisé est identique à celui de l'exemple 1. La souche de bactérie utilisée est Pseudomonas aeruginosa (ATCC33988). La veille de l'inoculation, cette bactérie est cultivée en milieu liquide, avec un temps d'incubation de 16 heures à 37°C.The additive A used is identical to that of example 1. The strain of bacteria used is Pseudomonas aeruginosa (ATCC33988). The day before inoculation, this The bacterium is cultured in a liquid medium, with an incubation time of 16 hours at 37 ° C.

    Deux compositions d'hydrocarbures sont préparées de la manière suivante : on prélève deux échantillons de 300 g de coupe C que l'on place dans des flacons de 1000 ml en verre brun. On ajoute l'additif A avec les concentrations suivantes : 0 (témoin, conforme à l'art antérieur), 107 ppm (selon l'invention). Les flacons sont fermés de façon non hermétique. Les contenus de chaque flacon sont agités à l'aide d'un barreau magnétique, à température ambiante.Two hydrocarbon compositions are prepared as follows: two samples of 300 g of cut C are taken and placed in flasks of 1000 ml in brown glass. Additive A is added with the following concentrations: 0 (control, according to the prior art), 107 ppm (according to the invention). The bottles are closed in a non-hermetic manner. The contents of each bottle are stirred using a magnetic bar at room temperature.

    L'inoculation des deux échantillons est réalisée à to de la manière suivante : la culture initiale (dont la concentration est de 109 cfu/ml) est diluée au 1/10 dans du sérum physiologique. Dans les exemples 3 et 4, le sérum physiologique employé est préparé par dissolution de 8 g de NaCl dans 1000 ml d'eau distillée). On ajoute 15 ml de la suspension ainsi diluée dans les deux échantillons d'hydrocarbures.The inoculation of the two samples is carried out at t o in the following manner: the initial culture (concentration of which is 10 9 cfu / ml) is diluted 1/10 in physiological saline. In Examples 3 and 4, the physiological saline used is prepared by dissolving 8 g of NaCl in 1000 ml of distilled water). 15 ml of the suspension thus diluted in the two hydrocarbon samples are added.

    Dans les présents exemples, le terme cfu signifie « colony forming unit »: 1 cfu correspond à 1 cellule cultivable.In the present examples, the term cfu means "colony forming unit": 1 cfu corresponds to 1 cultivable cell.

    A to et à to + 24 heures, un prélèvement est effectué dans chaque flacon : on prélève 0,2 ml de phase aqueuse dans chaque fiole (après arrêt de l'agitation et décantation), que l'on remplace par le même volume de sérum physiologique. Pour chaque prélèvement, 50 µl sont ajoutés dans un tube où se trouvent 5 ml de Tryptone-sel (dilution 10-2). La solution de Tryptone-sel employée dans les exemples 3 et 4 est préparée par dissolution de 1 g de tryptone et de 8,5 g de NaCl dans 1000 ml d'eau distillée.At t o and at t o + 24 hours, a sample is taken in each vial: 0.2 ml of aqueous phase is taken from each vial (after stopping the stirring and decantation), which is replaced by the same volume of physiological saline. For each sample, 50 .mu.l are added to a tube containing 5 ml of Tryptone-salt (10 -2 dilution). The Tryptone-salt solution used in Examples 3 and 4 is prepared by dissolving 1 g of tryptone and 8.5 g of NaCl in 1000 ml of distilled water.

    Après homogénéisation, on effectue des dilutions en cascade jusqu'à 10-4 (10-6 pour le témoin) avec du sérum physiologique.After homogenization, cascade dilutions up to 10 -4 (10 -6 for the control) are carried out with physiological saline.

    Pour le comptage des bactéries, on étale alors 100 µl de chaque dilution sur milieu gélose PCA (« plate count agar »). La gélose PCA est préparée par mélange de 2,5 g d'extrait de levure, 5 g de tryptone, 1 g de glucose, 15 g d'agar et 1000 ml d'eau distillée.For counting the bacteria, 100 μl of each dilution PCA agar medium ("flat count agar"). PCA agar is prepared by mixing 2.5 g of yeast extract, 5 g of tryptone, 1 g of glucose, 15 g of agar and 1000 ml distilled water.

