JPS584028B2 - ２− ビニルオキサゾリンノ セイゾウホウホウ - Google Patents
２− ビニルオキサゾリンノ セイゾウホウホウInfo
- Publication number
- JPS584028B2 JPS584028B2 JP49064160A JP6416074A JPS584028B2 JP S584028 B2 JPS584028 B2 JP S584028B2 JP 49064160 A JP49064160 A JP 49064160A JP 6416074 A JP6416074 A JP 6416074A JP S584028 B2 JPS584028 B2 JP S584028B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- formula
- general formula
- torr
- cyclobutane
- 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
- BQBSIHIZDSHADD-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1,3-oxazole Chemical compound C=CC1=NCCO1 BQBSIHIZDSHADD-UHFFFAOYSA-N 0.000 title claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- CZPLUOCTUPJSIZ-UHFFFAOYSA-N cyclobutane-1,2-dicarbonitrile Chemical compound N#CC1CCC1C#N CZPLUOCTUPJSIZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- NZJCVMHRSVZYDC-UHFFFAOYSA-N 2-[2-(4,5-dihydro-1,3-oxazol-2-yl)cyclobutyl]-4,5-dihydro-1,3-oxazole Chemical compound C1CC(C=2OCCN=2)C1C1=NCCO1 NZJCVMHRSVZYDC-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- -1 Oxazolin-2-ylbutanenitrile Chemical compound 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 239000007858 starting material Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 150000002918 oxazolines Chemical class 0.000 description 3
- PJZWQIIERANBOC-UHFFFAOYSA-N (2-ethenyl-4-methyl-5h-1,3-oxazol-4-yl)methanol Chemical compound OCC1(C)COC(C=C)=N1 PJZWQIIERANBOC-UHFFFAOYSA-N 0.000 description 2
- UNFQMQYNYXLTPF-UHFFFAOYSA-N 1-(4,5-dihydro-1,3-oxazol-2-yl)cyclobutane-1-carbonitrile Chemical compound N=1CCOC=1C1(C#N)CCC1 UNFQMQYNYXLTPF-UHFFFAOYSA-N 0.000 description 2
- HMEVYZZCEGUONQ-UHFFFAOYSA-N 2-ethenyl-5-methyl-4,5-dihydro-1,3-oxazole Chemical compound CC1CN=C(C=C)O1 HMEVYZZCEGUONQ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CZPLUOCTUPJSIZ-WDSKDSINSA-N (1r,2r)-cyclobutane-1,2-dicarbonitrile Chemical compound N#C[C@@H]1CC[C@H]1C#N CZPLUOCTUPJSIZ-WDSKDSINSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- PAWVJRPRVYDHLQ-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)ethanol Chemical compound OCCC1=NCCO1 PAWVJRPRVYDHLQ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- SDEXZERWEBDHSL-UHFFFAOYSA-N 2-ethenyl-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=C)=N1 SDEXZERWEBDHSL-UHFFFAOYSA-N 0.000 description 1
- PBYIFPWEHGSUEY-UHFFFAOYSA-N 2-ethenyl-4-methyl-4,5-dihydro-1,3-oxazole Chemical compound CC1COC(C=C)=N1 PBYIFPWEHGSUEY-UHFFFAOYSA-N 0.000 description 1
- YOJUVVCZNBLEFL-UHFFFAOYSA-N 2-ethenyl-5-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1C(C=C)=NCC1C1=CC=CC=C1 YOJUVVCZNBLEFL-UHFFFAOYSA-N 0.000 description 1
- GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- SVMILKYZKYTPNM-UHFFFAOYSA-N 5-methyl-2-[2-(5-methyl-4,5-dihydro-1,3-oxazol-2-yl)cyclobutyl]-4,5-dihydro-1,3-oxazole Chemical compound O1C(C)CN=C1C1C(C=2OC(C)CN=2)CC1 SVMILKYZKYTPNM-UHFFFAOYSA-N 0.000 description 1
- CIIILUMBZOGKDF-UHFFFAOYSA-N 5-methyl-4,5-dihydro-1,3-oxazole Chemical compound CC1CN=CO1 CIIILUMBZOGKDF-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WKHGMYYFOWRTOU-UHFFFAOYSA-N [2-[2-[4-(hydroxymethyl)-4-methyl-5h-1,3-oxazol-2-yl]cyclobutyl]-4-methyl-5h-1,3-oxazol-4-yl]methanol Chemical compound OCC1(C)COC(C2C(CC2)C=2OCC(C)(CO)N=2)=N1 WKHGMYYFOWRTOU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- LHQLJMJLROMYRN-UHFFFAOYSA-L cadmium acetate Chemical compound [Cd+2].CC([O-])=O.CC([O-])=O LHQLJMJLROMYRN-UHFFFAOYSA-L 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2329545A DE2329545C2 (de) | 1973-06-09 | 1973-06-09 | 1,2-Bis-oxazolinyl-(2)-cyclobutane und Verfahren zu ihrer Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5032173A JPS5032173A (enExample) | 1975-03-28 |
