LU82122A1 - Procede de stabilisation d'agents d'halogenation phosphitede triaryle/halogene - Google Patents
Procede de stabilisation d'agents d'halogenation phosphitede triaryle/halogene Download PDFInfo
- Publication number
- LU82122A1 LU82122A1 LU82122A LU82122A LU82122A1 LU 82122 A1 LU82122 A1 LU 82122A1 LU 82122 A LU82122 A LU 82122A LU 82122 A LU82122 A LU 82122A LU 82122 A1 LU82122 A1 LU 82122A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- kinetic
- bromine
- chlorine
- tertiary amine
- strong
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 229910052736 halogen Inorganic materials 0.000 title description 18
- 150000002367 halogens Chemical class 0.000 title description 18
- 230000002140 halogenating effect Effects 0.000 title description 10
- 230000006641 stabilisation Effects 0.000 title description 9
- 238000011105 stabilization Methods 0.000 title description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 34
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052794 bromium Chemical group 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 150000003512 tertiary amines Chemical class 0.000 claims description 23
- 239000003960 organic solvent Substances 0.000 claims description 22
- 238000005658 halogenation reaction Methods 0.000 claims description 20
- 230000026030 halogenation Effects 0.000 claims description 17
- 239000008139 complexing agent Substances 0.000 claims description 16
- 230000000087 stabilizing effect Effects 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- 238000005481 NMR spectroscopy Methods 0.000 claims description 10
- 239000003381 stabilizer Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 229910001507 metal halide Inorganic materials 0.000 claims description 3
- 150000005309 metal halides Chemical class 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
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- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 230000009102 absorption Effects 0.000 claims 1
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- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
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- 239000000047 product Substances 0.000 description 65
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- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
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- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 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
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- PPHQUIPUBYPZLD-UHFFFAOYSA-N n-ethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1 PPHQUIPUBYPZLD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 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
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- KXDRRFQARLPIBW-UHFFFAOYSA-N tris(2-chlorophenyl) phosphite Chemical compound ClC1=CC=CC=C1OP(OC=1C(=CC=CC=1)Cl)OC1=CC=CC=C1Cl KXDRRFQARLPIBW-UHFFFAOYSA-N 0.000 description 1
- AZLGDNBTDKZORI-UHFFFAOYSA-N tris(3-methylphenyl) phosphite Chemical compound CC1=CC=CC(OP(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 AZLGDNBTDKZORI-UHFFFAOYSA-N 0.000 description 1
- WODHAGGSETVBML-UHFFFAOYSA-N tris(4-butylphenyl) phosphite Chemical compound C1=CC(CCCC)=CC=C1OP(OC=1C=CC(CCCC)=CC=1)OC1=CC=C(CCCC)C=C1 WODHAGGSETVBML-UHFFFAOYSA-N 0.000 description 1
- DFQHFXCKNSCDFW-UHFFFAOYSA-N tris(4-chlorophenyl) phosphate Chemical compound C1=CC(Cl)=CC=C1OP(=O)(OC=1C=CC(Cl)=CC=1)OC1=CC=C(Cl)C=C1 DFQHFXCKNSCDFW-UHFFFAOYSA-N 0.000 description 1
- VDAQOERDAAOXQV-UHFFFAOYSA-N tris(4-methoxyphenyl) phosphite Chemical compound C1=CC(OC)=CC=C1OP(OC=1C=CC(OC)=CC=1)OC1=CC=C(OC)C=C1 VDAQOERDAAOXQV-UHFFFAOYSA-N 0.000 description 1
- ONPCEUYAHKMPDV-UHFFFAOYSA-N tris(4-propan-2-yloxyphenyl) phosphite Chemical compound C1=CC(OC(C)C)=CC=C1OP(OC=1C=CC(OC(C)C)=CC=1)OC1=CC=C(OC(C)C)C=C1 ONPCEUYAHKMPDV-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/146—Esters of phosphorous acids containing P-halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/025—Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/008,648 US4240988A (en) | 1979-02-01 | 1979-02-01 | Method of stabilization of kinetically controlled triaryl phosphite-halogen compounds |
| US864879 | 1979-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82122A1 true LU82122A1 (fr) | 1980-04-23 |
Family
