EP0081231B1 - Procédé pour la production des substances aromatiques à partir d'un extrait de tabac - Google Patents

Procédé pour la production des substances aromatiques à partir d'un extrait de tabac Download PDF

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Publication number
EP0081231B1
EP0081231B1 EP82111300A EP82111300A EP0081231B1 EP 0081231 B1 EP0081231 B1 EP 0081231B1 EP 82111300 A EP82111300 A EP 82111300A EP 82111300 A EP82111300 A EP 82111300A EP 0081231 B1 EP0081231 B1 EP 0081231B1
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EP
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Prior art keywords
tobacco
extraction
pressure
process according
tank
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Expired
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EP82111300A
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German (de)
English (en)
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EP0081231A3 (en
EP0081231A2 (fr
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Adam Dr. Müller
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Individual
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Individual
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Priority claimed from DE19813148335 external-priority patent/DE3148335C2/de
Priority claimed from DE19823218760 external-priority patent/DE3218760A1/de
Application filed by Individual filed Critical Individual
Priority to BR8302980A priority Critical patent/BR8302980A/pt
Publication of EP0081231A2 publication Critical patent/EP0081231A2/fr
Publication of EP0081231A3 publication Critical patent/EP0081231A3/de
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Publication of EP0081231B1 publication Critical patent/EP0081231B1/fr
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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts

Definitions

  • the invention relates to a method for obtaining aroma substances from a tobacco extract according to the patent claims.
  • the new product is a clear tobacco aroma oil, free of polyphenols, resins and waxes, with a reduced (reduced) nicotine content of 5 to 50% relative (based on the tobacco from which the tobacco aroma oil is derived) and with that for Typical tobacco smell used in each case of starting tobacco.
  • the process according to the invention effects the separation of clear tobacco aroma oil from tobacco extract.
  • the flavoring of tobacco plays a special role in the manufacture of tobacco products. Attempts to partially or wholly obtain the tobacco aroma oil typical of the respective tobacco from aroma-strong tobacco or tobacco waste in order to add it to other, low-aroma tobacco of the same provenance have so far failed because an absolute (clear) tobacco aroma oil free of resins and waxes with reduced nicotine content.
  • DE-A-2128779 describes a process for obtaining aroma substances and converting the aroma precursors from tobacco by extracting the tobacco with one or more solvents which are in the eluotropic range between trichlorethylene and ethyl acetate and from the extract obtained the aroma precursors are activated by a heat treatment between 110 and 180 ° C.
  • the aroma products obtained by this process represent a wax-like, resinous mass which contains all waxes and resins as well as polyphenols and almost all nicotine of the starting product.
  • DE-A-2142 205 describes a method for the selective, aroma-preserving extraction of nicotine from tobacco in that in the first stage the aroma is extracted from the dry tobacco by treatment with dry, supercritical gases (e.g. CO2), which is then temporarily remains in the separating container B until the tobacco in the container A has been removed from the nicotine by means of moist CO 2 by a second process stage, which is then separated out in the container D. In a third stage of the process, the flavorings in container B are mixed with e.g. B. supercritical C0 2 solved, returned to container A and deposited there on the tobacco.
  • dry, supercritical gases e.g. CO2
  • This process is expensive in terms of tobacco aroma extraction and exploitation and is inefficient because the product obtained in the first stage is not a clear liquid tobacco aroma oil that can be separated from resins and waxes, but is a paste that contains almost all unwanted waxes and resins of the starting product and undesirable ones Includes polyphenols.
  • these wax and resinous substances prevent the even distribution and aroma transfer when rearomatizing a tobacco to be loaded.
  • One of the disadvantages of the polyphenols is that they impair the smoky taste.
  • DE-A-2 844 781 describes a process for the extractive treatment of plant and animal material, including the processing of tobacco using a two-component solvent, such as. B. 93 mole percent CO 2 + 7 mole percent ethanol or 94 mole percent CO 2 + 6 mole percent butane.
  • the two-phase mixture is intended to ensure that, for. B. the adducts formed during organic solvent extraction and changes in the processed material can be avoided.
  • Working with C0 2 under supercritical pressure conditions alone is required to achieve sufficient degrees of extraction - pressures of over 150 bar. According to the process of DE-A-2 844 781, these disadvantages are to be avoided if the CO 2 used for the extraction has certain amounts, for. B. alcoholic solvents can be added as entrainer.
  • the object of the present invention is to provide a process for obtaining a clear, absolute tobacco aroma oil, which contains almost all the aroma substances of the starting product qualitatively and quantitatively, is free from resins, waxes and polyphenols and whose nicotine content - compared to the starting product - is greatly reduced .
  • Tobacco in the sense of the present invention are fermented tobacco leaves, stems, stems or dust as well as tobacco waste.
  • tobacco primary extract is one with customary organic solvents, in particular benzene, toluene, methanol, ethanol, n-propanol, methyl ethyl acetate, diethyl ether, acetone, n-propane, n-hexane, cyclohexane, petroleum ether, dichloromethane or trichloromethane, or extract prepared with mixtures of these solvents.
  • a primary extract in the sense of the present invention is also a CO 2 extract, ie extract produced with the help of C0 2 as a solvent.
  • Adsorbents for the purposes of the present invention are all common adsorbents, in particular activated carbon, aluminum oxide, magnesium oxide, sodium aluminum silicate, bleaching earth, bentonite, silica gel, diatomaceous earth, zeolitic molecular sieves etc.
  • Tobacco aroma oil in the sense of the present invention is a tobacco aromatic, oily liquid which is absolutely clear at normal temperature and free of resins and waxes, free of polyphenols, with a reduced nicotine content of 5 to 50% relative, (in particular 10 to 40% relative) on the tobacco from which the tobacco extract comes - which shows no clouding or precipitation when 95% by weight ethanol is added.
  • the preparation of the tobacco primary extract used according to the invention consists in particular in extracting the tobacco in one of the abovementioned solvents or (in the case of organic solvents) in a solvent mixture.
  • 1 part by weight of pre-shredded tobacco is preferably extracted with about 3 to 30 parts by weight of one of the solvents mentioned (preferably CO 2 , n-hexane or dichloromethane).
  • the primary extraction is carried out for at least 10 minutes and at most 10 hours, preferably for 1 to 5 hours.
  • the primary extraction takes place under normal pressure conditions. If organic solvents are used, the primary extraction takes place under normal pressure conditions. If CO 2 is used in the primary extraction, the pressure and temperature conditions in the extraction container and separating container, as well as the extraction time and CO 2 flow rate, are identical to those which are specified below in connection with the (single-stage) secondary extraction.
  • the evaporation is preferably carried out under reduced pressure, particularly preferably at about 15 torr. In the case of the use of C0 2 , the evaporation takes place in the separating container, as already stated above, under the pressure and temperature conditions as specified below for the (single-stage) secondary extraction.
  • a tobacco primary extract obtained in this way contains u. a. Polyphenols, resins / waxes, nicotine and, as the inventor has determined, is in an easily accessible form which is particularly suitable for the subsequent secondary extraction (with CO2).
