EP0144934B1 - Produit à fumer contenant de l'oxyde N' de nicotine - Google Patents
Produit à fumer contenant de l'oxyde N' de nicotine Download PDFInfo
- Publication number
- EP0144934B1 EP0144934B1 EP84114573A EP84114573A EP0144934B1 EP 0144934 B1 EP0144934 B1 EP 0144934B1 EP 84114573 A EP84114573 A EP 84114573A EP 84114573 A EP84114573 A EP 84114573A EP 0144934 B1 EP0144934 B1 EP 0144934B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- nicotine
- oxide
- trans
- cis
- oxidation
- 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.)
- Expired
Links
- 230000000391 smoking effect Effects 0.000 title claims description 14
- RWFBQHICRCUQJJ-NUHJPDEHSA-N (S)-nicotine N(1')-oxide Chemical compound C[N+]1([O-])CCC[C@H]1C1=CC=CN=C1 RWFBQHICRCUQJJ-NUHJPDEHSA-N 0.000 title claims description 11
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 40
- 229960002715 nicotine Drugs 0.000 claims description 40
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 30
- 241000208125 Nicotiana Species 0.000 claims description 27
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 27
- RWFBQHICRCUQJJ-JQWIXIFHSA-N trans-(S)-nicotine N(1')-oxide Chemical compound C[N@+]1([O-])CCC[C@H]1C1=CC=CN=C1 RWFBQHICRCUQJJ-JQWIXIFHSA-N 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 16
- 238000007254 oxidation reaction Methods 0.000 claims description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- RWFBQHICRCUQJJ-CMPLNLGQSA-N cis-(S)-nicotine N(1')-oxide Chemical compound C[N@@+]1([O-])CCC[C@H]1C1=CC=CN=C1 RWFBQHICRCUQJJ-CMPLNLGQSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000002808 molecular sieve Substances 0.000 claims description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 14
- 235000019504 cigarettes Nutrition 0.000 description 13
- 239000000047 product Substances 0.000 description 9
- 239000000779 smoke Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000019506 cigar Nutrition 0.000 description 3
- RWFBQHICRCUQJJ-UHFFFAOYSA-N nicotine N(1')-oxide Chemical class C[N+]1([O-])CCCC1C1=CC=CN=C1 RWFBQHICRCUQJJ-UHFFFAOYSA-N 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 150000004967 organic peroxy acids Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- YHXKVHQFWVYXIC-JTQLQIEISA-N (S)-nicotine 1-N-oxide Chemical compound CN1CCC[C@H]1C1=CC=C[N+]([O-])=C1 YHXKVHQFWVYXIC-JTQLQIEISA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
Classifications
-
- 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
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
Definitions
- the invention relates to a smoking product, in particular tobacco with or without wrapping material, containing nicotine N'-oxide.
- the invention is based on the knowledge that the cis isomer of nicotine N'-oxide leads to a considerable deterioration in the taste of smoke. Accordingly, the invention is primarily directed to a smoke product, the smoke of which has an increased nicotine content due to the addition of nicotine N'-oxide, wherein the above-mentioned taste impairment of the smoke by the cis isomer can be avoided.
- smoking product means cut tobacco, pipe tobacco, cigarettes, cigarillos or cigars made of tobacco with or without added non-tobacco materials and / or reconstituted tobacco.
- the smoking product of the invention can be made with or without wrapping material, and the wrapping material used can be cigarette paper, cigars or cigarillo wrappers made of tobacco or non-tobacco materials.
- the smoking product of the invention contains the nicotine-N-oxide as trans-nicotine-N'-oxide, which is free or essentially free of cis-nicotine-N'-oxide or a content of at most 10% by weight of the cis -Isomers, in an amount up to 5 wt .-%, based on the smoke product dry weight.
- the trans-nicotine N'-oxide to be used according to the invention which is free or essentially free of cis-nicotine N'-oxide or has a content of at most 10% by weight of the cis isomer, can be used in tobacco or contained non-tobacco materials and / or the wrapping materials, if any, z. B. the cigarette paper or the cigar or cigarillo wrappers made of tobacco and / or non-tobacco materials.