ID=21732847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82122A LU82122A1 (fr) | 1979-02-01 | 1980-01-31 | Procede de stabilisation d'agents d'halogenation phosphitede triaryle/halogene |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US4240988A (pt) |
| EP (1) | EP0015080B1 (pt) |
| JP (1) | JPS55104290A (pt) |
| KR (1) | KR840000281B1 (pt) |
| AT (1) | AT376686B (pt) |
| AU (1) | AU533041B2 (pt) |
| BE (1) | BE881427A (pt) |
| BG (1) | BG34759A3 (pt) |
| CA (1) | CA1132597A (pt) |
| CH (1) | CH643856A5 (pt) |
| CS (1) | CS214695B2 (pt) |
| DD (1) | DD151171A5 (pt) |
| DE (1) | DE3064068D1 (pt) |
| DK (1) | DK146130C (pt) |
| EG (1) | EG14942A (pt) |
| ES (1) | ES488235A0 (pt) |
| FI (1) | FI67085C (pt) |
| FR (1) | FR2447929A1 (pt) |
| GB (1) | GB2041939B (pt) |
| GR (1) | GR71612B (pt) |
| IE (1) | IE49504B1 (pt) |
| IL (1) | IL59268A (pt) |
| IT (1) | IT1130241B (pt) |
| LU (1) | LU82122A1 (pt) |
| MA (1) | MA18716A1 (pt) |
| MW (1) | MW780A1 (pt) |
| MX (1) | MX6641E (pt) |
| NL (1) | NL192110C (pt) |
| NO (1) | NO159726C (pt) |
| NZ (1) | NZ192748A (pt) |
| OA (1) | OA06452A (pt) |
| PH (1) | PH16214A (pt) |
| PL (1) | PL120815B1 (pt) |
| PT (1) | PT70745A (pt) |
| RO (1) | RO79330A (pt) |
| SU (1) | SU999976A3 (pt) |
| YU (1) | YU22380A (pt) |
| ZA (1) | ZA80524B (pt) |
| ZM (1) | ZM1380A1 (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0526551U (ja) * | 1991-09-26 | 1993-04-06 | 西川化成株式会社 | 車輌用内装パネルの位置決めピン |
| US5604222A (en) * | 1993-12-27 | 1997-02-18 | Lupin Laboratories, Ltd. | Method for the preparation of 2-chloro sulfinyl azetidinones |
| US5578721A (en) * | 1994-07-11 | 1996-11-26 | Lupin Laboratories Limited | Process for preparation of 3-exomethylene cepham sulfoxide esters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2114866A (en) * | 1936-02-08 | 1938-04-19 | Carbide & Carbon Chem Corp | Purification of esters of inorganic acids |
| US3553298A (en) * | 1967-10-20 | 1971-01-05 | Hooker Chemical Corp | Hydrolytic stabilized phosphite esters |
-
1979
- 1979-02-01 US US06/008,648 patent/US4240988A/en not_active Expired - Lifetime
-
1980
- 1980-01-29 AU AU55028/80A patent/AU533041B2/en not_active Expired
- 1980-01-29 ZA ZA00800524A patent/ZA80524B/xx unknown
- 1980-01-29 GR GR61065A patent/GR71612B/el unknown
- 1980-01-29 YU YU00223/80A patent/YU22380A/xx unknown
- 1980-01-29 PT PT70745A patent/PT70745A/pt active IP Right Revival
- 1980-01-29 IL IL59268A patent/IL59268A/xx unknown
- 1980-01-29 NZ NZ192748A patent/NZ192748A/xx unknown
- 1980-01-29 NL NL8000543A patent/NL192110C/nl not_active IP Right Cessation
- 1980-01-29 EG EG55/80A patent/EG14942A/xx active
- 1980-01-29 MA MA18913A patent/MA18716A1/fr unknown
- 1980-01-30 BE BE1/9703A patent/BE881427A/fr not_active IP Right Cessation
- 1980-01-30 FR FR8001970A patent/FR2447929A1/fr active Granted
- 1980-01-30 CA CA344,680A patent/CA1132597A/en not_active Expired
- 1980-01-30 BG BG8046411A patent/BG34759A3/xx unknown
- 1980-01-31 DE DE8080300285T patent/DE3064068D1/de not_active Expired
- 1980-01-31 JP JP1196480A patent/JPS55104290A/ja active Granted
- 1980-01-31 GB GB8003291A patent/GB2041939B/en not_active Expired
- 1980-01-31 IT IT19611/80A patent/IT1130241B/it active
- 1980-01-31 NO NO800249A patent/NO159726C/no unknown
- 1980-01-31 LU LU82122A patent/LU82122A1/fr unknown
- 1980-01-31 AT AT0050180A patent/AT376686B/de not_active IP Right Cessation
- 1980-01-31 CH CH79780A patent/CH643856A5/fr not_active IP Right Cessation
- 1980-01-31 DK DK41380A patent/DK146130C/da not_active IP Right Cessation
- 1980-01-31 EP EP80300285A patent/EP0015080B1/en not_active Expired
- 1980-01-31 CS CS80661A patent/CS214695B2/cs unknown
- 1980-01-31 IE IE188/80A patent/IE49504B1/en not_active IP Right Cessation
- 1980-02-01 PH PH23578A patent/PH16214A/en unknown
- 1980-02-01 ZM ZM13/80A patent/ZM1380A1/xx unknown
- 1980-02-01 DD DD80218814A patent/DD151171A5/de unknown
- 1980-02-01 KR KR1019800000401A patent/KR840000281B1/ko not_active IP Right Cessation
- 1980-02-01 ES ES488235A patent/ES488235A0/es active Granted
- 1980-02-01 PL PL1980221747A patent/PL120815B1/pl unknown
- 1980-02-01 FI FI800301A patent/FI67085C/fi not_active IP Right Cessation
- 1980-02-01 SU SU802877703A patent/SU999976A3/ru active
- 1980-02-01 MW MW7/80A patent/MW780A1/xx unknown
- 1980-02-01 OA OA57012A patent/OA06452A/xx unknown
- 1980-02-01 MX MX808622U patent/MX6641E/es unknown
- 1980-02-01 RO RO80100059A patent/RO79330A/ro unknown
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