  • the tobacco primary extract obtained is then intensively mixed according to the invention with an adsorbent until there is a uniform distribution between the extract and the adsorbent.
  • adsorbent sodium aluminum silicate, bentonite, magnesium oxide, or zeolitic molecular sieves
  • Adsorbent is variable and can vary depending on the consistency of the extract, the density and particle size of the adsorbent and the desired consistency of the mixed product can be adjusted. In general, a mixture ratio of extract: adsorbent between 1: 0.1 to 1:10 is sufficient; preference is given to a powdery extract mixture with a mixing ratio of extract: adsorbent of 1: 0.3 to 1: 6.
  • the extract / adsorbent mixture should not fall below the ratio 1: 0.1, because the adsorbent used according to the invention, the dissolving of the aroma substances in the subsequent secondary extraction with CO 2 (in the extraction container) and the separation in the separation container as easily separable from resins and waxes, clear absolute tobacco aroma oil significantly influenced.
  • a mixing ratio of more than 1:10 also gives. a good detachment and separation of the tobacco aroma oil, although a larger pressure vessel volume has to be accepted.
  • the mixture of primary extract and adsorbent is treated according to the invention in a first pressure vessel (extraction vessel), preferably high-pressure vessel, with CO 2 under certain pressure and temperature conditions until all the aroma substances in the second pressure vessel (separator vessel) downstream of the extraction vessel are considered to be slightly of resins and waxes separable, oily liquid.
  • This secondary extraction with CO 2 is achieved by supercritically (> 73 bar and> 31.3 ° C) or in relation to the CO 2 used for the extraction of the extract / adsorbent mixture with respect to pressure and temperature Pressure and temperature subcritical «73 bar and ⁇ 31.3 ° C) or with regard to pressure supercritical (> 73 bar) and with regard to temperature subcritical ( ⁇ 31.3 ° C).
  • pressures from 85 to 250 bar and temperatures from + 35 ° C to + 90 ° C are preferred.
  • pressures from 25 to 70 bar and temperatures from + 5 ° C to + 25 ° C are preferred.
  • pressures from 85 to 200 bar and temperatures from + 10 ° C to + 30 ° C are preferred.
  • an additional CO z - can be used between the claimed primary extraction and the claimed secondary extraction. Extraction step at low temperatures are interposed.
  • the extract obtained in the primary extraction and mixed with the adsorbent is treated in advance at CO z extraction temperatures of ⁇ 25 ° C to + 5 ° C and CO 2 extraction pressures of about 20 to 25 bar;
  • the expansion in the separating tank takes place under subcritical pressure and temperature conditions, with a separation (of nicotine) in the separating tank at temperatures of about + 15 ° C to + 30 ° C and at pressures of about 2 to 15 bar is preferred.
  • An extraction time of 0.5 to 2 hours, preferably about 1 hour, and a CO 2 flow rate of 5 to 50 kg / hour, preferably 10 to 30 kg / hour, are sufficient.
  • the deposition conditions in the expansion tank are decisive for the quality and quantity of the product obtained according to the invention.
  • the relaxation pressures and relaxation temperatures are expediently in the subcritical range of C0 2 (subcritical pressure / subcritical temperature). Pressures of 45 to 65 bar and temperatures of 15 to 30 ° C are preferred; pressures of about 50 to 55 bar and temperatures of 20 to 25 ° C. are particularly preferred.
  • the separation in the expansion tank is preferably carried out with simultaneous pressure and temperature lowering than the pressure and temperature conditions prevailing in the extraction tank.
  • the amount of the extraction vessel by flowing C0 2 and the duration of the flow are for the inventive Ver f AH rentician significantly.
  • Treatment times totaling 0.5 to 8 hours, preferably 1 to 5 hours, particularly preferably 2 to 4 hours are expedient;
  • a total amount of CO 2 is expedient from 0.3 to 35 kg / hour, preferably 3 to 30 kg / hour, particularly preferably 5 to 15 kg / hour, based on 1 kg of untreated tobacco.
  • a special characteristic of the tobacco aromatic oil obtained according to the invention is also that it has the tobacco smell typical of the starting tobacco used in each case. This characteristic clearly distinguishes it from all tobacco extracts known to date, because none of the conventional tobacco extracts made it possible to produce the typical smell of the respective starting tobacco. Based on this characteristic feature of the tobacco extract obtained according to the invention, it can be assumed that its material composition is completely new compared to the prior art.
  • the present invention is the first, starting from a product (tobacco primary extract). which contains flavors, polyphenols, nicotine, resins, waxes and other substances side by side, achieves a separation and recovery of the tobacco flavor as a clear and absolute oil, and this. with measures that are easy to carry out and a particularly efficient result.
  • the tobacco ingredients which are obtained by primary extraction according to the procedure according to the invention, behave in a mixture with a powdery adsorbent and subsequent secondary extraction (with CO 2 ) with respect to their viscosity, their solubility and separation ratios very different than the same ingredients that only the primary extraction (also the C0 2 7 Primary extraction), e.g. B. from tobacco leaves.
  • Aroma oils obtained in a conventional manner were only produced by steam distillation on a laboratory scale.
  • the oils obtained were of numerous foreign smells, such as. B. chamomile, caraway, peppermint, valerian and amyl alcohol, which are probably caused by artifact formation.
  • the yield of such tobacco oils was about 0.1 to 0.2%.
  • the tobacco aroma oil obtained according to the invention which has the typical and pure smell of the starting tobacco used in each case, is clearly different from this. So smells like B. the Havana tobacco flavored oil obtained from Havana tobacco, Kentucky tobacco flavored oil obtained from Kentucky tobacco.
  • aromatic oils obtained from Virginia, Orient or Burley tobacco show the very typical and pure smell of the respective tobacco type. Because of this particular characteristic, which is clearly different from the prior art, it should be noted that the tobacco aromatic oil obtained according to the invention is completely new in its material composition compared to the products of the prior art.
