NZ199390A - Extracting vegetable wax form plant material (simmondsia species) - Google Patents
Extracting vegetable wax form plant material (simmondsia species)Info
- Publication number
- NZ199390A NZ199390A NZ199390A NZ19939081A NZ199390A NZ 199390 A NZ199390 A NZ 199390A NZ 199390 A NZ199390 A NZ 199390A NZ 19939081 A NZ19939081 A NZ 19939081A NZ 199390 A NZ199390 A NZ 199390A
- Authority
- NZ
- New Zealand
- Prior art keywords
- extraction
- separation
- pressure
- critical
- temperature
- Prior art date
Links
- 241000196324 Embryophyta Species 0.000 title claims description 7
- 241000221095 Simmondsia Species 0.000 title claims description 6
- 239000012178 vegetable wax Substances 0.000 title claims description 6
- 239000000463 material Substances 0.000 title description 3
- 238000000605 extraction Methods 0.000 claims description 41
- 238000000926 separation method Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 28
- 239000001993 wax Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 241000894007 species Species 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 10
- 239000001569 carbon dioxide Substances 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000221096 Simmondsia chinensis Species 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000004433 Simmondsia californica Nutrition 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- -1 CHF^ Chemical class 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000641 cold extrusion Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000001192 hot extrusion Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 239000012165 plant wax Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0203—Solvent extraction of solids with a supercritical fluid
-
- 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
- C11B11/00—Recovery or refining of other fatty substances, e.g. lanolin or waxes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Description
New Zealand Paient Spedficaiion for Paient Number 1 99390
1 9
3
0
.. i . 'W-11* i ' !T t)
Priority Dstc(s):
./J-2 i/J 01
Ccmpfets Spscsficalion FjJad: .. i..
.....iaea
is .mums
N.Z. No.
NEW ZEALAND
Patents Act 1953
COMPLETE SPECIFICATION
¥
[««V^
"PROCESS FOR THE SEPARATION OF VALUABLE MATTER FROM PLANT MATERIAL."
We, KALI-CHEMIE PHARMA GmbH, a Body Corporate organised under the laws of the Federal . Republic of Germany, of Postfach 220,
Hans-Buckler-Allee 20, D-3000 Hannover 1, Federal Republic of Germany do hereby declare the invention, for which pray that a Patent may be granted to us f and the method by which it is to be performed, to be particularly described in and by the following statement:-
~ 1 ~ (Followed by 1A.)
- i A
1 99390
This invention relates to a method for the separation of valuable substances from plant matter.
Fortyfive to fifty percent by weight of the total weight of fully ripened seed kernels of plants of the 5 species Simmondsia (Simmondsia chinensis and Simmondsia
California) consist of a fluid wax. This wax is a mixture of long-chain fatty acid esters, the acid component of which is formed from higher, straight chain acids and the alcohol component of which is formed from higher,
monovalvent alcohols. Thus it differs substantially from normal plant oils, which, as is known, are triglycerides of glycerol. Owing to its good stability it has a variety of uses, for example as a carrier or excipient for cosmetic or pharmaceutical formulations.
Methods used hitherto for the separation and isolation of the wax include cold or hot extrusion of the seed kernels, or the extraction of the wax with various solvents from the previously ground or compressed seed kernels.
Apart from the fact that with mechanical extrusion only approximately 60 to 70% of the wax content can be extracted, usual commercial qualities, which have been obtained by extrusion, still contain portions of cell matter.
N.Z. PATENT OFFICE
16DEC1983
199390
These portions of cell matter which are intrusive for many purposes, must be separated in further process steps. However, particular filtering methods, which use conventional filter media such as, for example, kieselguhr, 5 silica gel, fuller's earth or alumina, in fact yield a product, which is free of solid components, but these filtering methods have an adverse influence on the stability of the wax. Thus, waxes purified by filtration through active media quickly become rancid and unusable 10 when stored under normal conditions.
Methods of extraction of the wax components by means of solvents have not been used technically to date. Furthermore, products obtained in such a way still contain residues of solvent and without further purification 15 operations they are consequently unusable for cosmetic or pharmaceutical purposes.
According to the present invention there is provided a method for the separation of valuable substances from plant matter, wherein seed "kernels of species of Simmondsia 20 are subjected to extraction in an extraction stage by means of a gas under supercritical conditions, thereby to obtain a phase containing valuable substances, and wherein this phase is transferred into a separation stage, where separation of the valuable substances occurs by providing 25 or establishing subcritical conditions, whereby a substantially pure stable vegetable wax is obtained as the valuable substance, the gas being returned from the separation stage to the extraction stage.
