CN1125461A - Method and plant for solvent-free microwave extraction of natural products - Google Patents
Method and plant for solvent-free microwave extraction of natural products Download PDFInfo
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- CN1125461A CN1125461A CN94192507.2A CN94192507A CN1125461A CN 1125461 A CN1125461 A CN 1125461A CN 94192507 A CN94192507 A CN 94192507A CN 1125461 A CN1125461 A CN 1125461A
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/027—Recovery of volatiles by distillation or stripping
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- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
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- Extraction Or Liquid Replacement (AREA)
- Fats And Perfumes (AREA)
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Abstract
A microwave extraction method involves the steps of placing biological material in an enclosure without any solvent whatsoever and exposing the solvent-free biological material to microwave radiation to free at least some of the natural product, and then separating any residual biological material from the extracted natural product. Additionally, the microwave extraction method involves the steps of applying reduced pressure in the enclosure during the microwave radiation stage and heating the enclosure during at least most of the microwave radiation stage to compensate for the temperature drop resulting from water evaporation from the biological material.
Description
The present invention relates to from the field of biological substance extraction of natural products, particularly (but non-being confined to from plant) extracts the field of this series products from plant.
Extraction of natural products can adopt various methodologies from biological substance, their available one or more extraction solvents, and it is concrete that with where rule decides according to used biological substance and from the person's character of this material institute extracted products.Should be noted in the discussion above that taking which kind of extraction liquid usually is to decide on the technology of implementing to obtain this product.Like this, the coagulum that is formed by volatile compound or wax, fat and non-volatile product, thermosetting adhesive, oleoresin etc. generally are to obtain in the presence of at least a organic solvent.Perfume oil then generally uses wet distillation (water distillation) and/or mechanical means to obtain mainly by the compound formation of volatile aromatic.
For example take the physical method of fragmentation and/or squeezing and so on usually and without solvent or water distillation, can carry out the extraction from contain oil production, extraction of essential from lemon peel also can extract Oils,glyceridic,cod-liver.Except the implementation cost of this class technology was very low, the extracted products (with the biological substance after the extraction) that obtains with it did not contain residual solvent, and therefore need not follow-up processing eliminates this class residue.
But, there are many products from the crude substance that contains this product, not extract by these class methods, require to use the abstraction technique that organic solvent is arranged.Use this class technology, the product material that extract diffuses into solvent and is dissolved in wherein.But in order to concentrate extract, this just need isolate extracted products from solvent.Under the condition that has solvent to exist, it is influential to the extraction yield that some parameters are arranged, and these parameters are meant:
-be extracted the solubleness of product in selected solvent,
-be extracted the diffusion of product in the solid substrate of used biological substance.
By changing the concentration of service temperature or solvent for use, can work to above-mentioned first parameter.
In addition, also can be before extraction step or its simultaneously, second parameter applied effect.For example, biological substance is carried out can improving the diffusion that is extracted the product material greatly by crushing, enzymolysis or the dry again preprocessing operation that constitutes.Also can when extracting operation, apply effect, as heat or stir biological substance.For example in the prior art, the method for known employing acoustic energy is with the ultrasonic mixture that is used for biological substance and solvent, to promote that extract enters solvent.Biological substance is local to produce cavity because the mechanical wave energy of ultrasonic formation makes, thereby makes this material heating, further discharges extract.
Prior art also proposes to carry out microwave irradiation to promote therefrom extracted products to biological substance.Microwave is known to the effect of biological substance.This class hertzian wave is optionally absorbed by the medium of high dielectric constant, thereby for biological substance, promptly mainly by water, promptly basically by vascular tissue and gland tissue, is then absorbed by vesicle specifically for plant.At soak time, radiating capacity is converted into heat energy, so optionally heats the microwave absorbing part of biological substance.
European patent EP 0398798 has disclosed the technology of microwave extracting product from biological substance, comprises the following steps:
-segmentation has the biological substance (Mentha arvensis L. syn.M.haplocalyxBrig, lovage, cdear or garlic) of microwave absorbing dispersed component (water),
-be placed on microwave or partially transparent the material of segmentation, and the absorption of microwave is less than in the solvent (as hexane ethanol or methyl chloride) of dispersed component
-make the material of segmentation and the mixture of solvent formation accept microwave irradiation, the material (better being solvent to be arranged together) that segments with heating extracts soluble product,
-the biological substance of separating residual from solvent,
-recovery extracted products.