  • the tobacco aromatic oil obtained in the manner according to the invention is free from foreign odors, free from polyphenols, resins and waxes, has a reduced nicotine content which is only 5 to 50% relative to the tobacco leaves used, and is obtained in yields of 0.8 to 2%. Get 5% (absolute oil).
  • the tobacco aroma oil obtained according to the invention can be used to aromatize tobacco or tobacco products, this aromatization being able to be carried out either directly by tobacco or by aromatizing porous carrier material or tobacco adhesive material.
  • the tobacco aromatic oil obtained according to the invention is not only suitable for flavoring weak-flavored tobacco or reconstituted tobacco by means of sauces (“casing”), but is also particularly suitable as a “top flavor”.
  • porous carrier materials which are in contact with tobacco or tobacco products.
  • porous support materials can e.g. B. in the form of pieces of paper or clay, dummies.
  • inner packaging material e.g. boxes, bags, etc.
  • a further embodiment of flavoring using the tobacco aromatic oil according to the invention is also the addition to adhesive material for tobacco products.
  • adhesives as are commonly used for tobacco products, e.g. B. Adhesives for cigar wrappers, cigarette paper, etc.
  • the tobacco aroma oil obtained according to the invention can be used to decisively influence any fluctuations that occur during production (quality differences or other differences in the smoky taste) of the tobacco.
  • the amount of tobacco aromatic oil used to flavor tobacco or tobacco products can vary depending on the nature of the tobacco and the desired flavoring.
  • Havana tobacco aroma oil obtained according to the invention is preferably used for loading 25 to 100, particularly preferably 40 to 60 mg of tobacco aroma oil per kg of tobacco, ie. H. 25 to 100 ppm, preferably 40 to 60 ppm.
  • the high productivity and intensity that can be achieved with the product obtained according to the invention is particularly promoted by the fact that a tobacco aromatic oil that is free of resin, polyphenol and wax is present.
  • This particular quality of the tobacco aroma oil also represents a particularly characteristic and novel feature compared to the prior art.
  • Liquid C0 2 is removed from the tank 1 in the subcritical pressure and temperature state.
  • the C0 2 is set to the desired subcritical or supercritical temperature and, with the aid of the high pressure pump 3, the desired supercritical or subcritical pressure.
  • the CO 2 enters the extraction container 4, where the extraction of the mixture of primary extract and adsorbent takes place.
  • the extraction container 4 is filled and emptied with product discontinuously by opening and closing the head opening after each extraction.
  • the pressure prevailing in the extraction container is determined with the pressure sensor 14.
  • the separation of the tobacco constituents dissolved in the CO 2 is initiated by the pressure control valve 8 and supported by lowering the temperature in the heat exchanger 9.
  • the extracted tobacco components separate into a clear tobacco aroma oil and a waxy, resinous nicotine product, which are either removed continuously through the valve 17 or after the extraction has ended by opening the tank 10.
  • opening the valve 5 also relieves the pressure of the extraction side of the device.
  • the C0 2 emerging from the expansion tank 10 during the extraction is recirculated via line 11.
  • the device can be controlled by hand or by means of the electrical control device 12, the inputs of which are the temperature measured with a temperature sensor 13 in the extraction container 4, the pressure measured with pressure sensors 14 and 15, and the CO Z streams emerging from the pressure containers 4 and 10 as well as the flow rate measured with the flow meter 7.
  • the pressure control valve 8 and also the cooling capacity in the heat exchanger 9 are set as a function of these measured values.
  • Havana tobacco water content 6.5%, nicotine content 1.27%) are crushed in a knife mill and exhaustively extracted in 10 liters of dichloromethane and the solvent is evaporated off under a vacuum of 15 torr.
  • the mixture was treated with CO 2 in a closed high-pressure extraction container at a pressure of 230 bar and a temperature of 65 ° C. for 120 minutes.
  • the pressure on the relaxation side was 50 bar, the temperature 24 ° C.
  • the flow rate of C0 2 is 6 kg / hour.
  • the yield of clear, absolute tobacco aroma oil was 2.25% of the tobacco used.
  • the nicotine content was 19.92%, which is 35% relative to the nicotine present in the tobacco.
  • the yield of the resin / wax deposit was 1.76%, the nicotine content 43% absolute, which is 60% relative to the nicotine present in the tobacco.
  • the tobacco aroma oil obtained was free from resins and waxes and showed no precipitation and no clouding when 95% by weight ethanol was added.
  • this mixture is subjected to a secondary extraction with CO 2 .
  • the tobacco aromatic oil obtained was free from resins, waxes and polyphenols and had the smell typical of Kentucky tobacco. No turbidity occurred when 95% by weight ethanol was added.
  • the flow rate of C0 2 is 25 kg / hour.
  • the flow rate of CO 2 was 15 kg / hour.
  • the yield of clear tobacco aroma oil was 1.55% of the tobacco used, the nicotine content was 9.55% absolute, which is 5.2% relative to the nicotine present in the tobacco.
  • the tobacco aroma oil obtained was free from resins and waxes and showed no precipitation and no clouding when 95% by weight ethanol was added.
  • the pressure on the relaxation side was 50 bar, the temperature + 20 ° C.
  • the flow rate of CO 2 is 10 kg / hour.
  • the yield of clear tobacco aroma oil was 1.2% of the tobacco used, the nicotine content was 23.2% absolute, which is 19.17% relative to the nicotine present in the tobacco.
  • the resin / wax precipitate had a nicotine content of 57.2% absolute, which is 31.5% relative to the nicotine present in the tobacco.
  • the tobacco aroma oil obtained was free from resins and waxes and showed no precipitation and no clouding when 95% by weight ethanol was added.
  • tobacco aroma oil was obtained from the same Havana tobacco - as used in Example 1 ⁇ 0.14% clear and in 95% by weight - ethanol which is not cloudy.
  • the nicotine content of the aromatic oil was 0%.
  • Tobacco C was clearly preferred and is best suited for flavoring.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Fats And Perfumes (AREA)
  • Extraction Or Liquid Replacement (AREA)

