CA1067098A - Synthetic musk perfume compound 1,1,2,3,3,5- hexamethylindan-6-nitrile - Google Patents
Synthetic musk perfume compound 1,1,2,3,3,5- hexamethylindan-6-nitrileInfo
- Publication number
- CA1067098A CA1067098A CA269,879A CA269879A CA1067098A CA 1067098 A CA1067098 A CA 1067098A CA 269879 A CA269879 A CA 269879A CA 1067098 A CA1067098 A CA 1067098A
- Authority
- CA
- Canada
- Prior art keywords
- nitrile
- compound
- hexamethylindan
- odor
- musk
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 31
- IFBLMNBANYFBBN-UHFFFAOYSA-N 1,1,2,3,3,6-hexamethyl-2h-indene-5-carbonitrile Chemical compound CC1=C(C#N)C=C2C(C)(C)C(C)C(C)(C)C2=C1 IFBLMNBANYFBBN-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000002304 perfume Substances 0.000 title claims description 11
- 241000402754 Erythranthe moschata Species 0.000 title abstract description 28
- 239000000203 mixture Substances 0.000 claims description 6
- 239000004615 ingredient Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 abstract description 7
- 235000019645 odor Nutrition 0.000 description 24
- 239000000243 solution Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 150000002825 nitriles Chemical class 0.000 description 13
- 230000000875 corresponding effect Effects 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001816 cooling Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- VDBHOHJWUDKDRW-UHFFFAOYSA-N 1-(1,1,2,3,3,6-hexamethyl-2h-inden-5-yl)ethanone Chemical compound CC1=C(C(C)=O)C=C2C(C)(C)C(C)C(C)(C)C2=C1 VDBHOHJWUDKDRW-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 colognes Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- KSEZPRJUTHMFGZ-UHFFFAOYSA-N 1-(3-ethyl-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCC(C)(C)C2=C1C=C(C(C)=O)C(CC)=C2 KSEZPRJUTHMFGZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000207840 Jasminum Species 0.000 description 2
- 235000010254 Jasminum officinale Nutrition 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SKSSEPUCENPDJA-UHFFFAOYSA-N 1,1,2,3,3,6-hexamethyl-2h-indene-5-carboxamide Chemical compound CC1=C(C(N)=O)C=C2C(C)(C)C(C)C(C)(C)C2=C1 SKSSEPUCENPDJA-UHFFFAOYSA-N 0.000 description 1
- FSMFLKCQIQYWKU-UHFFFAOYSA-N 1,1,2,3,3,6-hexamethyl-2h-indene-5-carboxylic acid Chemical compound CC1=C(C(O)=O)C=C2C(C)(C)C(C)C(C)(C)C2=C1 FSMFLKCQIQYWKU-UHFFFAOYSA-N 0.000 description 1
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 1
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 description 1
- LELXPNKVSBCRLR-UHFFFAOYSA-N 3-ethyl-5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonitrile Chemical compound CC1(C)CCC(C)(C)C2=C1C=C(C#N)C(CC)=C2 LELXPNKVSBCRLR-UHFFFAOYSA-N 0.000 description 1
- WXCMHFPAUCOJIG-UHFFFAOYSA-N 4'-tert-Butyl-2',6'-dimethyl-3',5'-dinitroacetophenone Chemical compound CC(=O)C1=C(C)C([N+]([O-])=O)=C(C(C)(C)C)C([N+]([O-])=O)=C1C WXCMHFPAUCOJIG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 241000509579 Draco Species 0.000 description 1
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
- 241000282375 Herpestidae Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940043379 ammonium hydroxide Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000001666 citrus aurantium l. flower Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000001524 citrus aurantium oil Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940093468 ethylene brassylate Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/678,782 US4018719A (en) | 1976-04-20 | 1976-04-20 | Synthetic musk perfume compound 1,1,2,3,3,5-hexamethylindan-6-nitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067098A true CA1067098A (en) | 1979-11-27 |
Family
ID=24724241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA269,879A Expired CA1067098A (en) | 1976-04-20 | 1977-01-17 | Synthetic musk perfume compound 1,1,2,3,3,5- hexamethylindan-6-nitrile |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4018719A (https=) |
| JP (1) | JPS6059225B2 (https=) |
| AU (1) | AU511919B2 (https=) |
| BE (1) | BE849824A (https=) |
| CA (1) | CA1067098A (https=) |