- the addition is advantageously carried out on the finished tobacco material, for. B. in the form of an aqueous solution, or on the finished wrapping material, for. B. in an alcoholic or aqueous-alcoholic solution.
- the invention is further directed to a process for the production of trans-nicotine N'-oxide which is free or substantially free of cis-nicotine-N'-oxide, particularly for use as an additive to smoking products of the invention.
- the invention is therefore further directed to a process for the production of trans-nicotine N'-oxide, which is free or essentially free of cis-nicotine N'-oxide, requires short reaction times, and in which only auxiliaries which are unobjectionable under food law come into use.
- the process of the invention is characterized in that the oxidation is carried out in the presence of catalytic amounts of non-oxidizing inorganic and / or organic acids with a pK value of less than 5.
- the reaction temperature during the reaction should in any case be as low as possible, since higher reaction temperatures favor the formation of decomposition products and the cis isomer, although the latter only to a small extent.
- the reaction temperature should never be above 90 ° C, otherwise explosive decomposition of the hydrogen peroxide can occur.
- Monocarboxylic, dicarboxylic or polycarboxylic acids and their hydroxy, keto or unsaturated derivatives are particularly suitable as catalytically active acids with a pKa value of less than 5.
- the reaction of nicotine with hydrogen peroxide is preferably carried out in essentially equimolar amounts, hydrogen peroxide being initially introduced and nicotine being added dropwise; the reverse procedure is also possible.
- an oxidizing agent it is expedient to add commercially available hydrogen peroxide in the form of a 30-50% aqueous solution.
- the acids used as catalysts are preferably used in an amount of 10-150, in particular 20-100 mmol per mole of nicotine.
- the oxidation mixture obtained during the oxidation is dewatered.
- the dewatering can preferably be carried out by azeotropic distillation using n-propanol as the azeotropic dewatering agent. Remaining traces of water can be removed from the reaction mixture dried in this way using a molecular sieve (pore size 4A).
- the trans-nicotine N'-oxide crystallizes out of the dry oxidation mixture in pure form. It can be added to the tobacco and / or the wrapping material in the manner described above, it being possible for cost reasons to stretch it with up to 10% by weight of the cis isomer.
- the cis isomer remaining after working up the oxidation mixture is advantageously reduced to nicotine; the nicotine thus obtained can be oxidized again.
- the colorless solution thus obtained which is free of nicotine and hydrogen peroxide, can be processed directly.
- Example 1 The solution obtained in Example 1 is dewatered with n-propanol by azeotropic distillation. The dewatered solution is dried with molecular sieve (4A). On cooling, pure trans-nicotine N'-oxide crystallizes out of the mixture thus obtained and can be filtered off with suction. The remaining mother liquor contains predominantly cis-nicotine-N'-oxide.
- the mixture obtained has a cis / trans ratio of the nicotine N'-oxides of 1: 1.67.
- the crude product thus obtained is mixed with 25 kg of n-propanol and distilled.
- the reaction residue thus dewatered is then dried with 5 kg of molecular sieve (4A) in 5 kg of methylene chloride.
- the cis / trans ratio of the two diastereomeric nicotine N'-oxides is 1: 1.67.
- the reaction mixture is subjected to azeotropic dewatering.
- azeotropic dewatering For this purpose, 10.6 kg of n-propanol are added and a water-containing distillate (75% by mass n-propanol / 25% water) is separated off under a slight vacuum.
- the low-water residue has a residual water content of 7.7% by mass.
- Nicotinization of a cigarette strand Nicotinization of a cigarette strand.
- the tobacco nicotine content is increased with the help of a 10% alcoholic trans-nicotine N'-oxide solution by 1.13% to 2.62%; the addition is made by spraying on the tobacco material.
- the cigarettes made from the tobacco material obtained in this way have a smoke nicotine yield which is 0.3 mg higher when smoking under DIN conditions.
- the condensate content remains unchanged compared to untreated cigarettes.
- Cigarette strand nicotinization Cigarette strand nicotinization.
- a tobacco mixture with a nicotine content of 1.66% is raised to 6.1% with a 20% aqueous trans-nicotine N'-oxide solution in the leaf cut nicotine content.
- the cigarettes then made from this tobacco material result in a smoke nicotine yield increased by 0.5 mg when smoking under DIN conditions.
- the condensate content did not change compared to untreated cigarettes.
- a cigarette paper web 200 m of a cigarette paper web are moistened on the back with the aid of rollers with a 10% trans-nicotine-N'-oxide solution in water / ethanol (1: 1) and dried in a hot air stream. After drying, the cigarette paper obtained is similar in color and mechanical stability to the untreated pattern and contributes to an increase in nicotine smoke.
- the amount of the trans-nicotine N'-oxide applied in accordance with the process is 5%, based on the cigarette paper weight.
- Nicotine compensation by adding trans-nicotine N'-oxide before an expansion process 50 kg of a filler grade with a nicotine content of 1.8% by weight and a moisture content of 11% by weight are made using a trans-nicotine-N'-oxide solution consisting of 4.3 l of water and 200 g of trans-nicotine N'-oxide, brought to an expansion moisture of approx. 18% by weight.
- trans-nicotine-N'-oxide compensates for the 25% loss of nicotine which is always to be expected in tobacco expansion processes, so that the expanded tobacco with its original nicotine content can contribute to the mixture build-up.
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Tobacco Products (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (15)
1. Produit à fumer et, en particulier, tabac avec ou sans matériau d'enveloppe, contenant du N'- oxyde de nicotine, caractérisé en ce qu'il contient, en quantités pouvant atteindre 5 % en poids par rapport au poids sec du produit à fumer, du N'-oxydé de nicotine sous forme d'oxyde de nicotine-N'-trans qui est exempt ou essentiellement exempt d'oxyde de nicotine-N'- cis, ou qui présente une teneur d'isomère-cis égale au maximum à 10 % en poids.
2. Produit à fumer selon la revendication 1, caractérisé en ce que l'oxyde de nicotine-N'-trans qui est exempt ou est essentiellement exempt d'oxyde de nicotine-N'-cis, ou qui présente une teneur en isomère-cis égale à 10 % en poids au maximum, est ajouté au tabac et/ou au matériau d'enveloppe.
3. Procédé pour la production d'oxyde de nicotine-N'-trans qui est exempt ou essentiellement exempt d'oxyde de nicotine-N'-cis à utiliser dans les produits à fumer selon la revendication 1 ou 2, par oxydation de la nicotine avec des solutions aqueuses de H202, caractérisé en ce que l'on effectue l'oxydation en présence de quantités catalytiques d'acides organiques et/ou inorganiques non oxydants ayant une valeur de pKa inférieure à 5.
4. Procédé selon la revendication 3, caractérisé en ce que l'on ajoute le H202 et la nicotine en quantités essentiellement équimoléculaires.
5. Procédé selon la revendication 3 ou 4, caractérisé en ce que l'on introduit d'abord le H202 et que l'on ajoute ensuite la nicotine goutte à goutte.
6. Procédé selon la revendication 4, caractérisé en ce que l'on introduit tout d'abord la nicotine et que l'on ajoute ensuite le H202 goutte à goutte.
7. Procédé selon l'une des revendications 3 à 6, caractérisé en ce que l'on utilise le H202 sous forme d'une solution aqueuse à 30-50 %
8. Procédé selon l'une des revendications 3 à 7, caractérisé en ce que l'on ajoute le catalyseur en quantité égale à 10-150 mMole par mole de nicotine.
9. Procédé selon l'une des revendications 3 à 8, caractérisé en ce que l'on utilise comme catalyseur les acides carboxyliques, dicarboxyli- ques ou polycarboxyliques existant naturellement dans le tabac.
10. Procédé selon l'une des revendications 3 à 9, caractérisé en ce que l'on utilise comme catalyseur de l'acide citrique.
11. Procédé selon l'une des revendications 3 à 10, caractérisé en ce que l'on déshydrate le mélange d'oxydation obtenu après cette réaction.
12. Procédé selon l'une des revendications 3 à 11, caractérisé en ce que l'on déshydrate le mélange de réaction obtenu par oxydation, au moyen d'une distillation azéotropique.