Claims (12)

1. Procédé pour la production de substances aromatiques à partir d'un extrait de tabac pouvant être obtenu avec un solvant, appelé extrait primaire, ce solvant étant choisi parmi le benzène, le toluène, le méthanol, l'éthanol, le n-propanol, le méthyléthylacétate, le diéthyléther, l'acétone, le propane, le n-hexane, le cyclohexane, l'éther de pétrole, le dichlorométhane, le trichlorométhane ou des mélanges de ces solvants ou du dioxyde de carbone, caractérisé en ce que l'on mélange l'extrait primaire avec un agent d'adsorption, ce mélange étant soumis à une extraction secondaire avec du C02 dans un réservoir fermé sous pression, appelé réservoir d'extraction, et en ce que dans un deuxième réservoir fermé sous pression, appelé réservoir de séparation, on obtient une essence aromatique de tabac limpide ayant une teneur réduite en nicotine et pouvant être facilement séparée des résines et cires.
2. Procédé selon la revendication précédente, caractérisé en ce qu'en tant qu'agent d'adsorption lors de l'extraction secondaire, on met en oeuvre de l'oxyde de magnésium, du charbon actif, de l'oxyde d'aluminium, du silicate de sodium et d'aluminium, de l'argile décolorante. de la bentonite, du gel de silice, du kieselguhr ou un tamis moléculaire zéolitique.
3. Procédé selon l'une des revendications précédentes, caractérisé en ce que l'on utilise un rapport de mélange entre l'extrait primaire et l'agent d'adsorption de 1 : 0,1 jusqu'à 1 : 10.
4. Procédé selon l'une des revendications précédentes, caractérisé en ce que pour l'extraction secondaire avec du CO2 dans le réservoir d'extraction, on opère à des conditions de pression et de température surcritiques, à des conditions de pression et de température sous-critiques ou à des conditions de pression surcritique et de température sous-critique.
5. Procédé selon l'une des revendications précédentes, caractérisé en ce que lors de l'extraction secondaire on procède à la détente avec du CO2 dans le réservoir de séparation sous des conditions de pression et de température sous-critiques.
6. Procédé selon l'une des revendications précédentes, caractérisé en ce que l'on produit une essence aromatique de tabac dont la teneur en nicotine est relativement réduite à 5 jusqu'à 50 % par rapport à la teneur en nicotine des feuilles de tabac avant l'extraction primaire.
7. Procédé selon l'une des revendications précédentes, caractérisé en ce que pour la réduction de la nicotine dans l'essence aromatique de tabac relativement jusqu'à 5 à 10 % par rapport à la teneur en nicotine des feuilles de tabac avant l'extraction primaire, on effectue l'extraction secondaire avec du C02 en deux étapes :
a. une première étape d'extraction avec du C02 à une température de ―25° C jusqu'à + 5° C et à une pression d'environ 20 à 25 bars dans le réservoir d'extraction,
b. une deuxième étape d'extraction avec du C02 par augmentation subséquente de la pression et de la température jusqu'à une valeur supérieure à 25 bars et supérieure à 5° C dans le réservoir d'extraction.
8. Procédé selon la revendication 7, caractérisé en ce que dans le réservoir de séparation, on procède à la détente sous des conditions de pression et de températures sous-critiques.
9. Procédé selon l'une des revendications précédentes, caractérisé en ce que l'on effectue l'extraction secondaire avec du C02 pendant 0,5 à 8 heures.
10. Procédé selon l'une des revendications précédentes, caractérisé en ce que lors de l'extraction secondaire, on met en oeuvre du C02 en une quantité de 0,3 à 35 kg/heure, rapportée à 1 kg de tabac, dont provient l'extrait de tabac.
11. Procédé selon l'une des revendications précédentes, caractérisé en ce que le produit obtenu lors de l'extraction secondaire dans le réservoir de séparation est séparé par filtration en résines et en cires d'une part, et en essence aromatique limpide de tabac d'autre part.
EP82111300A 1981-12-07 1982-12-07 Procédé pour la production des substances aromatiques à partir d'un extrait de tabac Expired EP0081231B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BR8302980A BR8302980A (pt) 1982-12-07 1983-06-06 Processo para a obtencao de substancias aromaticas de um estrato de tabaco,oleo aromatico de tabaco claro e emprego