| CH (1) | CH618344A5 (https=) |
| DE (1) | DE2716537C2 (https=) |
| FR (1) | FR2348916A1 (https=) |
| GB (1) | GB1530433A (https=) |
| IL (1) | IL51908A (https=) |
| IT (1) | IT1078414B (https=) |
| NL (1) | NL188525C (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289661A (en) * | 1978-10-20 | 1981-09-15 | International Flavors & Fragrances Inc. | Acetyl hydrindacenes, acetyl indanes, mixtures of same, processes for preparing same and organoleptic uses thereof |
| EP0164763B1 (de) * | 1979-08-10 | 1987-06-16 | L. Givaudan & Cie Société Anonyme | Neue substituierte Tetraline und Indane (I), Verwendung von (I) als Riech- und/oder Geschmackstoffe sowie Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an (I) |
| US4483786A (en) * | 1983-05-27 | 1984-11-20 | Fritzsche Dodge & Olcott Inc. | Nitrile musk composition |
| EP0379981B1 (de) * | 1989-01-27 | 1993-04-07 | L. GIVAUDAN & CIE Société Anonyme | Acetale von Oxo-tetralinen und von Oxo-indanen |
| ES2060218T3 (es) * | 1990-03-02 | 1994-11-16 | Givaudan Roure Int | Cetona biciclica polisubstituida. |
| US5206217A (en) * | 1990-11-21 | 1993-04-27 | Union Camp Corporation | Indane compounds and compositions |
| US5321173A (en) * | 1990-11-21 | 1994-06-14 | Union Camp Corporation | Indane compounds and compositions |
| EP0618897B1 (en) * | 1991-12-20 | 1997-09-17 | Union Camp Corporation | Nitrile and aldoxime indane compounds, their use as perfume |
| US5204322A (en) * | 1991-12-31 | 1993-04-20 | Union Camp Corporation | Nitrile and aldoxime indane compounds and compositions |
| US5403823A (en) * | 1993-06-18 | 1995-04-04 | Union Camp Corporation | Alkyl indane aldehyde compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2889367A (en) * | 1959-06-02 | dimethyl-g t-isutyl indanes | ||
| US2507473A (en) * | 1946-01-03 | 1950-05-09 | Smith Kline French Lab | Coumaran derivatives and process for preparing same |
| US2759022A (en) * | 1951-08-27 | 1956-08-14 | Polak Frutal Works | Musk odorant |
| US2897237A (en) * | 1953-12-14 | 1959-07-28 | Givaudan Corp | Substituted tetrahydronaphthalenes |
| US3644540A (en) * | 1967-10-10 | 1972-02-22 | Givaudan Corp | 5 7 - diisopropyl-1 1-dimethyl-6-hydroxyindan and process for preparing same |
| US3920585A (en) * | 1972-03-06 | 1975-11-18 | Dragoco Gerberding Co Gmbh | Perfume composition including isomeric mixture of bicyclic nitriles |
| US3910853A (en) * | 1974-07-29 | 1975-10-07 | Fritzsche Dodge & Olcott Inc | 1,1,4,4-Tetra methyl-alkyl-nitriles-tetrahydronaphthalene perfume compositions |
-
1976
- 1976-04-20 US US05/678,782 patent/US4018719A/en not_active Expired - Lifetime
- 1976-12-21 FR FR7638469A patent/FR2348916A1/fr not_active Withdrawn
- 1976-12-23 BE BE173611A patent/BE849824A/xx not_active IP Right Cessation
- 1976-12-23 CH CH1624276A patent/CH618344A5/fr not_active IP Right Cessation
-
1977
- 1977-01-11 JP JP52001859A patent/JPS6059225B2/ja not_active Expired
- 1977-01-17 CA CA269,879A patent/CA1067098A/en not_active Expired
- 1977-02-09 GB GB5306/77A patent/GB1530433A/en not_active Expired
- 1977-04-14 DE DE2716537A patent/DE2716537C2/de not_active Expired
- 1977-04-19 AU AU24422/77A patent/AU511919B2/en not_active Expired
- 1977-04-19 NL NLAANVRAGE7704254,A patent/NL188525C/xx not_active IP Right Cessation
- 1977-04-19 IT IT22616/77A patent/IT1078414B/it active
- 1977-04-19 IL IL51908A patent/IL51908A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1078414B (it) | 1985-05-08 |
| DE2716537C2 (de) | 1985-10-03 |
| IL51908A0 (en) | 1977-06-30 |
| JPS52128360A (en) | 1977-10-27 |
| NL7704254A (nl) | 1977-10-24 |
| AU2442277A (en) | 1978-10-26 |
| DE2716537A1 (de) | 1977-11-03 |
| AU511919B2 (en) | 1980-09-11 |
| FR2348916A1 (fr) | 1977-11-18 |
| JPS6059225B2 (ja) | 1985-12-24 |
| GB1530433A (en) | 1978-11-01 |
| US4018719A (en) | 1977-04-19 |
| IL51908A (en) | 1980-10-26 |
| BE849824A (fr) | 1977-06-23 |
| CH618344A5 (https=) | 1980-07-31 |
| NL188525C (nl) | 1992-07-16 |
| NL188525B (nl) | 1992-02-17 |
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