Though this technology extraction yield described in EP 0398798 patent increases, and can not overcome the top mentioned shortcoming that still has residual solvent in extract.
Should be noted that in the prior art, proposed to extract perfume oil from biological substance with the method for solvent-free microwave irradiation.
In " Flavour and Fragrance Journal " Volume Four, in " Mircrowave Oven Extraction of an Essential Oil " literary composition in 43-44 pages, disclosed technology with the volatile oil of microwave heating extraction Lippia sidoides.According to this technology, 30-40 gram plant samples are placed in the solvent-free flask in the microwave oven, allow microwave exposure 5 minutes.The airflow that used flask can make volatile oil be come from the outside is entrained.
Though the extraction time of this method is effectively carried out required time much shorter more than the water distillation extraction, its main drawback is the energy that needs input very high, and this makes what economic worth is this method do not have.
The method of all microwave extraction of natural products described in the document, can only be used in relative microwave power quality very little through finished biological substance.General power range is 10,000W-20,000W/kg biological substance.The peak power of the microwave transmission device of 2450MHz frequency is 6KW in market.In order to make these methods can be used for technical scale, then they must be fit to operate continuously, and the result can only the few material of the amount of being treated at the spatial given position in mid power microwave source front.
One object of the present invention is exactly the method for microwave extraction of natural products that proposes not have the shortcoming of art methods.
Specifically, an object of the present invention is to provide and a kind ofly extract, thereby do not contained the method for the extract of residual solvent without solvent.
A further object of the present invention is to be the processed biological substance of specified rate, and a kind of very method of macro-energy of importing that do not require is provided.
Another object of the present invention provides the device of this method of enforcement.
The present invention relates to the method for at least a natural product of microwave extracting from biological substance, described method comprises:
-described biological substance is placed in the solvent-free container,
-allow described biological substance in described container accept microwave exposure, make at least a portion water evaporation that is contained in the described biological substance, the result, the cellularstructure of the described biological substance of riving, thus can discharge the described natural product of at least a portion,
-from the natural product of extraction, divide the residual biological substance of leaving away,
Described method is characterised in that it also comprises following complementary step:
-when carrying out the microwave irradiating step, in the ground decompression of described container discontinuous, so that the process that the biological substance cellularstructure that promotion is caused by microwave irradiating is rived,
-give described container heating in the main phase of carrying out the microwave irradiating step, descend from the temperature that the biological substance evaporation causes because of water with compensation,
The step of said vesse decompression and the step of container heating and the step of microwave irradiating are combined, and entrained the transporting of water vapour that described natural product just can be generated from biological substance promptly allows this natural product carry out the water distillation.
A kind of like this advantage of method is that it can carry out in all natural biological materials, though animal, plant or microorganism, as long as these materials contain at least 30% water.This method can be used to especially from plant, animal tissues, particularly fish, and algae, little-algae even may be extraction sesame oil essence from microorganism.Certainly, this kind biological substance is looked its character and may must be segmented operation earlier before the container of packing into, so that increase the surface-area that it is subjected to microwave irradiation.
Method of the present invention makes might be to being extracted the water distillation that product carries out, and be not the water by adding this moment, but with being contained in the interior moisture content of processed biological substance.Should be noted in the discussion above that this in this manual moisture is called as water of constitution, even biological substance to be processed has been dehydrated form, therefore the handy step of humidifying again and again also is like this to the situation that this material adds entry in advance.
Therefore, method of the present invention is to carry out microwave exposure and without extraction solvent, the cell content matter of this material is discharged to biological substance.For the purpose that the azeotropic that promotes this process and realization to be extracted product is overflowed, can make the container decompression.Decompression at first can increase the mechanical stress on the biological substance cell walls, secondly can increase the volatility of the azeotropic mixture for the treatment of that extraction product and water vapour form.According to the present invention, can compensate the temperature that causes owing to structure evaporation of water under low pressure to the heating of container and sharply descend.Such temperature descends the beneficial effect that microwave is produced can not be shown fully.