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19813148335 DE3148335C2 (de) 1981-12-07 1981-12-07 Verfahren zur Gewinnung von Aromastoffen aus Tabak und deren Verwendung
DE3148335 1981-12-07
DE3218760 1982-05-18
DE19823218760 DE3218760A1 (de) 1982-05-18 1982-05-18 Klares tabak-aromaoel, sowie verfahren zu seiner gewinnung aus einem tabakextrakt und dessen verwendung

Publications (3)

Publication Number Publication Date
EP0081231A2 EP0081231A2 (fr) 1983-06-15
EP0081231A3 EP0081231A3 (en) 1985-06-19
EP0081231B1 true EP0081231B1 (fr) 1988-09-07

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EP82111300A Expired EP0081231B1 (fr) 1981-12-07 1982-12-07 Procédé pour la production des substances aromatiques à partir d'un extrait de tabac

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US (1) US4506682A (fr)
EP (1) EP0081231B1 (fr)
KR (1) KR880000170B1 (fr)
AU (1) AU555181B2 (fr)
DE (1) DE3278987D1 (fr)
DK (1) DK528082A (fr)
GB (1) GB2111371B (fr)
IE (1) IE53724B1 (fr)
IN (1) IN158943B (fr)

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WO2024201300A1 (fr) 2023-03-30 2024-10-03 Rai Strategic Holdings, Inc. Composition de précurseur d'aérosol comprenant un ester de monomenthyle

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KR880000170B1 (ko) 1988-03-12
AU555181B2 (en) 1986-09-18
IN158943B (fr) 1987-02-21
KR840002624A (ko) 1984-07-16
DE3278987D1 (en) 1988-10-13
GB2111371A (en) 1983-07-06
IE822901L (en) 1983-06-07
DK528082A (da) 1983-06-08
AU9118582A (en) 1983-06-16
EP0081231A3 (en) 1985-06-19
IE53724B1 (en) 1989-01-18
EP0081231A2 (fr) 1983-06-15
GB2111371B (en) 1985-09-11
US4506682A (en) 1985-03-26

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