    Les boítes sont laissées une nuit couvercle vers le haut pour bien imprégner le milieu puis incubées 24h à 37°C. Le comptage des bactéries est effectué conformément à la norme ASTM E1259-94.The boxes are left overnight cover up to impregnate well the medium then incubated 24h at 37 ° C. Bacteria count is performed according to ASTM E1259-94.

    Les résultats obtenus sont les suivants :The results obtained are as follows:

    La concentration initiale à to dans chaque flacon est de 2,9.108 cfu/ml. The initial concentration at t o in each vial is 2.9 × 10 8 cfu / ml.

    Pour l'échantillon ne comprenant pas d'additif A, la concentration en bactéries au bout de 24 heures est de 103 cfu/ml. Pour l'échantillon comprenant l'additif A, la concentration en bactéries au bout de 24 heures est inférieure à 10 cfu/ml, c'est-à-dire quasi-nulle.For the sample containing no additive A, the concentration of bacteria after 24 hours is 10 3 cfu / ml. For the sample comprising additive A, the concentration of bacteria after 24 hours is less than 10 cfu / ml, that is to say almost zero.

    Exemple 4Example 4

    Cet exemple illustre l'effet fongicide d'un additif A selon l'invention sur une composition d'hydrocarbures classique.This example illustrates the fungicidal effect of an additive A according to the invention on a conventional hydrocarbon composition.

    L'additif A utilisé est identique à celui de l'exemple 1. La souche de moisissure utilisée est Hormoconis resinae (ATCC20495). La veille de l'inoculation, cette moisissure est cultivée sur boíte de Pétri, avec un temps d'incubation de 24 heures à 30°C.The additive A used is identical to that of Example 1. The mold strain used is Hormoconis resinae (ATCC20495). The day before inoculation, this mold is grown on a petri dish, with a 24 hour incubation time at 30 ° C.

    Deux compositions d'hydrocarbures sont préparées de la manière suivante :Two hydrocarbon compositions are prepared as follows:

    On prélève 2 échantillons de 300 g de coupe C que l'on place dans des flacons de 1000 ml en verre brun. On ajoute l'additif A avec les concentrations suivantes : 0 (témoin, conforme à l'art antérieur), 533 ppm (selon l'invention). Les flacons sont fermés de façon non hermétique. Les contenus de chaque flacon sont agités à l'aide d'un barreau magnétique, à température ambiante.2 samples of 300 g of cut C are taken and placed in 1000 ml bottles in brown glass. Additive A is added with the concentrations following: 0 (control, according to the prior art), 533 ppm (according to the invention). The vials are closed in a non-hermetic manner. The contents of each bottle are stirred with a magnetic bar at room temperature.

    L'inoculation des deux échantillons est réalisée à to de la manière suivante : on introduit 5 ml de sérum physiologique dans la boite de Pétri contenant les colonies, et on frotte légèrement afin de détacher les spores. On effectue ensuite un dénombrement au microscope à l'aide d'une cellule de Malassez. La concentration est de 2,2.107 spores/ml. Après dilution convenable de cette suspension dans les deux échantillons d'hydrocarbures, la concentration obtenue dans chaque flacon à to est de 5.103 cfu/ml.The inoculation of the two samples is carried out at t o in the following manner: 5 ml of physiological saline are introduced into the Petri dish containing the colonies, and lightly rubbed in order to detach the spores. An enumeration is then carried out under a microscope using a Malassez cell. The concentration is 2.2.10 7 spores / ml. After appropriate dilution of this suspension in the two hydrocarbon samples, the concentration obtained in each vial at t o is 5.10 3 cfu / ml.

