CS266472B1 - Preparation method of n-arylderivatives n',n'-dimethylurea - Google Patents
Preparation method of n-arylderivatives n',n'-dimethylurea Download PDFInfo
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- CS266472B1 CS266472B1 CS854168A CS416885A CS266472B1 CS 266472 B1 CS266472 B1 CS 266472B1 CS 854168 A CS854168 A CS 854168A CS 416885 A CS416885 A CS 416885A CS 266472 B1 CS266472 B1 CS 266472B1
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- mojih
- οοηοβηογο
- bemectba
- dimethylurea
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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1 266472 0I1HCAHHE H30BPETEHHR K ABTOPCKOMY CBHflETEJIbCTBy3a«BneHo: 15.02.833axBKa: P 3552426/23-04MKH3: C 07 C 127/19; C. 07 C 127/15
Abtopm: T.M.lHaMcyrrtHHOB, 3.M.nany3KTOBa, P.E.BajiHTOB, C.B.CKnap, B.A.ChmohobA.B.CTapKos 3aHBHTejtí>: π/a B-8771
?Ha3BaHHe H3o6peTeHHa: CIIOCOB ΠΟΠΥΗΕΗΗΒ N-APHJElPOH3BOí(HbIX ν',Ν'-,ΠΗΜΕ-. THHMOHEBHHBI ll3o6peTeHne othochtch k ycoBepmeHCTBOBaHHOMy cnoco6y noJiyaeHna N-apHJi-np0H3B0flHfelX N ',N'-«ΜΜβΤΚΠΜΟΗΘΒΗΗΜ O6meň φορΜγΠΜ
PJlH'^6opt6bI C COpHHKaMH.
IÍ3B6CTeH cnocoS nonyaeHna coeflHHeHHa 4>opMynu I (R / R2 = R j. = H, R3 = OCH^, R+ = Cl Br) BSaHMOfleňCTBHeM 3KBHMOJiapHbIX KOJIHUeCTB flHMeTHJiaMHHa η 3-χπορ-(κπΗ -6pom)--4-MeTOKCH<beHHnH3OUřiaHaT.OB b boohom pacTBope πρκ 5^-10°C (CH, A, 466943).Cnoco6 o6ecneaHBaeT Bbicoxne bhxqhh uaneBbix προ,ηγκτοΒ (90-95Z).
Cnoco6 xapaKTepH3yercH ncnojn,3OBaHneM aopornx h TpyaHOflocTynHbix H3oijna-HaTOB, b nponecce cnHTe3a κοτορωχ Hcnooih3yeTca βηοοκοτοκομμημη φοοΓβΗ. - 2 - 266472 ·' HanOonee 6jih3xhm k HacTOHmeMy no TexHnnecxoň cymHOCTH n nocTnráeMOMy pe—3yn&TaTy ηβπηθτοη cnoco6 nonyneHna coennHeHnň φορΜγπΗ I B3anMoneňcTBHeMcepooxncn yrnepofla c. αημ6τη.π3μηηομ b Tonyone npn οοοτηοπιθηηη Ha3BaHHbix pea-reHTOB 1:1:7 n xoMiiaTHoň TeMnepaType c nocnenyiomeií o6pa6oTXon βχβηπο,πηρημμno oTHomeHHio κ cepooxncn yrnepona xojinnecTBOM cooTBeTCTByiomero 3aMemeHHoroarauíMHa npn TeMnepaType 80-98°C (US, A, 2655534) . ΠρηΒβηβΗΗΜή b (2) axcne-pHMeHTajibHbiň npHMep nponecca c ynacTrieM b xanecŤBe 3aMéi4eHHoro aHHJiHHa,n-xnopaHHJiHHa noxa3biBaeT, hto coeflHHeHne I (R,, = R2 = R4 = R^ = H, R3 = Cl)nonynaeTCH c BbixonOM 72,5%. Cnoco6 xapaxTepH3yeTca hh3khm BbixoflOM neneeoronpoflyKTa.
Uejibio HsoSpeTeHHH HBjíHeTCH noBbnueHHe Bbixona neneporo nponyxTa.IIocTaBneHHaH nenb flocTHraeTcn cnocoSoM nonyneHHH N-apnnnpon3BOflHbix ΝΖ,Ν* - -ňHMeranMoneBHHbí (fropMyjibi I, rne R,, R4, R5 = H, CH^, C2H5; = H, Cl, CF3;
Rj = H, Cl, OCHj, CH3, nyTeM B3anMoneňcTBna nnMeTHjiaMHHa c cepooxncbio yrne-pofla b cpene TeTpaxjiopsTHJieHa npn TeMnepaType 5-20°C η mojibhom οοοτηοπιθηηηflHMeTHjiaMHHa n cepooxncn yrnepofla 2,75 —4:1c nocnenywmen o6pa6oTXon
rne R, - Rg ΗΜβιοτ BbnneyKa3aHHbie 3HaneHHH, npn TeMnepaType 90-92aC. OTJIHHHTeJIbHblMH πρΗ3Η3Χ3ΜΗ H3O6peTeHHH HBJIHIOTCH TeMnepaType B3aHMOfleňCT-bhh flHMeTHjiaMHHa c cepooxncbio yrnepona 5 - 20°C, MonbHoe cooTHomeHne flHMe-THjiaMHHa x cepooxncn ymepona 2,75-4:1, Hcnojib3OBaHne B xanecTBe oprarainec-κογο pacTBopHTejia TeTpaxnop3THJieHa. IIcnonb3OBaHHe H36brrxa flHMeTunaMHHa no οτηοιπθηηιο k cepooxncn yrneponacBbnue 4:1 Henenecoo6pa3Ho, Tax xax πρηΒΟηητ κ HeonpaBnaHHo SonbinoMy pacxonyaMHHa.. IIpoBenenne peaxnnn npn TeMneparypax Hnise 5°C Henejiecoo6pa3Ho, Taxxax npnBOflHT x ycnowHeHnio TexHonornn nponecca b cbh3h c Heo6xoflHMocTbio nofl-flepacaHHH HH3xoň TeMnepaTypbi. Ιΐ3θ0ρετβΗΗβ HJimocTpnpyeTCH npnMepaMn 1-14.
CpaBHHTenbHbiň npnMep 15 noxa3biBaeT HenenecoočpaaHOCTh npnBeneHHH nponeccanpn cooTHomeHHH nnMeTHjiaMHHa x cepooxncn yrnepona MeHee 2,7-1. CpaBHHTejib—Hbiň npHMep 16 noxa3biBaeT Henejiecoo6pa3HocTb npoBeneHHH nponecca npn TeMnepa-Typax Bbnne 20° C. ·, Π p η μ e p 1 . . . B xojičy, conepjicamyio 100 mu TeTpaxnopsTHJieHa, npn TeMnejiaType_ 10-15°C npo- nycxawT b TeneHne 1,5 naca. 8,4 r (0,14 mojih) cepooxncn yrnepona n 25,4(0,56 Monen) nnMeTHjiaMHHa, μοπβηοΒ cooTHoiueHne 1:4. 3aTeM flo6aBjiHWT 20 r(0,127 mojih) II (R < = R4 = Rg = H, R2 = Cl, R?= 0CH3) noflHHMaioT TeMnepaTy-py no 92°C n BbjnepjKHBaioT b Tenenne 12 η, Οτγοηηιοτ Η36μτοχ nuMěTnnaMHHa, paa-6aBJiaioT octhtok ropaneň Bonoň,. oxnaisnaioT no χομηητηοη TeMnepaTypbi, BbmaBmnňocaflox OTdmnbTpoBbiBaioT, npoMbiBaioT xononHoň Bonoň n cymaT. IIonynaioT 28,5 r(R1 - R4 = R$ - H, R2 = Cl, Rj - OCH3). TeMnepaTypa miaBneHHH 126-127°C.Bbixon 98,2%, conepjsanne ochobhoto BémecTBa 99,85%. 266472
Π ρ η M e ρ 2. , Προρεοο Ββογτ κβκ b npHMepe 1, ho κοπηηθοτβο αημβτηπβμηηη cocTaBjíHeT!l8,86 r (0,42 mojih), cooTHomeHHe flHMeTunaMHHa a cepooKHCH yrnepo«a 3:1. Πο-jiynaioT 28,3 r (R, = .R+ = R5 = H, R^ = Cl, R3 = OCH3) Bbixofl 97,52. Π p η m e p. 3. Προρεοο Benyr kbk b npHMepe 1, ho κοπηηθοτβο cepooKHCH ymepofla cocTaB-jiHeT 13,44 r (0,22 mojih), flHMeTHJiaMHHa 40,32 r (0,89 Moneft), b KauecTBe npo-η3βοηηογο anHJiHiia HcnonbáytóT II (R4 = R4 = R5 = H, R2 = Rj= Cl) b KOJiHne-cTBe 33 r (0,2 mojih) . nonynaioT 46,5 r (97,92) I (R,, » R4' ~ Rs' = H, R 2 = R3 = = Cl), TeMnepaTypa nJiaBJíeHHH 158- 9 C, conepxaHHe. οοηοβηογο BemecTBa 99,52. . Π ρ Η M e p 4 . ílpoiječc BeayT κβκ b npHMepe 1, ho KannuecTBO cepooKHČH yrnepona cocTaBJín-θτ 15,53 r (0,25 Mojieň) flHMeTHJiáMHHa 34,9 r (0,77 MOJieft), MOJibHoe cooTHome- j HHe HHMeTHJiaMHHa K cepooKHCH yrjiepofia 3,1:1. B KanecTŠe προη3βο,π;ηογο ηηηπη— ' Ha Hcnanh3ywT II (R< = Ř2 = R4 = R? = H, R3 = Cl) b . KoriHHecTBe 30 r (0,23 mo- Í jih). nojiyqaraT 45,8 r (9’8,22) I (R^ = R 2 = R4 = R5· = H, R3 = Cl) TeMnepáTy-pa ruiaHneHHH 174- 5°C, coflepwaHne οοηοβηογο BemecTBa 99,62. Π p ji m e p 5. B KOJi6y no 100 mji TeTpaxnopsTHJieHa npH TeMnepaType 10-15°C nponycKaiOT14,19 r (0,22 mojih) cepooKHCH yrjiepopa h 31,9 r (0,7 mojih) ηημθτηπημηηη,οο—OTHonieHHe HHMeTHJiaMHHa κ cepooKHCH yrnepopa 3,2:1. 3aTeM flo6aBjiHWT 20 r(0,2 mojih) npoH3BOflHOro aHHJiHHa II (R^ - Rs = H) . TeMnepaTypy noflHHMawT po90°C, cMecb nepeMeniHBaioT b TeneHne 2 nacoB, očpačaTbiBaioT KaK b npHMepe -1.ÍIonyiiaioT 34,2 r (972) I (R< ~ R5 = H) TeMnepaTypa ruiaBjíeHHH 135- '6°C, co-flepacaHHe οοηοβηογο BemecTBa 99,72. Π p η μ e p 6.
Ilpouecc seflyT κβκ b npHMepe 1, ho TeMnepaTypa nepeoft CTapHH cocTaBJíneT .15°C, KonimecTBo cepooKHCH yrnepona (15,53) (0,25 mojih) , RHMeTHJiaMHHa 39,7 r(0,875 mojih) cooTHoinenHe nHMeTHnaMHHa κ cepooKHCH yrnepona 3,5 : 1, b Kane-CTBe npoH3BOflHoro a trním Ha Hcnojib3yioT 36,7 r (0,228 Moneň) II (R< = R3 = R4 == = R5 = H, R2 “ CF3) . noJiyyaiOT 52,4 r (98,42) I (R < - R^ = R4 = Rs = H, R2 = = .CFj), TeMnepaTypa nJiaBJíeHHH 163- 4°C, coflepwaHHe οοηοβηογο BemecŤBa 99,32. Π p η m e p 7. npoiiecc Be/iyT κβκ b npHMepe 1, ho TeMnepaTypa nepBoň CTaflHH 10°C, κοπΗηε-ctbo cepooKHCH yrnepona 12,3 r (0,2 mojih), HHMeTHjiaMHHa 27 r (0,6 mojih), ab KanecTBe npoH3Bonnoro atouiHiia Hcnonb3yrot II (R, = R4 = Rs = H, R2 = Cl, R3 =? CF3) b KojiHHecTBe 25,47 r (0,18 mojih). IIonynaioT 37,52 r (98,12) I (R4 = = R+ = R5 = H, R4 = Cl, R3 = CH3) , TeMnepaTypa nnáBJíeHHH 147- 8°C, conep- waHHe οοηοβηογο BemecTBa 98,92. Π p η m e p 8. , Ilpopecc BeflyT κβκ b npHMeRe 1, ho TeMnepaTypa nepBoň CTaflHH 20°C, κοπηηθ-ctbo cepooKHCH yrnepona 13,2 r (0,22 mojih) αημθτηπημηηη 27 r (0,6 mojih), co-oTHOmeHHe flHMeTHJiaMHHa κ cepooKHCH 2,75:1, b KanecTBě npoH3BOflHoro aHHJiHMaHcnojib3yMT II (R, = R5 - C2H 6, R2 - R4 = H) b KOJiHuecTBe 30 r (0,2 mojih) .natiynaioT 43,34 r (98,52) I (R< = R3 = C2Hj., R2 - R4 = H), TeMnepaTypa ruiaB-neHHH 184- 5°C conepxaHHe οοηοβηογο BemecTBa 99,42. Π p η m e p 9.
Ilpopecc BenyT, KaK b npHMepax 1, 6, ho KonunecTBo cepooKHCH yrnepona13,2 r (0,22 mojih), nHMeTHJiaMHHa 31,5 r (0,7 mojih), cooTHomeHHe αημθτηιιπμη—
Ha k cepooKHCH yrnepona 3,2 : 1, b xanecTBe npoH3BonHoro aHHJiHHa Hcnonb3yioTII (R, = CHj, Rs = C2H5, R2 - R4 = H) b KOJiHHecTse 27,2 r. (0,2 mojih). Ilony-ina jot 40,5 r (98,42) I (R< = CH3, Rg. = C^Hg., R2- R4 = H), TeMnepaTypa nnaB-JiemÍH 147- 8 C, copepjKaiiHe οοηοβηογο BemecTBa 99,42. - 4 - 266472 • Π ρ η μ e ρ 10.
Ilpopecc Ββ«γτ, κεκ β npHMepax 1, 9, ho TeMnepaTypa nepBoíí CTaflHH 10°C,b xanecTBe npoH3BOflHoro aHmiHHa Hcnonb3ywT 24,4 r (0,2 μοπη) II (R, = Ra = 2 GH3> R2. = r4 - R$ = H) . ÍIonynaioT 37,78 (98,4%) I (R, = R3 = CH3,’r. = R*. - - H), TeMnepaTypa nnaRneHHH -135— 6 C, coflepxaHHe οοηοβηογο BemecTBa 99,5%. Π ρ η m e ρ 11.
Ilpopecc BenyT, KaK b npHMepax 1, 9, ho TeMnepaTypa nepBoň CTaflHH 20ffC bxaqecTBe προη3βοαηογο aHHflHHa Hcnojib3ýioT 24,4 r (0,2 μοηη) II (R f = R4 ~ - CHj, R2 - R3 = Rg = H) . nonyqaioT 37,8 r (98,5%) I (R^ » R+ = CHg, R2 = 7 R3 ~ Ry = H)> TeMnepaTypa nnaBneHHH 138- 9°C, coflepxaHHe οοηοβηογο Beme- cTBa 99,3%. Π ρ η m e ρ 12. '
Ilponecc Be«yT, xax b npHMepax 1, 9, ho TeMnepaTypa nepBoň cTa/pa 15eC, BjjcanecTBe προη3βοαηογο ammana Hcnonb3yioT 20,8 r (0,2 mohh) II (R2 = CH3, R, = R3 = R4 = Rs = H) . IlonynaioT r (98,4%) I (R2 = CH3, R, = R3 = R4 -= Rs = H), TeMnepaTypa nnaBneHHH 144- 5°C, coflepacainte οοηοβηογο BemecTBa,99,4%. Π ρ η m e ρ 13. · *
Ilponecc BenyT, ksk b npHMepe 1, ho TeMnepaTypa nepBoň CTaflHH (B3aHM0fleŘ-ctbhh cepooKHCH yrnepófla c flHMeTHnaMHHOM) 5°C. Bbixofl I (R( = R4 = Rg = H, R2 = Cl, R3 = OCH3) 98,1%, coflepHtaHHe οοηοβηογο BemecTBa 99,8%. Π ρ η m e p 14.
Ilponecc BenyT, Kax b npHMepe 1, ho TeMnepaTypa. nepBoň CTaflHH 20 C. -BbixoflI (R., = R4 = Rý-= H, R4 = Cl, R3 = OCHj) 98,04%, coflepxaHHe οοηοβηογο Beme-cTBa 98,8%. Π p h m e p 15 (cpaBHHTenbHbiň).
Ilponecc BenyT, xaK b npHMepe 1, ho KonHnecTBO flHMeTHnaMHHa 12,5 r(0,27 mojih) , cooTHomeHHe flHMeTHnaMHHa η οεροοκκοκ yrnepofla 1,9 : 1, Bbixofl I(R = R4 = R5- = H, R-2. = Cl, Rj = OCHj), 88,9%, TeMnepaTypa nnaBneHHH 121-J^C, coflepraaHHe οοηοβηογο BemecTBa 92,7%.
CpaBHeHHe peáynbTaTOB c nonyqeHHUMH b npHMepe 1 noKÓ3biBaeT, ητο yMeHbUie-HHe cooTHonieHHH flHMeTHnaMHHa h cepooKHCH yrnepófla BM3biBaeT nafleraie Bbixofla hHHCTOTbi ijeneBoro'npoflyicra. Π ρ η m e ρ 16 (cpaBHHTenbHbiň).
Ilpoflecc BenyT, xax b npHMepe 4, ho TeMnepaTypa nepBoň CTaflHH 25°C. Bh-χοα I (R« = R2 - R4 = R5 = H, R3 - Cl) 90,0%, coflépacaHHe οοηοβηογο BemecT-Ba 90,8%. , CpaBHeHHe pe3ynbTaTOB c nonyneHHbíMH b npHMepe 4 noxa3biBaeT, hto yBenHne-.-,'HHe TeMnepaTypw B3aHMOfleňcTBHH flHMeTHnaMHHa c cepooKHCbio yrnepófla πρηβοαητ κ. noHHJKeHHío Bbixofla h hhctotm neneBoro npoflyKTa, ΠρΗΜβρΗ 1-14 nOKa3biBaioT, ίτο cnoco6 nonyqeHHH coeflHHeHHň I β οοοτεετοτ-bhh c H3o6peTeHHeM no3BonneT noBbicHTb Bbixofl peneBbix npoflyKTOB.H oBecnenn-BaeT hx BbicoKyKi nHcTOTy.
ΦΟΡΜΧΠΑ H30BPETEHHB
Cnocoó nonyneHHH N-apňnnpoH3BOflHbix Ν/,Ν7-ηΗΜβτΗΠΜοηβΒΗΗΜ oBmeň 4>opMynbi: 266472
rfle R<, R4, Rg = H, CH,, C2Hs; R^, = H, Cl, CF^; R, = H,. Cl, OCHg, CH3B3aHMOfleřicTBHeM flHMenuiaMHHa c cepooKHCbio yrnepofla b oprammecKOM pacTBopiiiTene c nocrienyioiueň o6pa6oTxoír προη3ΒΟ«ημμ amíJiuHa oSíueň «fcopMynbi:
(II) ryje. R< - Rj ΒΜβιοτ BbimeyKa3aHHbie 3HaneHHH, πρκ TeMnepaType 90-92°C, o τ π h-wawinHňčH τβΜ, ητο, c uenhio ποβηιπθηηη Bbixofla uenesoro npoflyxTa, B3an—MOfleňcTBHe flHMeTiinaMHHa cepooKHCbio yrnepofla προβο,βητ lípu TeMnepaType 5-20 C ,h MonbHOM cooTHoineHHH flHMeTHjiaMHHa n cepoOKHCH yrnepofla 2,75-4:1, a b Káně-/CTBe opraHunecKoro pacTBOpHTejiH Hcnonb3yioT TeTpaxnopaTwieH. ... y f t ' *·
Cnocofí nonyneHHH N-apHJinpoH3Bop;Hbix N ,Ν -ρ,ΗΜετΗΠΜοηβΒΗΗΜ o6meň. 4>opMynbi:
rne R|, R^, Rg. = H, CHg, C2R5’, R^ - H, Cl, ČF^jRj = H, Cl, OCHj, CHj ,3aKJiionaeTCH bo B3anMoneňcTBnn flHMeTnna'MHHa c cepooKHCbio yrnepcma tipu hx MOJibBOMcooTHoineHHH 2,75-4:1 h TeMnepaType 5-20°C b TeTpaxnopáTHjieHe c nocneflyromeň
(xi) - 6 - 266472 r-fle R4 - Ř$ ΗΜθίοτ nbímeyKasaHHbie 3HaaeHHH. Πρη3Η3ηο Η3θ6ρβτβΗΗβΜ no pe3ynbTaTaM 3KcnepTtí3t>i, ocymecTBJíéHHoií rocynapČT-BCHHblM KoMHTeTOM CCCP ΠΟ ββΠβΜ Η3θ6ρθΤβΗΗϋ Η ΟΤΚρΜΤΗβ.
Claims (1)
- 266472 PTÍBDMŽT VYNÁLEZU Způoob výroby N-arylderivátů N*, N* - dimethylmočovinyobeoného vzorce Ikde R,, R., Βς - H,CH,, C?Hr í R? = H,C1, CK,} R^ » H,01, OCH3, 0H3 reakcí dímethylaminu ee sulfidem karbonylu v organickémrozpouštědle a následujícím zpracováním produktu derivá-tem anilinu obecného vzorce Ií/11/, kde R^-Rj. mají výše uvedené významy, při teplotě 90 až92 °C, vyznačující se tím, že,se reakce dímethylaminuse sulfidem karbonylu provádí při teplotě 5 až 20 °0 amolovéra poměru dímethylaminu a sulfidu karbonylu 2,75 až4 i 1 a jako organické rozpouštědlo se používá tetrachlor-ethylen. UŽgorodský Azýrobne-poiygraf ický podnik, Gagarina, 101, Uzgorod(ř 1877, Cena 2,40 KČs
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DD85277222A DD263192A3 (de) | 1983-02-15 | 1985-06-10 | Verfahren zur darstellung von n-arylderivaten des n',n'-dimethylharnstoffes |
CS854168A CS266472B1 (en) | 1983-02-15 | 1985-06-11 | Preparation method of n-arylderivatives n',n'-dimethylurea |
BG70645A BG46960A1 (en) | 1983-02-15 | 1985-06-12 | Methodf or preparing of n-aryl derivatives of n, n- dimethyl carbamide |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SU3552426/04A SU1119310A1 (ru) | 1983-02-15 | 1983-02-15 | Способ получения n-арилпроизводных- n′, n′ -диметилмочевины |
DD85277222A DD263192A3 (de) | 1983-02-15 | 1985-06-10 | Verfahren zur darstellung von n-arylderivaten des n',n'-dimethylharnstoffes |
CS854168A CS266472B1 (en) | 1983-02-15 | 1985-06-11 | Preparation method of n-arylderivatives n',n'-dimethylurea |
Publications (2)
Publication Number | Publication Date |
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CS416885A1 CS416885A1 (en) | 1988-02-15 |
CS266472B1 true CS266472B1 (en) | 1990-01-12 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CS854168A CS266472B1 (en) | 1983-02-15 | 1985-06-11 | Preparation method of n-arylderivatives n',n'-dimethylurea |
Country Status (3)
Country | Link |
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BG (1) | BG46960A1 (cs) |
CS (1) | CS266472B1 (cs) |
DD (1) | DD263192A3 (cs) |
-
1985
- 1985-06-10 DD DD85277222A patent/DD263192A3/de unknown
- 1985-06-11 CS CS854168A patent/CS266472B1/cs unknown
- 1985-06-12 BG BG70645A patent/BG46960A1/xx unknown
Also Published As
Publication number | Publication date |
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BG46960A1 (en) | 1990-04-16 |
CS416885A1 (en) | 1988-02-15 |
DD263192A3 (de) | 1988-12-28 |
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