13. Procédé selon l'une des revendications 3 à 12, caractérisé en ce que l'on utilise comme agent de déshydratation azéotropique le n-propanol.
14. Procédé selon l'une des revendications 3 à 13, caractérisé en ce que l'on élimine les traces d'eau du mélange de réaction séché au moyen d'un tamis moléculaire.
15. Procédé selon l'une des revendications 3 à 14, caractérisé en ce que l'on sépare l'oxyde de nicotine-N'-trans par cristallisation dans le mélange d'oxydation séché.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3344554 | 1983-12-09 | ||
| DE19833344554 DE3344554A1 (de) | 1983-12-09 | 1983-12-09 | Rauchprodukt, enthaltend nicotin-n' -oxid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0144934A2 EP0144934A2 (fr) | 1985-06-19 |
| EP0144934A3 EP0144934A3 (en) | 1986-03-19 |
| EP0144934B1 true EP0144934B1 (fr) | 1988-05-04 |
Family
ID=6216485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP84114573A Expired EP0144934B1 (fr) | 1983-12-09 | 1984-11-30 | Produit à fumer contenant de l'oxyde N' de nicotine |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4641667A (fr) |
| EP (1) | EP0144934B1 (fr) |
| AU (1) | AU3642084A (fr) |
| CA (1) | CA1249831A (fr) |
| DE (2) | DE3344554A1 (fr) |
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|---|---|---|---|---|
| US6479558B1 (en) * | 2000-04-04 | 2002-11-12 | Westinghouse Savannah River Company | Microbial processing of used rubber |
| US7810507B2 (en) * | 2006-02-10 | 2010-10-12 | R. J. Reynolds Tobacco Company | Smokeless tobacco composition |
| US8061362B2 (en) | 2007-07-23 | 2011-11-22 | R. J. Reynolds Tobacco Company | Smokeless tobacco composition |
| EP2377413B1 (fr) | 2007-07-23 | 2017-03-01 | R.J. Reynolds Tobacco Company | Composition de tabac sans fumée et procédé pour le traitement du tabac pour de tels usages |
| US7946295B2 (en) * | 2007-07-23 | 2011-05-24 | R. J. Reynolds Tobacco Company | Smokeless tobacco composition |
| US8506936B2 (en) * | 2008-11-25 | 2013-08-13 | Watson Laboratories, Inc. | Stabilized nicotine chewing gum |
| US8434496B2 (en) | 2009-06-02 | 2013-05-07 | R. J. Reynolds Tobacco Company | Thermal treatment process for tobacco materials |
| US8991403B2 (en) | 2009-06-02 | 2015-03-31 | R.J. Reynolds Tobacco Company | Thermal treatment process for tobacco materials |
| US8944072B2 (en) | 2009-06-02 | 2015-02-03 | R.J. Reynolds Tobacco Company | Thermal treatment process for tobacco materials |
| US9420825B2 (en) | 2012-02-13 | 2016-08-23 | R.J. Reynolds Tobacco Company | Whitened tobacco composition |
| US9339058B2 (en) | 2012-04-19 | 2016-05-17 | R. J. Reynolds Tobacco Company | Method for producing microcrystalline cellulose from tobacco and related tobacco product |
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-
1983
- 1983-12-09 DE DE19833344554 patent/DE3344554A1/de not_active Withdrawn
-
1984
- 1984-11-30 EP EP84114573A patent/EP0144934B1/fr not_active Expired
- 1984-11-30 DE DE8484114573T patent/DE3470830D1/de not_active Expired
- 1984-12-07 CA CA000469624A patent/CA1249831A/fr not_active Expired
- 1984-12-07 AU AU36420/84A patent/AU3642084A/en not_active Abandoned
- 1984-12-07 US US06/679,573 patent/US4641667A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU3642084A (en) | 1985-06-13 |
| DE3344554A1 (de) | 1985-06-20 |
| EP0144934A3 (en) | 1986-03-19 |
| US4641667A (en) | 1987-02-10 |
| EP0144934A2 (fr) | 1985-06-19 |
| CA1249831A (fr) | 1989-02-07 |
| DE3470830D1 (en) | 1988-06-09 |
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