    Des prélèvements sont effectués dans chacun des deux flacons, à intervalles de temps réguliers (à to, to + 24 heures, to + 48 heures, to + 72 heures, to + 7 jours). Pour chaque prélèvement, on prélève 0,2 ml de phase aqueuse dans chaque fiole (après arrêt de l'agitation et décantation) que l'on remplace par le même volume de sérum physiologique. Pour chaque prélèvement, 50 µl sont ajoutés dans un tube où se trouvent 5 ml de Tryptone-sel (dilution 10-2). Après homogénéisation, on effectue des dilutions en cascade jusqu'à 10-4 (10-6 pour le témoin) avec du sérum physiologique.Samples are taken from each of the two vials at regular time intervals (at t o , t o + 24 h, t o + 48 h, t o + 72 h, t o + 7 days). For each sample, 0.2 ml of aqueous phase is taken from each vial (after stopping the stirring and decantation) which is replaced by the same volume of physiological saline. For each sample, 50 .mu.l are added to a tube containing 5 ml of Tryptone-salt (10 -2 dilution). After homogenization, cascade dilutions up to 10 -4 (10 -6 for the control) are carried out with physiological saline.

    Pour le comptage, on étale alors 100 µl de chaque dilution sur milieu Sabouraud - chloramphénicol glucosé. Ce milieu est préparé par mélange de 10 g de peptone mycologique, 40 g de glucose, 0,1 g de chloramphénicol, 15 g d'agar et 1000 ml d'eau distillée. For the counting, 100 .mu.l of each dilution are then spread on medium Sabouraud - Chloramphenicol glucose. This medium is prepared by mixing 10 g of mycological peptone, 40 g of glucose, 0.1 g of chloramphenicol, 15 g of agar and 1000 ml of distilled water.

    Les boítes sont laissées une nuit couvercle vers le haut pour bien imprégner le milieu puis incubées 3 jours à 30°C. Le comptage des moisissures est effectué conformément à la norme ASTM E1259-94.The boxes are left overnight cover up to impregnate well the medium and then incubated for 3 days at 30 ° C. The count of molds is done according to ASTM E1259-94.

    Les résultats obtenus sont les suivants : Concentration en additif A 0 ppm 533 ppm Concentration H. resinae à t0 (cfu/ml) 5.103 5.103 Concentration H. resinae à t0 + 24 heures (cfu/ml) 3.103 4,9.102 Concentration H. resinae à t0 + 48 heures (cfu/ml) 7,1.102 1,1.102 Concentration H. resinae à t0 + 72 heures (cfu/ml) 1,8.103 1,1.102 Concentration H. resinae à t0 + 7 jours (cfu/ml) 1,2.103 40 The results obtained are as follows: Concentration of additive A 0 ppm 533 ppm Concentration H. resinae at t 0 (cfu / ml) 5.10 3 5.10 3 Concentration H. resinae at t 0 + 24 hours (cfu / ml) 3.10 3 4.9.10 2 Concentration H. resinae at t 0 + 48 hours (cfu / ml) 7.1.10 2 1.10 2 H. resinae concentration at t 0 + 72 hours (cfu / ml) 1.8.10 3 1.10 2 Concentration H. resinae at t 0 + 7 days (cfu / ml) 1,2,10 3 40

    Ces résultats démontrent clairement l'effet de l'additif A sur la prolifération des moisissures dans les coupes d'hydrocarbures : dans l'échantillon conforme à l'invention (contenant 533 ppm d'additif A), la concentration en moisissures diminue régulièrement, pour devenir quasi-nulle au bout de 7 jours.These results clearly demonstrate the effect of additive A on proliferation molds in hydrocarbon cuts: in the sample conforming to the invention (containing 533 ppm of additive A), the concentration of mold decreases regularly, to become almost zero after 7 days.