Method of the present invention has many advantages.
Except no solvent residue, to compare with common water distillation, method of the present invention can obtain the extract of same composition and identical extraction yield in the shorter time.Common water distillation time is generally in a few hours scopes, and decompression water distillation time of the present invention is in several minutes scopes.For some product, obtain a certain amount of extract, the comparable common water of method of the present invention distills fast ten times.
In addition, method of the present invention is than the extracting process that is aided with microwave in the prior art, and the energy of consumption is less.For same a kind of processed biological substance of same amount, energy required for the present invention also is less than the required energy of water distillating method.In the water distillation procedure, need heat to biological substance, and need add water, and the add-on of water can be ten times of biological amount.
At last, should be noted in the discussion above that the biological substance residue that obtains at last in the methods of the invention is a dried forms, because its contained water of constitution overflowed and be used to carry extraction product, and this method is not used extraneous water.Therefore, this residue is can be at an easy rate in addition broken with the method for heat, the recirculation use that acts as a fuel.
Be preferably, the step that the present invention is intermittently reduced pressure is decompression cycle to be carried out in the inside of described container handle.
According to a kind of variant method of the present invention, described from extract the biological substance step of separating residual comprise:
-freezing the water vapour that contains described extraction of natural products
The liquid mixture of the freezing gained of-decant,
-described extraction of natural products of separation and water from decant.
Though another advantage of the present invention is the product that obtains containing than common water distillating method the residuary water much less, but at least a portion water that obtains in the decantation steps is injected container, remain in the water distillation of crude substance in the biological substance residue, this still is favourable.
In addition, described heating steps should carry out being lower than under 100 ℃ the temperature.Should be noted that extraction for the product that under heat effect, can degenerate, this method be lower than be only under 75 ℃ of temperature favourable.
The frequency of the microwave that uses in the described microwave exposure step should equal 300MHz at least.But the frequency of utilization that should be noted in the discussion above that many countries is strict regulation very, as in France, has only 915MHz and 2450MHz frequency to can be used for producing the industrial equipments of microwave.
In addition, the power range of described microwave irradiating step is 100W to 10, the product of 000W/kg processing treatment.
According to a variant of the invention process method, described microwave exposure step is that described biological substance is being carried out carrying out under the churned mechanically condition.This stirring can increase the effect that biological substance is received in microwave irradiation.
The present invention also relates to implement the equipment of these class methods, comprising:
-device that produces microwave and the container with thermostatic control double wall be housed in inside;
-can regulate the heating unit of described thermostatic control double wall;
-the device that can in described container, reduce pressure;
-after extract leaves described container, to its device that reclaims.
Be preferably, the described device that reclaims extract is exactly that the water vapour that contains extract is carried out the refrigerated device.
The device that described equipment preferably will have the pressure that can make in the container to circulate and reduce pressure.
It is favourable that described container is equipped with whipping appts.
At last advantageously, described equipment has the device that the residuary water that can will reclaim obtains in the device of extract is carried out recirculation from described container.
The present invention and advantage thereof from following exemplary embodiment and with reference to accompanying drawing, just are easier to understand these figure:
-Fig. 1 is the synoptic diagram of present device.
-Fig. 2 represents that the device with Fig. 1 extracts the minty note essential oil in the first embodiment of the present invention, in variation and the biological substance variation of temperature according to container inner pressure;
-Fig. 3 represents the variation of the minty note essential oil yield that first embodiment obtains;
-Fig. 4 represents container inner pressure and biological substance variation of temperature in the comparing embodiment extraction minty note essential oil;
-Fig. 5 represents the variation of minty note essential oil yield in the comparing embodiment;
-Fig. 6 represents second embodiment of the invention extraction Salvia japonica Thunb. volatile oil, its container pressure and biological substance variation of temperature;
-Fig. 7 represents the variation of second embodiment of the invention extraction Salvia japonica Thunb. volatile oil yield.
Fig. 1 has represented a set of equipment of extraction of natural products from biological substance.In this covering device, the device 2 of the microwave of portion's generation within it is housed.Technical regulation, device 2 can be sent the microwave (please note that also usable frequency is the microwave generator of 915MHz, this frequency also is that France allows) that equals the 2450MHz frequency.