| JPS584028B2 true JPS584028B2 (ja) | 1983-01-24 |
Family
ID=5883583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49064160A Expired JPS584028B2 (ja) | 1973-06-09 | 1974-06-07 | ２− ビニルオキサゾリンノ セイゾウホウホウ |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3962270A (enExample) |
| JP (1) | JPS584028B2 (enExample) |
| BE (1) | BE816033A (enExample) |
| CH (1) | CH599186A5 (enExample) |
| DE (1) | DE2329545C2 (enExample) |
| DK (1) | DK307074A (enExample) |
| FR (1) | FR2232547B1 (enExample) |
| GB (1) | GB1478026A (enExample) |
| IE (1) | IE39304B1 (enExample) |
| IT (1) | IT1013404B (enExample) |
| LU (1) | LU70264A1 (enExample) |
| NL (1) | NL7407610A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1056842A (en) * | 1975-06-12 | 1979-06-19 | Masayuki Narisada | Dihydroethanoanthracene derivatives |
| GB1518280A (en) * | 1976-09-15 | 1978-07-19 | Texaco Development Corp | Method of preparing alpha-vinyloxazolines |
| US4543414A (en) * | 1978-12-05 | 1985-09-24 | The Dow Chemical Company | Liquid phase preparation of 2-substituted-2-oxazolines with cadmium salt catalysts |
| US4334075A (en) * | 1980-09-22 | 1982-06-08 | E. I. Du Pont De Nemours And Company | Oxazoline diesters |
| EP0401286B1 (en) * | 1988-02-25 | 1995-09-13 | The Dow Chemical Company | Process for preparing n-(hydroxyalkyl)-2-unsaturated amides and 2-alkenyl oxazolines |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1067437B (de) * | 1956-05-11 | 1959-10-22 | Rohm & Haas Company, Philadelphia, Pa. (V. St. A.) | Verfahren zur Herstellung von 4,4-dialkyl-2vinyl- und 4,4-dialkyl-2-isopropenylsu'bstituierten Oxazolinen und 5,6-Dihydro-4H!-1,3-oχ3zinen sowie deren Spiranen |
| US3505297A (en) * | 1963-01-21 | 1970-04-07 | Dow Chemical Co | Alkenyl heterocycles and their polymers |
| US3637689A (en) * | 1969-05-31 | 1972-01-25 | Asahi Chemical Ind | Process for the preparation of 4 6-diamino-2-vinyl-s-triazine |
| US3678065A (en) * | 1970-12-09 | 1972-07-18 | Commercial Solvents Corp | Production of hydroxymethyl vinyl oxazoline |
| DE2127776A1 (de) * | 1971-06-04 | 1972-12-14 | Chemische Werke Hüls AG, 4370 Mari | Verfahren zur Herstellung cyclischer Imidsäureester |
-
1973
- 1973-06-09 DE DE2329545A patent/DE2329545C2/de not_active Expired
-
1974
- 1974-05-21 US US05/472,016 patent/US3962270A/en not_active Expired - Lifetime
- 1974-06-06 NL NL7407610A patent/NL7407610A/xx not_active Application Discontinuation
- 1974-06-07 GB GB2532574A patent/GB1478026A/en not_active Expired
- 1974-06-07 IT IT51436/74A patent/IT1013404B/it active
- 1974-06-07 JP JP49064160A patent/JPS584028B2/ja not_active Expired
- 1974-06-07 IE IE1197/74A patent/IE39304B1/xx unknown
- 1974-06-07 CH CH784274A patent/CH599186A5/xx not_active IP Right Cessation
- 1974-06-07 FR FR7419787A patent/FR2232547B1/fr not_active Expired
- 1974-06-07 DK DK307074A patent/DK307074A/da unknown
- 1974-06-07 LU LU70264A patent/LU70264A1/xx unknown
- 1974-06-07 BE BE145168A patent/BE816033A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK307074A (enExample) | 1975-02-03 |
| BE816033A (fr) | 1974-12-09 |
| US3962270A (en) | 1976-06-08 |
| IE39304B1 (en) | 1978-09-13 |
| FR2232547B1 (enExample) | 1978-01-13 |
| JPS5032173A (enExample) | 1975-03-28 |
| GB1478026A (en) | 1977-06-29 |
| IT1013404B (it) | 1977-03-30 |
| LU70264A1 (enExample) | 1975-03-06 |
| FR2232547A1 (enExample) | 1975-01-03 |
| NL7407610A (enExample) | 1974-12-11 |
| DE2329545A1 (de) | 1975-01-02 |
| IE39304L (en) | 1974-12-09 |
| DE2329545C2 (de) | 1986-06-12 |
| CH599186A5 (enExample) | 1978-05-12 |
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