CA1157867A - Continuous process for the production of dichloroacetamides - Google Patents
Continuous process for the production of dichloroacetamidesInfo
- Publication number
- CA1157867A CA1157867A CA000376175A CA376175A CA1157867A CA 1157867 A CA1157867 A CA 1157867A CA 000376175 A CA000376175 A CA 000376175A CA 376175 A CA376175 A CA 376175A CA 1157867 A CA1157867 A CA 1157867A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- dichloroacetyl
- oxazolidine
- desired product
- chloride
- 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
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical class NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 238000010924 continuous production Methods 0.000 title claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 35
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims abstract description 28
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims abstract description 14
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- RLJHUAABUCHYNU-UHFFFAOYSA-N 2,2-dichloro-1-(1,3-oxazolidin-3-yl)ethanone Chemical class ClC(Cl)C(=O)N1CCOC1 RLJHUAABUCHYNU-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 3
- 239000007788 liquid Substances 0.000 claims description 13
- 239000012074 organic phase Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000012267 brine Substances 0.000 claims description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- 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 claims description 4
- 230000004087 circulation Effects 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000010923 batch production Methods 0.000 abstract description 6
- 150000001408 amides Chemical class 0.000 abstract description 5
- 230000002844 continuous effect Effects 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 14
- 239000012071 phase Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000004009 herbicide Substances 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 229960001413 acetanilide Drugs 0.000 description 7
- -1 amine salts Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 150000001263 acyl chlorides Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000729 antidote Substances 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229940075522 antidotes Drugs 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229940080263 sodium dichloroacetate Drugs 0.000 description 2
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 2
- LUPNKHXLFSSUGS-UHFFFAOYSA-M sodium;2,2-dichloroacetate Chemical compound [Na+].[O-]C(=O)C(Cl)Cl LUPNKHXLFSSUGS-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- XMPCGZCCOXWBKR-UHFFFAOYSA-N 2,2,5-trimethyl-1,3-oxazolidine Chemical compound CC1CNC(C)(C)O1 XMPCGZCCOXWBKR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- 241000272470 Circus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 description 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 150000007982 azolidines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- BGQJNGISTPIALH-UHFFFAOYSA-N n,n-bis(prop-2-enyl)acetamide Chemical compound C=CCN(C(=O)C)CC=C BGQJNGISTPIALH-UHFFFAOYSA-N 0.000 description 1
- IMWJKBXVWDPMQF-UHFFFAOYSA-N n-(ethoxymethyl)-n-(2-ethylphenyl)acetamide Chemical compound CCOCN(C(C)=O)C1=CC=CC=C1CC IMWJKBXVWDPMQF-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material 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
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/144,500 US4278799A (en) | 1980-04-28 | 1980-04-28 | Continuous process for the production of dichloroacetamides |
| US144,500 | 1980-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1157867A true CA1157867A (en) | 1983-11-29 |
Family
ID=22508885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000376175A Expired CA1157867A (en) | 1980-04-28 | 1981-04-24 | Continuous process for the production of dichloroacetamides |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4278799A (en, 2012) |
| EP (1) | EP0039166B1 (en, 2012) |