    Claims (23)

    Composition d'hydrocarbures comprenant une proportion majeure d'au moins une coupe d'hydrocarbures liquides, choisis parmi les carburants ou combustibles, caractérisée en ce qu'elle comprend de 1 à 2000 ppm masse d'au moins un additif de formule (I) ci-après :
    Figure 00170001
       dans laquelle le cycle cyclopentane est saturé ou insaturé , et
       R1, R2, R3, identiques ou différents, sont choisis parmi l'hydrogène et les radicaux hydrocarbonés comprenant de 1 à 10 atomes de carbone et comportant éventuellement un ou plusieurs hétéroatomes.    Hydrocarbon composition comprising a major proportion of at least one liquid hydrocarbon fraction, chosen from fuels, characterized in that it comprises from 1 to 2000 ppm by weight of at least one additive of formula (I) below:
    Figure 00170001
    wherein the cyclopentane ring is saturated or unsaturated, and
    R1, R2, R3, which may be identical or different, are chosen from hydrogen and hydrocarbon radicals comprising from 1 to 10 carbon atoms and optionally comprising one or more heteroatoms.         Composition d'hydrocarbures selon la revendication précédente, caractérisée en ce que l'additif est choisi parmi les composés de formule (I) dans laquelle R1 et R2, identiques ou différents, sont choisis parmi : l'hydrogène les radicaux alkylcarboxylate de formule R-COO les radicaux alkylcarbonyle de formule R-C=O les radicaux alcoxy de formule R-O    avec R radical hydrocarboné, saturé ou insaturé, comportant de 1 à 4 atomes de carbone, linéaire ou ramifié.Hydrocarbon composition according to the preceding claim, characterized in that the additive is chosen from compounds of formula (I) in which R1 and R2, which are identical or different, are chosen from: hydrogen the alkylcarboxylate radicals of formula R-COO alkylcarbonyl radicals of formula RC = O alkoxy radicals of formula RO with R saturated or unsaturated hydrocarbon-based radical containing from 1 to 4 carbon atoms, linear or branched. Composition d'hydrocarbures selon l'une quelconque des revendications précédentes, caractérisée en ce que R3 est choisi parmi l'hydrogène et les radicaux alkylcarboxylate de formule R'-COO avec R' radical alkyle en C1 à C4, linéaire ou ramifié.Hydrocarbon composition according to any one of the preceding claims, characterized in that R3 is chosen from hydrogen and alkylcarboxylate radicals of formula R'-COO with R 'linear or branched C1-C4 alkyl radical. Composition d'hydrocarbures selon l'une quelconque des revendications précédentes, caractérisée en ce que R1 ou R2 est l'hydrogène.Hydrocarbon composition according to any one of the preceding claims, characterized in that R1 or R2 is hydrogen. Composition d'hydrocarbures selon l'une quelconque des revendications précédentes, caractérisée en ce que R3 est l'hydrogène. Hydrocarbon composition according to any one of the preceding claims, characterized in that R3 is hydrogen. Composition d'hydrocarbures selon l'une quelconque des revendications précédentes, caractérisée en ce que R1 est choisi parmi les radicaux alkylcarboxylate de formule R'-COO avec R' radical alkyle en C1 à C4, linéaire ou ramifié.Hydrocarbon composition according to any one of the preceding claims, characterized in that R1 is chosen from alkylcarboxylate radicals of formula R'-COO with R 'linear or branched C1-C4 alkyl radical. Composition d'hydrocarbures selon l'une quelconque des revendications précédentes, caractérisée en ce que l'additif de formule (I) est employé en combinaison avec au moins un autre additif réodorant.Hydrocarbon composition according to any one of the preceding claims, characterized in that the additive of formula (I) is used in combination with at least one other resurfacing additive. Composition d'hydrocarbures selon la revendications précédente, caractérisée en ce que l'additif réodorant est choisi parmi : les aldéhydes aliphatiques et aromatiques ; les esters aliphatiques et aromatiques ; les hydroxydes ; les cétones ; les huiles essentielles ; et leurs mélanges. Hydrocarbon composition according to the preceding claim, characterized in that the deodorant additive is chosen from: aliphatic and aromatic aldehydes; aliphatic and aromatic esters; hydroxides; ketones; essential oils ; and their mixtures. Composition d'hydrocarbures selon l'une quelconque des revendications précédentes, caractérisée en ce que l'on emploie