According to the present invention, container 1 at first with can be connected its device that reduces pressure 5, secondly be connected with the device 6 that is used for reclaiming by the microwave natural product that effect extracts to biological substance.Can make the device 5 that reduces pressure in container, can be any conventional equipment that is used for forming the partial vacuum effect in container, as pump or strainer glass air extractor.In the present invention, the device 6 that reclaims extracted products has the pipeline 11 that is contained in container 1 top, and being around in around it is the freezing plant 7 of spiral tube form, has cooling fluid to flow through in the spiral tube.
In order to strengthen container 1, with the temperature decline that the decompression of compensation vacuum pump causes, container 1 has the thermostatted control double wall 3 that is connected with heating unit 4.
Above-mentioned this complete equipment once was used for implementing the method for microwave extracting of the present invention, with volatile oil (embodiment 1) and the Salvia japonica Thunb. volatile oil (embodiment 3) of extraction peppermint.
The peppermint (Mentha piperita L., Hungary's kind) of 1kg 15% ridity is placed in the container 1.Set heating unit, make thermostatic control wall 3 produce about 70 ℃ temperature in container 1, start whipping appts, velocity of rotation is 40rpm.The power of microwave generating apparatus 2 is output as 1150W, and the power that reflects away becomes association between 170W and 220W.In the extracting operation that continues 15 minutes, real power absorbed thereby be 930-980W.
When extraction, pump 5 is used to pressure is dropped to 250 millibars.Reduced pressure one by one at 5 minutes, 10 minutes and 13 minutes.
In addition, the temperature of refrigerant is set to 5 ℃ in curling up pipe 7, with the vapour condensation of accelerating because of microwave the peppermint effect to be generated that contains volatile oil.
Fig. 2 has shown the variation of interior peppermint variation of temperature of container and pressure.Under microwave action, product temperature slowly changes to 75 ℃ from room temperature.In case when being extracted into partial vacuum (25mmHg) by pump 5 in the container, temperature just descends.But the reduction of temperature is immediately because of heating is compensated to container, so can not influence the effect of microwave to extraction.
Referring to Fig. 3, extract after 15 minutes and the decompression cycle 3 times, reclaim 31.52ml volatile oil (100 gram dry-matteies obtain 1.01ml perfume oil).
The peppermint residue remaining to microwave extracting operation back carried out the water distillation, the volatile oil that further obtains connect 50 milligrams less than.Therefore, the volatile oil yield of extracting process of the present invention has approached to extract degree completely from biological substance.
With gas-chromatography two kinds of volatile oil that the inventive method and common water distillating method obtain are done test relatively, find what big difference they do not have on composition.
With embodiment 1 identical operations condition under to handling with the peppermint of embodiment 1 same amount, different is that pump 2 is worked constantly and made the pressure in the container 1 all remain on 250 millibars in extracting operation.
The change of peppermint variation of temperature and container inner pressure as shown in Figure 4.
Referring to Fig. 5, the yield of volatile oil: 100 grams have only 0.2ml, promptly have only 1/5th of embodiment 1.After the microwave extracting operation, 1150 milligrams of volatile oil have been recovered to from the peppermint residue.These two kinds of results represent, in the inventive method, and the importance that decompression need intermittently be carried out in container.
The Salvia japonica Thunb. (Salvia officinalis L.) of 1kg25% ridity is placed in the container 1.Set heating unit, thermostatic control wall 3 is produced in container 1 be about 70 ℃ temperature, start whipping appts, speed is 40rpm.The power of microwave generating apparatus 2 is output as 1000W, and the power variation that reflects away is between 150W and 200W.In the extracting operation that continues 10 minutes, real power absorbed thereby be 800-850W.
When extraction, pump 5 is used to pressure is dropped to 250 millibars.After 3.5 minutes and 7 minutes, reduce pressure one by one.
In addition, the temperature of refrigerant is set to 7 ℃ in curling up pipe 7, with the vapour condensation of accelerating because of microwave the Salvia japonica Thunb. effect to be generated that contains volatile oil.
Fig. 6 has shown the variation of interior Salvia japonica Thunb. variation of temperature of container and pressure.
Referring to Fig. 7, extract after 10 minutes and the decompression cycle 2 times, reclaim 33.06ml volatile oil (100 gram dry-matteies obtain 2.55ml volatile oil).
The Salvia japonica Thunb. of same amount with the theoretical yield of common water distillating method be 100 restrain 2.77ml, this shows that the recoverable volatile oil of the inventive method accounts for more than 90% of perfume oil in the processed Salvia japonica Thunb..
The technical scheme that exemplifies of the present invention is not the scope that is used for dwindling it.Specifically, only otherwise deviate from framework of the present invention, can adopt different microwave frequencies, the time of microwave action is changeable, also can use and described technical scheme diverse ways separating and extracting thing from steam.
Claims (13)
1. the method for at least a natural product of microwave extracting from biological substance, described method comprises:
-described biological substance is placed in the container that solvent is not housed,
-the described biological substance in described container is carried out microwave exposure, make at least a portion water evaporation that is contained in the described biological substance, the result, the cellularstructure of the described biological substance of having rived, thus can discharge the described natural product of at least a portion,
-from the natural product that extracted, separate and remove residual biological substance,
Described method is characterised in that it also comprises following complementary step:
-carrying out microwave irradiating, during step, in the ground decompression of described container discontinuous, so that the cyto-architectural process of riving of biological substance that promotion is caused by microwave action,
-in the basic time of described microwave irradiating step, give described container heating, the temperature that causes because of water evaporates from biological substance with compensation descends,
To carry out the step of microwave irradiating, the step that reduces pressure in container and combine to the step of container heating has just carried out carrying out the water distillation under the condition that described natural product carries in the water vapour from biological substance.
2. method according to claim 1 is characterized in that, described depressurization steps comprises to the inside of container and carries out decompression cycle.
3. method according to claim 1 and 2 is characterized in that, described extract and residual biological substance separation steps is comprised:
-freezing the water vapour that contains the natural product of described extraction
The liquid mixture of the freezing gained of-decant,
-by decant with described extraction of natural products and water sepn.
4. method according to claim 3 is characterized in that, the water that at least a portion is obtained from described decantation steps injects container, so that the natural product of staying in the biological substance residue are carried out the water distillation.
5. according to the described method of one of claim 1-4, it is characterized in that described heating steps carries out being lower than under 100 ℃ of temperature.
6. according to the described method of one of claim 1-5, it is characterized in that the used microwave frequency of microwave exposure is at least 300MHz.
7. according to the described method of one of claim 1-6, it is characterized in that the power range of described microwave exposure step is the product that 100-1000W/kg is extracted processing.
8. according to the described method of one of claim 1-7, it is characterized in that described microwave exposure step is carrying out carrying out under the churned mechanically situation to biological substance.
9. implement the equipment of one of claim 1-8 described method, it is characterized in that it comprises:
-container (1) is equipped with the device (2) that produces microwave in it, it has thermostatted control double wall (3);
-can regulate the heating unit (4) of described thermostatic control double wall (3);
-the device (5) that can in described container, reduce pressure;
-after extract leaves described container, to its device (6) that further reclaims.
10. equipment according to claim 9 is characterized in that, the described device (6) that is used for reclaiming extract comprises freezing plant (7).
11., it is characterized in that it has device (8) according to claim 9 or 10 described equipment, it can allow the operation of described device (5) be to make pressure cycling decompression in the container.
12. according to the described equipment of one of claim 9-11, it is characterized in that, whipping appts (9) be housed in the described container.
