CS241090B2 - Method of n-arylhalogenpyrrolidones preparation - Google Patents
Method of n-arylhalogenpyrrolidones preparation Download PDFInfo
- Publication number
- CS241090B2 CS241090B2 CS844462A CS446284A CS241090B2 CS 241090 B2 CS241090 B2 CS 241090B2 CS 844462 A CS844462 A CS 844462A CS 446284 A CS446284 A CS 446284A CS 241090 B2 CS241090 B2 CS 241090B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- amine
- hydrogen
- reaction
- copper
- chlorine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052802 copper Inorganic materials 0.000 claims abstract description 12
- 239000010949 copper Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- -1 chloro, bromo, fluoro, iodo Chemical group 0.000 claims description 7
- 150000003335 secondary amines Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical group CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 6
- 150000003141 primary amines Chemical class 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Chemical group 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- KQTOYEUYHXUEDB-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanamide Chemical compound NC(=O)C(F)(F)C(F)(F)F KQTOYEUYHXUEDB-UHFFFAOYSA-N 0.000 claims 1
- 230000009194 climbing Effects 0.000 claims 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical group CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000005619 secondary aliphatic amines Chemical class 0.000 abstract description 3
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 15
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 14
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 11
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 8
- 239000011269 tar Substances 0.000 description 8
- 150000002431 hydrogen Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229940045803 cuprous chloride Drugs 0.000 description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 6
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 5
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229960001413 acetanilide Drugs 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical group FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical group NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000003940 butylamines Chemical class 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006308 propyl amino group Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Saccharide Compounds (AREA)
- Pyridine Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Cephalosporin Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
- Fishing Rods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50513583A | 1983-06-16 | 1983-06-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS446284A2 CS446284A2 (en) | 1985-06-13 |
| CS241090B2 true CS241090B2 (en) | 1986-03-13 |
Family
ID=24009165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS844462A CS241090B2 (en) | 1983-06-16 | 1984-06-13 | Method of n-arylhalogenpyrrolidones preparation |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0129296B1 (pt) |
| JP (1) | JPS6011464A (pt) |
| KR (1) | KR890004126B1 (pt) |
| AT (1) | ATE32062T1 (pt) |
| AU (1) | AU563172B2 (pt) |
| BG (1) | BG49382A3 (pt) |
| BR (1) | BR8402873A (pt) |
| CA (1) | CA1216298A (pt) |
| CS (1) | CS241090B2 (pt) |
| DD (1) | DD224317A5 (pt) |
| DE (1) | DE3468864D1 (pt) |
| DK (1) | DK162087C (pt) |
| DZ (1) | DZ648A1 (pt) |
| EG (1) | EG20053A (pt) |
| ES (1) | ES8506618A1 (pt) |
| HU (1) | HU192034B (pt) |
| IL (1) | IL72110A (pt) |
| MA (1) | MA20147A1 (pt) |
| MX (1) | MX156039A (pt) |
| NZ (1) | NZ208537A (pt) |
| PL (1) | PL142334B1 (pt) |
| PT (1) | PT78747B (pt) |
| RO (1) | RO88419A (pt) |
| SU (1) | SU1452479A3 (pt) |
| TR (1) | TR22866A (pt) |
| YU (1) | YU44565B (pt) |
| ZA (1) | ZA844532B (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2728937B2 (ja) * | 1989-06-14 | 1998-03-18 | 三井東圧化学株式会社 | １―（３―置換ベンジル）―３―ハロゲノ―４―（１―ハロゲノアルキル）―２―ピロリジノン誘導体およびこれらを有効成分とする除草剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU179058B (en) * | 1975-03-28 | 1982-08-28 | Stauffer Chemical Co | Herbicide compositions containing n-substituted 2-pyrrolidinone derivatives and process for preparing the active substances thereof |
| US4132713A (en) * | 1977-12-23 | 1979-01-02 | Stauffer Chemical Company | Process for the preparation of N-substituted halopyrrolidones |
| DE3168705D1 (en) * | 1980-12-19 | 1985-03-14 | Ciba Geigy Ag | Fluoropyrrolidinones, process for their preparation, herbicides containing them and their use |
-
1984
- 1984-05-29 DK DK265184A patent/DK162087C/da not_active IP Right Cessation
- 1984-06-11 YU YU1021/84A patent/YU44565B/xx unknown
- 1984-06-11 RO RO84114824A patent/RO88419A/ro unknown
- 1984-06-13 TR TR4175/84A patent/TR22866A/xx unknown
- 1984-06-13 BG BG065842A patent/BG49382A3/xx unknown
- 1984-06-13 BR BR8402873A patent/BR8402873A/pt not_active IP Right Cessation
- 1984-06-13 EG EG635584A patent/EG20053A/xx active
- 1984-06-13 DZ DZ847198A patent/DZ648A1/fr active
- 1984-06-13 CS CS844462A patent/CS241090B2/cs unknown
- 1984-06-14 IL IL72110A patent/IL72110A/xx unknown
- 1984-06-14 PL PL1984248201A patent/PL142334B1/pl unknown
- 1984-06-14 DE DE8484200860T patent/DE3468864D1/de not_active Expired
- 1984-06-14 EP EP84200860A patent/EP0129296B1/en not_active Expired
- 1984-06-14 AT AT84200860T patent/ATE32062T1/de not_active IP Right Cessation
- 1984-06-15 ZA ZA844532A patent/ZA844532B/xx unknown
- 1984-06-15 CA CA000456705A patent/CA1216298A/en not_active Expired
- 1984-06-15 PT PT78747A patent/PT78747B/pt unknown
- 1984-06-15 KR KR1019840003367A patent/KR890004126B1/ko not_active Expired
- 1984-06-15 NZ NZ208537A patent/NZ208537A/en unknown
- 1984-06-15 HU HU842318A patent/HU192034B/hu not_active IP Right Cessation
- 1984-06-15 SU SU3753761A patent/SU1452479A3/ru active
- 1984-06-15 ES ES533471A patent/ES8506618A1/es not_active Expired
- 1984-06-15 AU AU29429/84A patent/AU563172B2/en not_active Ceased
- 1984-06-15 MX MX201673A patent/MX156039A/es unknown
- 1984-06-15 DD DD84264189A patent/DD224317A5/de not_active IP Right Cessation
- 1984-06-16 JP JP59122964A patent/JPS6011464A/ja active Granted
- 1984-06-21 MA MA20371A patent/MA20147A1/fr unknown
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