comme coupe d'hydrocarbures au moins une coupe essence, une coupe distillat ou une coupe essentiellement paraffinique ou un mélange de telles coupes.Hydrocarbon composition according to any one of the preceding claims, characterized in that at least one petrol cut, a distillate cut or an essentially paraffinic cut or a mixture of such cuts is employed as the hydrocarbon cut. Composition d'hydrocarbures selon l'une quelconque des revendications précédentes, caractérisée en ce que la composition d'hydrocarbures selon l'invention comprend au moins une coupe distillat.Hydrocarbon composition according to any one of the preceding claims, characterized in that the hydrocarbon composition according to the invention comprises at least one distillate cut. Composition d'hydrocarbures selon l'une quelconque des revendications précédentes, caractérisée en ce qu'elle est un carburant diesel.Hydrocarbon composition according to one of the preceding claims, characterized in that it is a diesel fuel. Composition d'hydrocarbures selon la revendication précédente, caractérisée en ce que sa teneur en soufre selon la norme EN 590 est inférieure ou égale à 50 ppm masse, de préférence inférieure ou égale à 10 ppm masse.Hydrocarbon composition according to the preceding claim, characterized in that its sulfur content according to EN 590 is less than or equal to 50 ppm by weight, preferably less than or equal to 10 ppm by weight. Composition d'hydrocarbures selon l'une quelconque des revendications 1 à 10, caractérisée en ce qu'elle est un fuel oil domestique.Hydrocarbon composition according to any one of Claims 1 to 10, characterized in that it is a domestic fuel oil. Composition d'hydrocarbures selon l'une quelconque des revendications 11 à 13 , caractérisée en ce qu'elle comprend un ou plusieurs additifs de lubrifiance ou d'anti-usure, tels que les acides gras et leurs dérivés ester ou amide, les acides carboxyliques mono- et polycycliques et leurs dérivés ester ou amide, notamment les acides gras comportant de 10 à 22 atomes de carbone et leurs dérivés amides, leur dérivés esters (esters de monoalcools, esters de polyols, esters partiels de polyols) par exemple les esters d'acide oléique, d'acide linoléique, le monooléate de glycérol, le caprate d'éthyle.Hydrocarbon composition according to any one of Claims 11 to 13, characterized in that it comprises one or more lubricity or anti-wear additives, such as fatty acids and their ester or amide derivatives, carboxylic acids mono- and polycyclic and their ester or amide derivatives, especially fatty acids containing 10 to 22 carbon atoms and their amide derivatives, their ester derivatives (monoalcohol esters, polyol esters, partial esters of polyols), for example oleic acid, linoleic acid, glycerol monooleate, ethyl caprate. Procédé de préparation d'une composition d'hydrocarbures présentant une odeur améliorée, comprenant le mélange de tout ou partie des hydrocarbures avec au moins un additif de formule (I) selon l'une quelconque des revendications 1 à 6.Process for the preparation of a hydrocarbon composition having an improved odor, including mixing all or part of the hydrocarbons with at least one additive of formula (I) according to any one of claims 1 to 6. Procédé selon la revendication précédente, caractérisé en ce que l'additif de formule (I) est incorporé à la composition d'hydrocarbures sous forme d'une composition parfumée comprenant l'additif de formule (I) en mélange avec d'autres additifs réodorants et éventuellement un solvant organique.Process according to the preceding claim, characterized in that the additive of formula (I) is incorporated in the hydrocarbon composition in the form of a perfume composition comprising the additive of formula (I) mixed with other additive additives and optionally an organic solvent. Procédé selon l'une quelconque des revendications 15 et 16, caractérisé en ce que le l'additif de formule (I), seul ou sous forme de composition parfumée, est dans un premier temps mélangé à tout ou partie des autres additifs que doit contenir la composition d'hydrocarbures, formant ainsi une composition d'additifs, puis, dans un deuxième temps, cette composition d'additifs est incorporée par simple mélange dans la composition d'hydrocarbures.Process according to either of Claims 15 and 16, characterized in that the additive of formula (I), alone or in the form of a perfume