IL95107A - Process for the preparation of 1,1-bit 4-chlorophenyl (-2,2,2-trichloroethanol - Google Patents
Process for the preparation of 1,1-bit 4-chlorophenyl (-2,2,2-trichloroethanolInfo
- Publication number
- IL95107A IL95107A IL9510790A IL9510790A IL95107A IL 95107 A IL95107 A IL 95107A IL 9510790 A IL9510790 A IL 9510790A IL 9510790 A IL9510790 A IL 9510790A IL 95107 A IL95107 A IL 95107A
- Authority
- IL
- Israel
- Prior art keywords
- chlorophenyl
- compound
- dicofol
- trichloroethanol
- bis
- Prior art date
Links
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims abstract description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002576 ketones Chemical class 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 53
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 25
- 238000011084 recovery Methods 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- 238000001816 cooling Methods 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- -1 cycloalkyl ethers Chemical class 0.000 claims description 11
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 10
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- CVUGPAFCQJIYDT-UHFFFAOYSA-N 1-chloro-2-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=CC=C1Cl CVUGPAFCQJIYDT-UHFFFAOYSA-N 0.000 claims description 9
- LUXSISXJGNCOKN-UHFFFAOYSA-N 2,2,2-trichloro-1-(2-chlorophenyl)-1-(4-chlorophenyl)ethanol Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 LUXSISXJGNCOKN-UHFFFAOYSA-N 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- ZDYJWDIWLRZXDB-UHFFFAOYSA-N 2,2-(2-Chlorophenyl-4'-chlorophenyl)-1,1-dichloroethene Chemical group C=1C=CC=C(Cl)C=1C(=C(Cl)Cl)C1=CC=C(Cl)C=C1 ZDYJWDIWLRZXDB-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 3
- 150000001491 aromatic compounds Chemical group 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000008282 halocarbons Chemical class 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 241000238876 Acari Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- VLTYTTRXESKBKI-UHFFFAOYSA-N (2,4-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VLTYTTRXESKBKI-UHFFFAOYSA-N 0.000 description 1
- HTHGRQSFMYIQHB-UHFFFAOYSA-N 1-chloro-4-[2-(4-chlorophenyl)ethyl]benzene Chemical group C1=CC(Cl)=CC=C1CCC1=CC=C(Cl)C=C1 HTHGRQSFMYIQHB-UHFFFAOYSA-N 0.000 description 1
- ZWBANJRSWNLUEP-UHFFFAOYSA-N 2,2,2-trichloro-1,1-bis(2-chlorophenyl)ethanol Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)(Cl)Cl)(O)C1=CC=CC=C1Cl ZWBANJRSWNLUEP-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- UCNVFOCBFJOQAL-UHFFFAOYSA-N DDE Chemical compound C=1C=C(Cl)C=CC=1C(=C(Cl)Cl)C1=CC=C(Cl)C=C1 UCNVFOCBFJOQAL-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000003713 acetylimino group Chemical group [H]C([H])([H])C(=O)N=[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 229910002055 micronized silica Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/08—Ethanol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
- C07C29/92—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound by a consecutive conversion and reconstruction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fireproofing Substances (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL11243390A IL112433A (en) | 1989-07-18 | 1990-07-17 | Combined compounds of 1,1-bis) 4-chlorophenyl (-2,2,2-trichloroethanol and a process for their preparation, and their use in controlling plant mites |
| IL11243395A IL112433A0 (en) | 1989-07-18 | 1995-01-24 | Addition compounds of 1,1-bis (4-chlorophenyl)-2,2,2-trichloroethanol and a process for the preparation thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES8902527A ES2013962A6 (es) | 1989-07-18 | 1989-07-18 | Procedimiento para la obtencion del 1,1-bis(4-clorofenil)-2,2,2-tricloroetanol a partir del 1,1-bis (clorofenil)-2,2,2-tricloroetanol tecnico. |
| ES9001766A ES2032243B1 (es) | 1990-06-27 | 1990-06-27 | Procedimiento para la obtencion del 1,1-bis (4-clorofenil)-2,2,2-tricloroetanol. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL95107A0 IL95107A0 (en) | 1991-06-10 |
| IL95107A true IL95107A (en) | 1996-05-14 |
Family
ID=26154428
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9510790A IL95107A (en) | 1989-07-18 | 1990-07-17 | Process for the preparation of 1,1-bit 4-chlorophenyl (-2,2,2-trichloroethanol |
| IL11243390A IL112433A (en) | 1989-07-18 | 1990-07-17 | Combined compounds of 1,1-bis) 4-chlorophenyl (-2,2,2-trichloroethanol and a process for their preparation, and their use in controlling plant mites |
| IL11243395A IL112433A0 (en) | 1989-07-18 | 1995-01-24 | Addition compounds of 1,1-bis (4-chlorophenyl)-2,2,2-trichloroethanol and a process for the preparation thereof |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11243390A IL112433A (en) | 1989-07-18 | 1990-07-17 | Combined compounds of 1,1-bis) 4-chlorophenyl (-2,2,2-trichloroethanol and a process for their preparation, and their use in controlling plant mites |
| IL11243395A IL112433A0 (en) | 1989-07-18 | 1995-01-24 | Addition compounds of 1,1-bis (4-chlorophenyl)-2,2,2-trichloroethanol and a process for the preparation thereof |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5081319A (de) |
| EP (1) | EP0409689B1 (de) |
| JP (1) | JPH082816B2 (de) |
| KR (1) | KR920010638B1 (de) |
| CN (4) | CN1039989C (de) |
| AT (1) | ATE120169T1 (de) |
| BR (1) | BR9003486A (de) |
| CA (1) | CA2020920C (de) |
| DE (1) | DE69017965T2 (de) |
| DK (1) | DK0409689T3 (de) |
| ES (1) | ES2069712T3 (de) |
| FI (1) | FI95564C (de) |
| IE (1) | IE72092B1 (de) |
| IL (3) | IL95107A (de) |
| IN (2) | IN172157B (de) |
| NO (1) | NO173273C (de) |
| PT (1) | PT94736B (de) |
| TR (1) | TR27493A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0489140B1 (de) * | 1990-06-22 | 1995-08-02 | Elf Atochem S.A. | Verfahren zur herstellung von 1,1-bis(chlorphenyl)-2,2,2-trichlorethanol |
| PL2604608T3 (pl) * | 2009-11-27 | 2016-02-29 | Adverio Pharma Gmbh | Sposób wytwarzania {4,6-diamino-2-[1-(2-fluorobenzylo)-1H-pirazolo[3,4-b]pirydyn-3-ylo]pirymidyn-5-ylo}metylokarbaminianu metylu |
| CN103483407B (zh) * | 2013-10-10 | 2015-11-18 | 宁夏启元药业有限公司 | 一种硫氰酸红霉素萃取结晶用复合溶媒及萃取结晶方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2663703A (en) * | 1953-12-22 | Purification of stkaight-chain | ||
| US2812280A (en) * | 1954-04-20 | 1957-11-05 | Rohm & Haas | Preparation of bis (halophenyl) trichloroethanol |
| US2812362A (en) * | 1955-10-12 | 1957-11-05 | Rohm & Haas | Preparation of bis (chlorophenyl)-trichloroethanol |
| GB831421A (en) * | 1955-11-28 | 1960-03-30 | Metal & Thermit Corp | ª‡,ª‡ bis (chlorophenyl) alkanols |
| US4042498A (en) | 1973-05-29 | 1977-08-16 | Rohm And Haas Company | Separation of organic compounds by adsorption processes |
| CH658773A5 (fr) * | 1984-05-22 | 1986-12-15 | Nestle Sa | Procede de preparation d'un lait ecreme. |
| US4705902A (en) * | 1985-10-03 | 1987-11-10 | Rohm And Haas Company | DDTR-free 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol |
| JPS62286940A (ja) * | 1986-06-02 | 1987-12-12 | ロ−ム アンド ハ−ス コンパニ− | ＤＤＴｒを含まない１，１−ビス（クロロフエニル）−２，２，２−トリクロロエタノ−ルの製造方法 |
| DE3624911A1 (de) * | 1986-07-23 | 1988-01-28 | Hoechst Ag | Verfahren zur trennung von isomerengemischen aus 1.3- und 1.4-bis-(2-hydroxyhexafluoro-2-propyl)-benzol |
| IL89274A (en) * | 1989-02-13 | 1994-04-12 | Agan Chemical Manufacturers | Process for preparing environmentally safe dicofol |
-
1990
- 1990-07-04 DK DK90401935.3T patent/DK0409689T3/da active
- 1990-07-04 EP EP90401935A patent/EP0409689B1/de not_active Expired - Lifetime
- 1990-07-04 DE DE69017965T patent/DE69017965T2/de not_active Expired - Fee Related
- 1990-07-04 AT AT90401935T patent/ATE120169T1/de not_active IP Right Cessation
- 1990-07-04 ES ES90401935T patent/ES2069712T3/es not_active Expired - Lifetime
- 1990-07-11 CA CA002020920A patent/CA2020920C/en not_active Expired - Fee Related
- 1990-07-13 NO NO903129A patent/NO173273C/no not_active IP Right Cessation
- 1990-07-17 IE IE260090A patent/IE72092B1/en not_active IP Right Cessation
- 1990-07-17 IL IL9510790A patent/IL95107A/en not_active IP Right Cessation
- 1990-07-17 IN IN572/MAS/90A patent/IN172157B/en unknown
- 1990-07-17 IL IL11243390A patent/IL112433A/en not_active IP Right Cessation
- 1990-07-17 PT PT94736A patent/PT94736B/pt not_active IP Right Cessation
- 1990-07-17 FI FI903612A patent/FI95564C/fi not_active IP Right Cessation
- 1990-07-18 JP JP2190342A patent/JPH082816B2/ja not_active Expired - Fee Related
- 1990-07-18 US US07/555,066 patent/US5081319A/en not_active Expired - Lifetime
- 1990-07-18 CN CN90104808A patent/CN1039989C/zh not_active Expired - Fee Related
- 1990-07-18 TR TR00679/90A patent/TR27493A/xx unknown
- 1990-07-18 KR KR1019900010904A patent/KR920010638B1/ko not_active Expired
- 1990-07-18 BR BR909003486A patent/BR9003486A/pt not_active IP Right Cessation
-
1992
- 1992-04-21 IN IN234MA1992 patent/IN173099B/en unknown
-
1995
- 1995-01-24 IL IL11243395A patent/IL112433A0/xx unknown
- 1995-05-20 CN CN95106205A patent/CN1066701C/zh not_active Expired - Fee Related
-
2000
- 2000-05-31 CN CN00117894A patent/CN1319579A/zh active Pending
- 2000-05-31 CN CN00117895A patent/CN1319578A/zh active Pending
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