13., it is characterized in that it comprises device (10) according to the described equipment of one of claim 9-12, it can make capable again the recycling of residuary water of the device gained that reclaims at the extract of discharging from described container (1).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR93/05810 | 1993-05-11 | ||
| FR9305810A FR2705035B1 (en) | 1993-05-11 | 1993-05-11 | Process and installation for solvent-free extraction of natural products by microwave. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1125461A true CN1125461A (en) | 1996-06-26 |
| CN1059920C CN1059920C (en) | 2000-12-27 |
Family
ID=9447117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94192507A Expired - Fee Related CN1059920C (en) | 1993-05-11 | 1994-05-10 | Method and plant for solvent-free microwave extraction of natural products |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0698076B1 (en) |
| JP (1) | JPH08512337A (en) |
| CN (1) | CN1059920C (en) |
| AT (1) | ATE162211T1 (en) |
| AU (1) | AU682035B2 (en) |
| BG (1) | BG62367B1 (en) |
| BR (1) | BR9406717A (en) |
| CA (1) | CA2161127C (en) |
| DE (1) | DE69407965T2 (en) |
| DK (1) | DK0698076T3 (en) |
| ES (1) | ES2114688T3 (en) |
| FR (1) | FR2705035B1 (en) |
| GR (1) | GR3026603T3 (en) |
| HU (1) | HU218708B (en) |
| RU (1) | RU2115700C1 (en) |
| WO (1) | WO1994026853A1 (en) |
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| CA1336968C (en) * | 1989-05-16 | 1995-09-12 | J. R. Jocelyn Pare | Microwave-assisted natural products extraction |
| SE9003593D0 (en) * | 1990-11-12 | 1990-11-12 | T G Owe Berg | PROCEDURE FOR CONVERSION OF HEATS TO WORK |
| DE69024961T2 (en) * | 1990-11-16 | 1996-08-14 | United Kingdom Government | Microwave separation of volatile oils and device therefor |
-
1993
- 1993-05-11 FR FR9305810A patent/FR2705035B1/en not_active Expired - Fee Related
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1994
- 1994-05-10 WO PCT/FR1994/000551 patent/WO1994026853A1/en active IP Right Grant
- 1994-05-10 CA CA002161127A patent/CA2161127C/en not_active Expired - Fee Related
- 1994-05-10 CN CN94192507A patent/CN1059920C/en not_active Expired - Fee Related
- 1994-05-10 EP EP94915607A patent/EP0698076B1/en not_active Expired - Lifetime
- 1994-05-10 ES ES94915607T patent/ES2114688T3/en not_active Expired - Lifetime
- 1994-05-10 AT AT94915607T patent/ATE162211T1/en not_active IP Right Cessation
- 1994-05-10 RU RU95122234A patent/RU2115700C1/en active
- 1994-05-10 BR BR9406717A patent/BR9406717A/en not_active IP Right Cessation
- 1994-05-10 DE DE69407965T patent/DE69407965T2/en not_active Expired - Lifetime
- 1994-05-10 JP JP6525060A patent/JPH08512337A/en not_active Ceased
- 1994-05-10 HU HU9503230A patent/HU218708B/en not_active IP Right Cessation
- 1994-05-10 AU AU67251/94A patent/AU682035B2/en not_active Ceased
- 1994-05-10 DK DK94915607T patent/DK0698076T3/en active
-
1995
- 1995-12-04 BG BG100187A patent/BG62367B1/en unknown
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1998
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| CN105213272B (en) * | 2015-11-09 | 2019-02-01 | 北京工商大学 | A kind of fresh and alive water of lavender and the preparation method and application thereof |
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2115700C1 (en) | 1998-07-20 |
| EP0698076B1 (en) | 1998-01-14 |
| CA2161127C (en) | 2005-09-27 |
| DE69407965T2 (en) | 1998-09-10 |
| GR3026603T3 (en) | 1998-07-31 |
| CN1059920C (en) | 2000-12-27 |
| BR9406717A (en) | 1996-02-06 |
| WO1994026853A1 (en) | 1994-11-24 |
| BG100187A (en) | 1996-05-31 |
| BG62367B1 (en) | 1999-09-30 |
| ES2114688T3 (en) | 1998-06-01 |
| JPH08512337A (en) | 1996-12-24 |
| HUT75578A (en) | 1997-05-28 |
| DK0698076T3 (en) | 1998-09-14 |
| FR2705035B1 (en) | 1995-08-04 |
| AU682035B2 (en) | 1997-09-18 |
| CA2161127A1 (en) | 1994-11-24 |
| HU218708B (en) | 2000-11-28 |
| AU6725194A (en) | 1994-12-12 |
| DE69407965D1 (en) | 1998-02-19 |
| HU9503230D0 (en) | 1996-01-29 |
| FR2705035A1 (en) | 1994-11-18 |
| EP0698076A1 (en) | 1996-02-28 |
| ATE162211T1 (en) | 1998-01-15 |
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