composition, is initially mixed with all or part of the other additives that must be contained in it the hydrocarbon composition, thus forming an additive composition, then, in a second step, this additive composition is incorporated by simple mixing in the hydrocarbon composition. Composition d'additifs pour carburant diesel, contenant : de 5 à 50% masse d'au moins un additif détergent ; de 0 à 60% masse d'au moins un additif procétane ; de 0 à 20% masse d'au moins un additif de filtrabilité ; de 0,1 à 20% masse d'au moins un additif de formule (I) selon l'une quelconque des revendications 1 à 6, ou de composition parfumée contenant un tel additif. Additive composition for diesel fuel, containing: from 5 to 50% by weight of at least one detergent additive; from 0 to 60% by weight of at least one procetane additive; from 0 to 20% by weight of at least one filterability additive; from 0.1 to 20% by weight of at least one additive of formula (I) according to any one of claims 1 to 6, or of perfume composition containing such an additive. Composition d'additifs pour fuel oil domestique, contenant : de 5 à 60% masse d'au moins un agent promoteur de combustion ; de 1 à 20% masse d'au moins un additif antioxydant ; de 5 à 20% masse d'au moins un additif de point d'écoulement ; de 0,1 à 20% masse d'au moins un additif de formule (I) selon l'une quelconque des revendications 1 à 6, ou de composition parfumée contenant un tel additif. Additive composition for domestic fuel oil, containing: from 5 to 60% by weight of at least one combustion promoter; from 1 to 20% by weight of at least one antioxidant additive; from 5 to 20% by weight of at least one pour point additive; from 0.1 to 20% by weight of at least one additive of formula (I) according to any one of claims 1 to 6, or of perfume composition containing such an additive. Méthode pour améliorer l'odeur des compositions d'hydrocarbures choisies parmi les carburants essence, les carburants diesels et les fuel oil domestiques, comprenant l'ajout à tout ou partie des hydrocarbures d'au moins un composé de formule (I) selon l'une quelconque des revendications 1 à 6, seul ou en mélange avec d'autres additifs réodorants.Method for improving the odor of hydrocarbon compositions selected from petrol fuels, diesel fuels and fuel oil including the addition to all or part of the hydrocarbons of at least one compound of formula (I) according to any one of claims 1 to 6, alone or in mixed with other additives. Méthode pour éliminer les bactéries et/ou les champignons dans les compositions d'hydrocarbures ou prévenir leur apparition dans de telles compositions, cette méthode comprenant l'ajout à tout ou partie des hydrocarbures d'au moins un composé de formule (I) selon l'une quelconque des revendications 1 à 6.Method for removing bacteria and / or fungi in hydrocarbon compositions or prevent their occurrence in such compositions, this method comprising the addition to all or part of the hydrocarbons of at least one compound of formula (I) according to any one of claims 1 to 6. Utilisation d'au moins un composé de formule (I) selon l'une quelconque des revendications 1 à 6, seul ou en mélange avec d'autres additifs réodorants, pour améliorer l'odeur des compositions d'hydrocarbures choisies parmi les carburants essence, les carburants diesels et les fuel oil domestiques.Use of at least one compound of formula (I) according to one of any of claims 1 to 6, alone or in admixture with other additives deodorants, to improve the odor of the hydrocarbon compositions chosen from petrol fuels, diesel fuels and domestic fuel oils. Utilisation d'au moins un composé de formule (I) selon l'une quelconque des revendications 1 à 6, seul ou en mélange avec d'autres additifs réodorants, pour éliminer les bactéries et/ou les champignons dans les compositions d'hydrocarbures ou prévenir leur apparition dans de telles compositions.Use of at least one compound of formula (I) according to one of any of claims 1 to 6, alone or in admixture with other additives deodorants, to eliminate bacteria and / or fungi in the hydrocarbon compositions or prevent their occurrence in such compositions.
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    EP1591514B1 (en) 2018-06-06
    FR2869621A1 (en) 2005-11-04
    PL1591514T3 (en) 2018-12-31
    EP1591514A3 (en) 2008-04-09

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