| JP (1) | JPS56167672A (en, 2012) |
| KR (1) | KR840002443B1 (en, 2012) |
| AT (1) | ATE8875T1 (en, 2012) |
| BR (1) | BR8102388A (en, 2012) |
| CA (1) | CA1157867A (en, 2012) |
| CS (1) | CS226428B2 (en, 2012) |
| DD (1) | DD158643A5 (en, 2012) |
| DE (1) | DE3165344D1 (en, 2012) |
| DK (1) | DK158465C (en, 2012) |
| HU (1) | HU186408B (en, 2012) |
| IL (1) | IL62721A (en, 2012) |
| PL (1) | PL133589B1 (en, 2012) |
| ZA (1) | ZA812763B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990005725A1 (en) * | 1988-11-14 | 1990-05-31 | Ici Americas Inc. | Process for the acylation of thiazolidines |
| JPH0376060A (ja) * | 1989-08-16 | 1991-04-02 | Nec Corp | 磁気ディスク装置のヘッド位置決め装置 |
| WO1991012229A1 (en) * | 1990-02-12 | 1991-08-22 | National Research Council Of Canada | Process for preparing acyl derivatives of acylatable compounds |
| CN114213271A (zh) * | 2021-12-30 | 2022-03-22 | 徐州彰梁生化科技有限公司 | 一种二氯丙烯胺的制备方法 |
| CN117247328B (zh) * | 2023-09-13 | 2025-04-22 | 无锡颐景丰科技有限公司 | 一种二氯丙烯胺的合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3268324A (en) * | 1965-10-11 | 1966-08-23 | Monsanto Co | Herbicidal composition and method employing oxa aliphatic acetamide |
| US3647876A (en) * | 1969-08-14 | 1972-03-07 | Virginia Chemicals Inc | Process in the preparation of n n-di-n-propyl-alpha-chloroacetamid |
| US3884671A (en) * | 1972-08-15 | 1975-05-20 | Scm Corp | Herbicidal n-haloacyl (2-alkylated) oxazolidines |
| US4186130A (en) * | 1973-05-02 | 1980-01-29 | Stauffer Chemical Company | N-(haloalkanoyl) oxazolidines |
| US3914302A (en) * | 1974-01-31 | 1975-10-21 | Stauffer Chemical Co | Process for the production of N,N-diallyldichloroacetamide |
| US3959304A (en) * | 1974-07-01 | 1976-05-25 | Stauffer Chemical Company | Certain 3-haloacyl-2,2,5-trimethyl-oxazolidines |
| US4072688A (en) * | 1975-02-14 | 1978-02-07 | Stauffer Chemical Company | Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines-herbicidal antidotes |
| US4038284A (en) * | 1975-07-28 | 1977-07-26 | Stauffer Chemical Company | N-acylation of oxazolidines |
| GB1538318A (en) * | 1976-08-09 | 1979-01-17 | Stauffer Chemical Co | Preparation of n-substituted oxazolidines |
-
1980
- 1980-04-28 US US06/144,500 patent/US4278799A/en not_active Expired - Lifetime
-
1981
- 1981-04-13 AT AT81301619T patent/ATE8875T1/de active
- 1981-04-13 EP EP81301619A patent/EP0039166B1/en not_active Expired
- 1981-04-13 DE DE8181301619T patent/DE3165344D1/de not_active Expired
- 1981-04-20 BR BR8102388A patent/BR8102388A/pt not_active IP Right Cessation
- 1981-04-24 JP JP6153781A patent/JPS56167672A/ja active Granted
- 1981-04-24 CA CA000376175A patent/CA1157867A/en not_active Expired
- 1981-04-27 IL IL62721A patent/IL62721A/xx not_active IP Right Cessation
- 1981-04-27 KR KR1019810001442A patent/KR840002443B1/ko not_active Expired
- 1981-04-27 HU HU811086A patent/HU186408B/hu not_active IP Right Cessation
- 1981-04-27 DK DK186381A patent/DK158465C/da not_active IP Right Cessation
- 1981-04-27 ZA ZA00812763A patent/ZA812763B/xx unknown
- 1981-04-27 DD DDAPC07D/2295311A patent/DD158643A5/de not_active IP Right Cessation
- 1981-04-28 CS CS813167A patent/CS226428B2/cs unknown
- 1981-04-28 PL PL1981230885A patent/PL133589B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL133589B1 (en) | 1985-06-29 |
| DE3165344D1 (en) | 1984-09-13 |
| PL230885A1 (en, 2012) | 1981-12-23 |
| DK158465B (da) | 1990-05-21 |
| JPS6412265B2 (en, 2012) | 1989-02-28 |
| DD158643A5 (de) | 1983-01-26 |
| HU186408B (en) | 1985-07-29 |
| DK158465C (da) | 1990-10-08 |
| EP0039166A1 (en) | 1981-11-04 |
| ATE8875T1 (de) | 1984-08-15 |
| DK186381A (da) | 1981-10-29 |
| IL62721A0 (en) | 1981-06-29 |
| IL62721A (en) | 1984-05-31 |
| US4278799A (en) | 1981-07-14 |
| CS226428B2 (en) | 1984-03-19 |
| ZA812763B (en) | 1982-06-30 |
| BR8102388A (pt) | 1981-12-22 |
| KR840002443B1 (ko) | 1984-12-28 |
| JPS56167672A (en) | 1981-12-23 |
| EP0039166B1 (en) | 1984-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |