CS232121B1 - Isolation method of 3-methyl-4-sodium nitrophenoxide - Google Patents
Isolation method of 3-methyl-4-sodium nitrophenoxide Download PDFInfo
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- CS232121B1 CS232121B1 CS832588A CS258883A CS232121B1 CS 232121 B1 CS232121 B1 CS 232121B1 CS 832588 A CS832588 A CS 832588A CS 258883 A CS258883 A CS 258883A CS 232121 B1 CS232121 B1 CS 232121B1
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- methyl
- sodium
- nitrophenolate
- nitrophenoxide
- production
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- 238000002955 isolation Methods 0.000 title claims description 4
- DEQWBYKBSRNLCS-UHFFFAOYSA-M sodium;3-methyl-4-nitrophenolate Chemical compound [Na+].CC1=CC([O-])=CC=C1[N+]([O-])=O DEQWBYKBSRNLCS-UHFFFAOYSA-M 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003849 aromatic solvent Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims 1
- 235000011178 triphosphate Nutrition 0.000 claims 1
- 239000001226 triphosphate Substances 0.000 claims 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 9
- PIIZYNQECPTVEO-UHFFFAOYSA-N 4-nitro-m-cresol Chemical compound CC1=CC(O)=CC=C1[N+]([O-])=O PIIZYNQECPTVEO-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 3-methyl-4-nitrophenyl Chemical group 0.000 description 1
- XGCZABZDVJOWTL-UHFFFAOYSA-N 3-methyl-4-nitrosophenol Chemical compound CC1=CC(O)=CC=C1N=O XGCZABZDVJOWTL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical class O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- XFBJRFNXPUCPKU-UHFFFAOYSA-N chloro-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(Cl)(=S)OC XFBJRFNXPUCPKU-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MJNAIAPNXYJWCT-UHFFFAOYSA-N dimethyl (3-methyl-4-nitrophenyl) phosphate Chemical compound COP(=O)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 MJNAIAPNXYJWCT-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Description
Vynález sa týká izolácie 3-metyl-4-nitrofenolátu sodného z vodného roztoku 3-metyl-4-nitrofenolátu sodného kryštalizáciou.The invention relates to the isolation of sodium 3-methyl-4-nitrophenolate from an aqueous solution of sodium 3-methyl-4-nitrophenolate by crystallization.
Na výrobu prípravkov na ochranu rastlín ako například O,O-dimetyl-O-(3-metyl-4-nitrofenoljtiofosfátu a 3-metyl-4-dimetylamínofenyl-3-metylkarbcnátu sa používá 3-metyl-4-nitrofenol. Z početných spósobov přípravy 3-metyl-4-nitrofenolu sa najčastejšie používajú tieto: reakcia m-toluidínu s kyselinou sírovou a dusitanom sodným, priama nitrácia 3-metylfenolu, hlavně však nitirozácia 3-metylfenoilu na 3-metyl-4-nitrózofenol s následnou oxidáciou na 3-metyl-4-nitrofanol pomocou kyseliny dusičnej, peroxidu vodíka a iných oxidačných činidiel. Oxidáciou 3-uietyl-4-nitrózofenoliu kyselinou dusičnou na 3-metyl-4-nitrofenol popisuje ČSSR AO 146 179. Přípravu 3-metyl-4-nltrofenolu v prostředí roztoku minerálnej kyseliny s následnou oxidáciou 3-metyl-4-nitróizofenolu kyselinou dusičnou popisuje ČSSR AO 149 726. Podobná příprava, avšak v prostředí nižších alkoholov, je v DOS 2 236 571. Produkt sa vo všetkých troch prípadoch získává jeho vykrystalizováním, filtráciou, premytím a vysušením. Čistenie 3-metyl-4-nitrofenolu v přítomnosti vodného roztoku hydrogénsiričitanu sodného alebo draselného popisuje Japonský patent 21 241 (1964). Čistěním 3-metyl-4-nitrofenolu a jeho sodnej soli kryštalizáciou v přítomnosti sodných solí minerálnych kyselin sa zaoberá ČSSR AO 147 502 a je podrobné popísané v článku Macko J., Váňo J., Ďulák K.: Chem próim. 29/54 č. 8, 408 (1979). Vo vyššie -uvedených literatúrnych odkazoch sa nerieši čistenie a výroba 3-metyl-4-nitrofenolátu sodného z roztokov vznikajúcich pri výrobě organických zlúčenín fosforu, pričom jedna reakčná komponenta je 3-metyl-4-nitrofenol a/alebo jeho sodná sol'.3-Methyl-4-nitrophenol is used to produce plant protection products such as O, O-dimethyl-O- (3-methyl-4-nitrophenol) thiophosphate and 3-methyl-4-dimethylaminophenyl-3-methylcarbate. The most commonly used 3-methyl-4-nitrophenol are: reaction of m-toluidine with sulfuric acid and sodium nitrite, direct nitration of 3-methylphenol, but mainly nitritation of 3-methylphenoil to 3-methyl-4-nitrosophenol followed by oxidation to 3-methyl -4-Nitropanol with nitric acid, hydrogen peroxide and other oxidizing agents The oxidation of 3-uietyl-4-nitrosophenol with nitric acid to 3-methyl-4-nitrophenol is described in Czechoslovakia AO 146 179. Preparation of 3-methyl-4-nitrophenol in solution environment mineral acid followed by oxidation of 3-methyl-4-nitroisophenol with nitric acid is described by ČSSR AO 149 726. A similar preparation, but in the environment of lower alcohols, is in DOS 2,236,571. Crystallization, filtration, washing and drying Purification of 3-methyl-4-nitrophenol in the presence of aqueous sodium or potassium bisulfite solution is described in Japanese Patent 21,241 (1964). The purification of 3-methyl-4-nitrophenol and its sodium salt by crystallization in the presence of sodium salts of mineral acids is dealt with in CSR AO 147 502 and is described in detail in Macko J., Vano J., Dulak K. Chem. 29/54 č. 8, 408 (1979). The above references do not address the purification and production of sodium 3-methyl-4-nitrophenolate from solutions resulting from the production of organic phosphorus compounds, one reaction component being 3-methyl-4-nitrophenol and / or its sodium salt.
Vyššie uvedené nedostatky sú odstraněné podl'a vynálezu spósobom izolácie 3-metyl-4-nitrofenolátu sodného, podstata ktorého spočívá v tom, že sa 3-metyl-4-nitrofanolát sodný izoluje z vodného roztoku 3-metyl-4-nitrofenolátu sodného, ktorý je znečistěný anorganickými solami, organickými zlúčeninami fosforu, síry a/alebo chlóiru, zvyškami aromatického rozpúšťadla, z výroby 0,0-dimetyl-0-(3-imetyl-4-nitrofenyljtiofosfátu, 3-imetyl-4-mitrofenolát sodný sa oddělí od váčšiny sprievodných nečistot kryštalizáciou v přítomnosti minerálnych solí za teploty 2 až 60 °C, s výhodou 5 až 25 °C. Výhodné sa použije pri procese tlak nižší, ako je tlak atmosférický.According to the invention, the above-mentioned drawbacks are remedied by a process for the isolation of sodium 3-methyl-4-nitrophenolate, characterized in that sodium 3-methyl-4-nitrophenolate is isolated from an aqueous solution of sodium 3-methyl-4-nitrophenolate which is contaminated with inorganic salts, organic phosphorus, sulfur and / or chlorine compounds, aromatic solvent residues, from the production of 0,0-dimethyl-O- (3-methyl-4-nitrophenyl) thiophosphate, sodium 3-methyl-4-mitrophenolate separated from the bulk of accompanying impurities by crystallization in the presence of mineral salts at a temperature of 2 to 60 ° C, preferably 5 to 25 ° C. Preferably, a pressure lower than atmospheric pressure is used in the process.
Postupem podta vynálezu je možné získat 3-metyl-4-nitrofenolát sodný z odpadných vod odpadajúcich z výroby 0,0-dimetyl-O- (3-Ímetyl-4-nitrofenyl jtioíosfátu. Kryštalizáciou 3-metyl-4-nitrofenolátu za vhodné zvolených podmienok je možné dostat produkt velmi dohřej kvality, ktorý je možné opat použiť pri výrobě O,O-dlmetyl-O-(3-metyl-4-nitrofenyljfiofosfátu. Postup je vhodný použit pri odpadných vodách, ktoré obsahujú váčšie množstvo 3-metyl-4-nitrofenolátu sodného a menšie množstvo minerálnych solí. Pri kryštalizácii sa produkt nimi iba nepatrné znečisťuje. Malé množstvo minerálnych solí nie je na závadu pri výrobě O,O-dimetyl-0-(3-metyl-4-nitrofenyl)tiofosfátu. Znížením tlaku pri procese, oproti atmosferickému, sa zabráni znečisteniu pracovného prostredia prchavými organickými zlúčeninami. Realizácia spSsobu podta vynálezu je jednoduchá a nenáročná.According to the process of the present invention, it is possible to obtain sodium 3-methyl-4-nitrophenolate from waste waters resulting from the production of O, O-dimethyl-O- (3-methyl-4-nitrophenyl) thiophosphate. It is possible to obtain a product of very high quality which can be used in the production of O, O-dimethyl-O- (3-methyl-4-nitrophenyl) phosphate. Sodium nitrophenolate and minor amounts of mineral salts Small amounts of mineral salts do not interfere with the production of O, O-dimethyl-O- (3-methyl-4-nitrophenyl) thiophosphate. Compared to atmospheric, contamination of the working environment with volatile organic compounds is avoided.
P r i k il a d 1Example 1
O,O-dimethyl-O-(3-methýl-4-ni.trofenyl)tiofostát sa připravil kondenzáciou 0,0-dimetylchlórtiofosfátu s 3-metyl-4-nitrofenolátom sodným v přítomnosti K2CO3 a toluénu. *O, O-dimethyl-O- (3-methyl-4-nitrophenyl) thiophostate was prepared by condensation of O, O-dimethylchlorothiophosphate with sodium 3-methyl-4-nitrophenolate in the presence of K 2 CO 3 and toluene. *
Nezreagovaný krystalický 3-metyl-4-nitrofenolát sodný spolu s K2CO3 a NaCl sa rozpustil vo vodě. Získal sa 32,4 % hmot. vod- * ný roztok 3-metyl-4-nitrofenolátu sodného, ktorý obsahoval 8 % hmot. K2CO3, chlorid sodný, 0,03 % hmot. toluénu, organické ztúčeniny fosforu stanovené ako organický fosfor 0,11 % hmot. Teplota roztoku bota 70 °C.Unreacted crystalline sodium 3-methyl-4-nitrophenolate together with K 2 CO 3 and NaCl were dissolved in water. 32.4 wt. aqueous solution of sodium 3-methyl-4-nitrophenolate containing 8 wt. K 2 CO 3, sodium chloride, 0.03 wt. % toluene, organic phosphorus compounds determined as organic phosphorus 0.11 wt. Shoe solution temperature 70 ° C.
K 200 ml roztoku sa přidalo 20 g Na2CO3 a po jeho rozpuštění sa nechalo ochladením vykrystalizovat pri teplote 2 °C. Kryštalky sa odfiltrovali. Vo filtráte bolo 0,12 % hmot. organického fosforu a 0,02 % hmot. toluénu. Výťažok 3-metyl-4-nitrofenolátu sodného bol 93,7 % z teorie.To 200 ml of the solution was added 20 g of Na 2 CO 3 and after dissolution it was allowed to crystallize by cooling at 2 ° C. The crystals were filtered off. 0.12 wt. % organic phosphorus and 0.02 wt. toluene. The yield of sodium 3-methyl-4-nitrophenolate was 93.7% of theory.
P r í k 1 a d 2Example 1 a d 2
200 ml roztoku 3-,metyl-4-nitrofenolátu sodného z příkladu 1 sa vyhrialo 11a teplotu varu počas 30 minút. Počas pronesu sa udržiaval mierny podtlak o 5 kPa nižší, ako bol tlak atmosferický. Potom sa roztok doplněním odparenej vody upravil na póvodný objem a teplotu 82 °C. Roztok obsahoval 0,01 % hmot. toluénu a 0,07 % hmot. organického fosforu, 0,05 % hmot. síry a 0,01 % * hmot. chlóru. Ďalej sa postupovalo ako v příklade 1. Vo filtráte bolo 0,08 % hmot. organického fosforu. Výťažok 3-metyl-4-nitrofenolátu sodného bol 92,9 % z teorie.200 ml of the sodium 3-methyl-4-nitrophenolate solution of Example 1 was heated to boiling point for 11 minutes. A slight vacuum was maintained at 5 kPa below atmospheric pressure during the utterance. Then, the solution was brought to its original volume and a temperature of 82 ° C by adding evaporated water. The solution contained 0.01 wt. % toluene and 0.07 wt. % phosphorus organic, 0.05 wt. % sulfur and 0.01 wt. chlorine. The procedure was as in Example 1. The filtrate contained 0.08 wt. organic phosphorus. The yield of sodium 3-methyl-4-nitrophenolate was 92.9% of theory.
Příklad 3Example 3
K 200 ml roztoku 3-'metyl-4-nitrofenolátu sodného z příkladu 1 sa přidalo 20 g aktivovaného bentonitu. Po 1 h sa beintonit odfiltroval. Roztok obsahoval 0,08 % hmot. organického fosforu a 0,02 % hmot. toluénu. Ďalej sa postupovalo ako v příklade 1. Vo filtráte bolo 0,08 % hmot. organického fosforu a 0,03 % hmot. toluénu. Výťažok 3-metyl-4-nitrofenolátu sodného bol 93,4 % z teorie.To 200 ml of the sodium 3-methyl-4-nitrophenolate solution of Example 1 was added 20 g of activated bentonite. After 1 h, the beintonite was filtered off. The solution contained 0.08 wt. % organic phosphorus and 0.02 wt. toluene. The procedure was as in Example 1. The filtrate contained 0.08 wt. % organic phosphorus and 0.03 wt. toluene. The yield of sodium 3-methyl-4-nitrophenolate was 93.4% of theory.
Příklad 4Example 4
Postupovalo sa podlá příkladu 2 s tým rozdielom, že sa postupné snižoval tlak v banke z atmosferického tlaku na tlak 1500 Pa. Znižovanie tlaku sa robilo tak, aby obsah banky inevykypel. Zmes sa súčasne aj adiabaticky chladila. Výťažok 3-metyl-4-nitrofenolátu sodného bol 94,5 % z teorie. Příklad 5The procedure of Example 2 was followed except that the pressure in the flask was gradually reduced from atmospheric pressure to 1500 Pa. The pressure reduction was done so that the contents of the flask were inevitable. The mixture was also adiabatically cooled. The yield of sodium 3-methyl-4-nitrophenolate was 94.5% of theory. Example 5
Postupovalo sa pódia příkladu 2 s týmThe procedure of Example 2 was followed
9 rozdielom, že obsah banky vykrystalizoval pri teplote Θ9 °C. Výťažok 3-metyl-4-nitrofenolátu sodného bol 88,6 % z teorie.9 except that the contents of the flask crystallized at Θ9 ° C. The yield of sodium 3-methyl-4-nitrophenolate was 88.6% of theory.
Vynález je možné použit pri výrobě 3-metyl-4-nitrofenolátu sodného, 'ktorý odpadá pri výrobě O,O-dimetyl-O-(3-metyl-4-nitrofenylj tiof osf átu kondenzáciou 0,0-dimetylohlórtiofosfátu s 3-metyl-4-nitrofenolátom sodným.The invention is applicable to the production of sodium 3-methyl-4-nitrophenolate, which is omitted in the preparation of O, O-dimethyl-O- (3-methyl-4-nitrophenyl) thiophosphate by condensation of O, O-dimethylohlorothiophosphate with 3-methyl- Sodium 4-nitrophenolate.
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| CS832588A CS232121B1 (en) | 1983-04-11 | 1983-04-11 | Isolation method of 3-methyl-4-sodium nitrophenoxide |
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| Application Number | Priority Date | Filing Date | Title |
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| CS832588A CS232121B1 (en) | 1983-04-11 | 1983-04-11 | Isolation method of 3-methyl-4-sodium nitrophenoxide |
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| CS258883A1 CS258883A1 (en) | 1984-05-14 |
| CS232121B1 true CS232121B1 (en) | 1985-01-16 |
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- 1983-04-11 CS CS832588A patent/CS232121B1/en unknown
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