W.2. PATENT OFRCE
-5 DEC 1983
9 93?
In general, any gas which is physiologically harmless, and which is chemically inert to the plant wax, can be used as the extraction medium; such gases include for example: carbon dioxide, various halogenated
hydrocarbons including, CHF^, CF3~CF3' CHC1=CF2,
cf2=ch2, cf3-ch3, chf2-ch3, chf2ci, cf3ci, cf2=cf2,
CF0C1_, CC1 -CHC10 and C_F , sulphur hexafluoride, nitrous Z Z 3 2 j o oxide, sulphur dioxide, and various hydrocarbons including ethane, ethene, propane, propene, etc. 10 Mixtures of two or more of such gases may be used but carbon dioxide is particularly preferred.
In the extraction stage the seed kernels are exposed to the extraction medium under conditions such that the gas is supercritical both as regards temperature and also as 15 regards pressure. The critical parameters of the gases mentioned above are well-known.
The temperature at which the extraction takes place is preferably in the range of from the critical temperature up to 50°C, preferably up to 20°C. above the critical 20 temperature, and the pressure is preferably in the range from the critical pressure up to 500 bar, preferably up to 350 bar above the critical pressure.
In the case where the extraction medium is carbon dioxide, the extraction is conveniently carried out at a 25 temperature in the range of from 31.3 to 80°C., preferably 31.3 to 50°C., and at a pressure in the range of from 72 to 600 bar, preferably 72 to 300 bar.
1 9 93 9
From the extraction stage, the phase containing the valuable matter is passed over into the separation stage in which separation of the valuable substances takes place by providing or establishing subcritical 5 conditions. The temperature at which the separation takes place is preferably in the range of from the critical temperature to 15°C. below the critical temperature, and the pressure is preferably in the range of from the critical pressure to 25 bar below the critical 10 pressure.
In the case where the extraction medium is carbon dioxide, the separation is conveniently carried out at a temperature in the range of 31.3°C. to 15°C. and at a pressure in the range from 72 to 45 bar. 15 By providing or establishing subcritical conditions in the separation stage, the solvent power of the extraction medium for the extracted valuable substances is reduced such that the latter separate in the separation stage from the extraction medium and can be carried off 20 during the extraction process, for example through a sluice, or after the extraction process has been completed. Any aqueous components which have also been separated during the extraction process form a separate phase in the separation stage and can be separated from the wax 25 without difficulty.
The extraction medium can be re-useid directly without any further purification requiring intensive work and energy, so that no additional emission problems arise. In order to be re-introduced into the extraction 5 stage, the extraction medium merely has to be converted into the supercritical state as regards temperature and pressure, i.e. the alteration in temperature and pressure which was made for separation is cancelled again.
The separated vegetable wax can be removed from the 10 separation stage after the extraction is completed if the present process is conducted as a batch process.
However, it is possible to remove the vegetable wax -e.g. via a sluice - if the present process is conducted as a continuous process. With both methods of 15 operation extraction periods of 1 to 12 hours, preferably 3 to 7 hours, are sufficient, to obtain the end product in the purity desired.
With the present method therefore it is possible to obtain the desired product in a short time, thereby 20 minimizing the overheads for apparatus, manpower and energy, and also to avoid any undue burden on the environment. The circulation of the extraction medium offers in particular the possibility of automating the process cycle and, consequently, of conducting the extraction 25 in a particularly economical way. The vegetable wax
1 9939
obtained can be supplied directly for utilization in foodstuffs, pharmaceutical or cosmetic products etc; however, it can also be hydrated and used as a hydrated product.
The invention will now be illustrated by the following
Examples in which specific process conditions are identified as follows:-
Extraction container: Pressure : P^
Temperature : t^
Separation container: Pressure :
Temperature : t^
Example 1
100 g. of previously ground seed kernels of Simmondsia are loaded into an extraction container and extracted with carbon dioxide gas under supercritical conditions; separation is effected in a separation container and the process conditions are:-
P^ : 200 bar
40°C.
50 bar
Extraction time
°C.
4 h
41 g. of a clear, light yellow wax are obtained and removed from the separation container; .in addition, 3.5 g. water are isolated. 55 g. of a pulverulent de-oiled product remain in the extraction container.
1 9939
- 7
The analysis of the wax was as follows:-
C38~
fluid ester approx.
%
C40~
fluid eister approx.
%
C42~
fluid ester approx.
50
%
C44~
fluid ester approx.
%
Example 2
100 g. of simmondsia seed kernels, stripped of the brown pellicle and ground, are loaded into the extraction container and extracted with carbon dioxide 10 gas under supercritical conditions, and separation is effected under subcritical conditions, the process conditions being:-
: 300 bar tx : 40°C.
P^ : 50 bar t2 : 20°C.
Extraction time : 4 h 40 g. of a clear, light yellow fatty acid ester-mixture are removed from the separation container. In addition 20 7.5 g. water are separated and 53 g. of a pulverulent residue remains in the extraction vessel.
Example 3
100 g. of ground seed kernels of the Simmondsia chinensis plant are treated with carbon dioxide gas under 25 supercritical conditions and separation is effected under subcritical conditions, the process conditions being:-
150 bar 50° C.
50 bar
° c-
Extraction time : 4 h
36 g. of a clear, light yellow wax are recovered in the separation container, and in addition 3.5 g. water are separated while 60 g. de-waxed base material remain as a residue in the extraction container.
199390
Claims (9)
1. A method for the separation from plant matter of a valuable vegetable substance in the form of a substantially stable pure/wax, wherein seed kernels of species of Simmondsia are subjected to extraction in an extraction stage by means of a gas under supercritical conditions, thereby to obtain a phase containing a valuable substance, and wherein this phase is transferred into a separation stage, where separation of the valuable substance occurs by providing or establishing subcritical conditions in the gas, whereby a said valuable substance is obtained, the gas being returned from the separation stage to the extraction stage.
2. A method as claimed in Claim 1 wherein the gas is carbon d ioxide.
3. A method as claimed in Claim 1 or 2, wherein the temperature at which the extraction takes place is from the critical temperature up to 50°C above the critical temperature.
4. A method as claimed in any one of Claims 1 to 3, wherein the temperature at which the extraction takes place is from the critical temperature up to 20°C above the critical temperature.
5. A method as claimed in any one of Claims 1 to 4, wherein the temperature at which the separation takes place is from the critical temperature to 15°C below the critical temperature. 10 -
6. A method as claimed in any one of Claims 1 to 5, wherein the pressure at which the extraction takes place is from the critical pressure up to 500 bar above the critical pressure. 5
7. A method as claimed in any one of Claims 1 to 6, wherein the pressure at which the extraction takes place is from the critical pressure up to 350 bar above the critical pressure.
8. A method as claimed in any one of Claims 1 to 7, 10 wherein the pressure at which the separation takes place is from the critical pressure to 25 bar below the critical pressure. 15 in any one of the foregoing Examples. 10. Vegetable wax obtained from seed kernels of species of SiTnmondsia by the method claimed in any preceding claim. a
9. A method for the separation of/valuable substance according to claim 1 from plant matter!, substantially as hereinbefore described KALI-CHEMIE PHARMA GmbH By Their Attorneys HENRY HUGHES LIMITED
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813101025 DE3101025A1 (en) | 1981-01-15 | 1981-01-15 | METHOD FOR ISOLATING VALUABLES FROM PLANT MATERIAL |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ199390A true NZ199390A (en) | 1984-05-31 |
Family
ID=6122639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ199390A NZ199390A (en) | 1981-01-15 | 1981-12-23 | Extracting vegetable wax form plant material (simmondsia species) |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS57145195A (en) |
| AT (1) | AT372608B (en) |
| AU (1) | AU7951282A (en) |
| BE (1) | BE891781A (en) |
| DD (1) | DD201915A5 (en) |
| DE (1) | DE3101025A1 (en) |
| DK (1) | DK12982A (en) |
| ES (1) | ES8306788A1 (en) |
| FI (1) | FI820074L (en) |
| FR (1) | FR2497823A1 (en) |
| GB (1) | GB2091292B (en) |
| GR (1) | GR75832B (en) |
| IL (1) | IL64587A0 (en) |
| IT (1) | IT1195293B (en) |
| NL (1) | NL8105301A (en) |
| NO (1) | NO820104L (en) |
| NZ (1) | NZ199390A (en) |
| PT (1) | PT74018B (en) |
| SE (1) | SE8200069L (en) |
| ZA (1) | ZA817997B (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4466923A (en) * | 1982-04-01 | 1984-08-21 | The United States Of America As Represented By The Secretary Of Agriculture | Supercritical CO2 extraction of lipids from lipid-containing materials |
| DE3322968A1 (en) * | 1983-06-25 | 1985-01-10 | Fried. Krupp Gmbh, 4300 Essen | METHOD AND DEVICE FOR PRODUCING FATS AND OILS |
| DE3424614A1 (en) * | 1983-07-05 | 1985-01-17 | Kuraray Co., Ltd., Kurashiki, Okayama | METHOD FOR PRODUCING AN EXTRACT |
| DE3414977C2 (en) * | 1984-04-19 | 1992-01-09 | Hopfenextraktion HVG Barth, Raiser & Co, 8069 Wolnzach | Process for the extraction of solids with compressed carbon dioxide |
| JPH0816233B2 (en) * | 1991-08-30 | 1996-02-21 | 三井物産株式会社 | Process for producing purified propolis and O / W emulsion containing purified propolis component |
| FR2799660B1 (en) * | 1999-10-19 | 2002-01-18 | Hitex | SUPERCRITICAL FLUID EXTRACTION PROCESS |
| US7091366B2 (en) | 2003-09-25 | 2006-08-15 | Thar Technologies, Inc. | Recovery of residual specialty oil |
| FR2865644B1 (en) * | 2004-01-29 | 2007-10-19 | Oreal | PROCESS FOR PREPARING A COSMETIC PROCESSING COMPOSITION FROM PRESSURIZED FLUID AND ESTERS |
| GB0502337D0 (en) * | 2005-02-04 | 2005-03-16 | Univ York | Isolation and fractionation of waxes from plants |
| DE102005037210A1 (en) * | 2005-08-06 | 2007-02-08 | Degussa Ag | Process for the extraction of fruit waxes |
| DE102018001205A1 (en) | 2018-02-14 | 2019-08-14 | Sven Miric | Method and apparatus for extracting and / or concentrating lipophilic molecules by means of liquid or supercritical carbon dioxide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2127596A1 (en) * | 1971-06-03 | 1972-12-21 | Hag Ag, 2800 Bremen | Process for the production of vegetable fats and oils. |
-
1981
- 1981-01-15 DE DE19813101025 patent/DE3101025A1/en not_active Withdrawn
- 1981-11-18 ZA ZA817997A patent/ZA817997B/en unknown
- 1981-11-20 PT PT74018A patent/PT74018B/en unknown
- 1981-11-23 NL NL8105301A patent/NL8105301A/en not_active Application Discontinuation
- 1981-11-24 IT IT25240/81A patent/IT1195293B/en active
- 1981-12-03 FR FR8122666A patent/FR2497823A1/en not_active Withdrawn
- 1981-12-09 DD DD81235587A patent/DD201915A5/en unknown
- 1981-12-09 GB GB8137117A patent/GB2091292B/en not_active Expired
- 1981-12-18 IL IL64587A patent/IL64587A0/en unknown
- 1981-12-23 NZ NZ199390A patent/NZ199390A/en unknown
- 1981-12-29 AT AT0560081A patent/AT372608B/en not_active IP Right Cessation
-
1982
- 1982-01-08 SE SE8200069A patent/SE8200069L/en not_active Application Discontinuation
- 1982-01-11 FI FI820074A patent/FI820074L/en not_active Application Discontinuation
- 1982-01-13 JP JP57002916A patent/JPS57145195A/en active Pending
- 1982-01-13 GR GR66999A patent/GR75832B/el unknown
- 1982-01-13 BE BE0/207056A patent/BE891781A/en not_active IP Right Cessation
- 1982-01-14 AU AU79512/82A patent/AU7951282A/en not_active Abandoned
- 1982-01-14 ES ES508714A patent/ES8306788A1/en not_active Expired
- 1982-01-14 NO NO820104A patent/NO820104L/en unknown
- 1982-01-14 DK DK12982A patent/DK12982A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AT372608B (en) | 1983-10-25 |
| JPS57145195A (en) | 1982-09-08 |
| NO820104L (en) | 1982-07-16 |
| GB2091292B (en) | 1984-03-21 |
| BE891781A (en) | 1982-04-30 |
| FI820074L (en) | 1982-07-16 |
| ZA817997B (en) | 1982-10-27 |
| IT8125240A0 (en) | 1981-11-24 |
| DD201915A5 (en) | 1983-08-17 |
| ES508714A0 (en) | 1983-06-01 |
| DK12982A (en) | 1982-07-16 |
| FR2497823A1 (en) | 1982-07-16 |
| NL8105301A (en) | 1982-08-02 |
| ATA560081A (en) | 1983-03-15 |
| ES8306788A1 (en) | 1983-06-01 |
| PT74018A (en) | 1981-12-01 |
| GB2091292A (en) | 1982-07-28 |
| AU7951282A (en) | 1982-07-22 |
| IL64587A0 (en) | 1982-03-31 |
| IT1195293B (en) | 1988-10-12 |
| GR75832B (en) | 1984-08-02 |
| PT74018B (en) | 1983-06-20 |
| DE3101025A1 (en) | 1982-08-26 |
| SE8200069L (en) | 1982-07-16 |
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