CS248293B1 - Method of polyester production with small stress - Google Patents
Method of polyester production with small stress Download PDFInfo
- Publication number
- CS248293B1 CS248293B1 CS833530A CS353083A CS248293B1 CS 248293 B1 CS248293 B1 CS 248293B1 CS 833530 A CS833530 A CS 833530A CS 353083 A CS353083 A CS 353083A CS 248293 B1 CS248293 B1 CS 248293B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hours
- polyester production
- small stress
- πρη
- nph
- Prior art date
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- 229920000728 polyester Polymers 0.000 title claims 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims 1
- 229930188620 butyrolactone Natural products 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000017399 Caesalpinia tinctoria Nutrition 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 101100227330 Mus musculus Flii gene Proteins 0.000 description 1
- 101100366940 Mus musculus Stom gene Proteins 0.000 description 1
- 241001553014 Myrsine salicina Species 0.000 description 1
- 241000388430 Tara Species 0.000 description 1
- 240000007313 Tilia cordata Species 0.000 description 1
- 101150115538 nero gene Proteins 0.000 description 1
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyesters Or Polycarbonates (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Description
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BnpóqeM b jiHTepaType H3BecTHbi flBa βπΗροορτοοφΗρβ cjiefly»meň φορΜνπΗ:
Ch2 C \/° /c\
0 CH R4 a 1 R R4 H H b H CHjCl CH; ( iCH2 248293 2 KOTOpwe npH cŤaHflapTHferx ycnoBHHX jkh/jkh (Liebigs Ann. Chem, 623, 183, (1959); J. Polytn. Scí., Polyro. Lett. J_8, 1. 25, (1980)). Osuško επκροορτο-3φκρ a HMeeT Ηεοοετετοκ', hto oh upeaBbraaHHo γηγροοκοπηηημη, BcnencTBHeqero, KaK h3bectho, 3HawnTem>HO BO3MymaeTC« κητηοηηηη nojiHMepH33HHH c pac-KpbiTHeM UHKjia h tojibko bo3hhk3k>t nojiHMepbi HH3Koň MoneKynapHoň Maccw. CnHpo-Ορτθ3φκρ b XOTH HBJIHeTCH npOCTO MaHHnyjIHpyeMblM, OflHaKO κβτηοηηηβ nOJlHMepH-3au,HH c pacKpbiTHeM pHKjia co3flaeT npobjíeMbi ποτομυ, hto BcjieflCTBne peaKTHB-hocth xjiopMerajihHoň rpynnbi npOHCXOflHT peaxuHH obpbiea neneft η περε3ετερΗφΗ-Kau,HH, BCjieflCTBHe nero Βθ3ΗΗΚ3ΐοτ tojibko ojmroMepbi, OKpameHHbie b xejiTbiňHBeT. ÍÍ3BGCTGH H ňajIBHeHinHH JKHflKHH εΠΗρθΟρτΟ3φπρ, nOJJHMGpH3yiMHHňca ΤερΜΗ-HGCKH-paflHajlBHblM Η ΚβΤΗΟΗΗΗΜ ΟΠΟΟΟβοΜ Η ΠρΗ KQTOpOM B BbllDG Η33Β3ΗΗθίί φθρ-Myjie R’/R2 npaflCTaBjíeH rpynnoň -CH2 (πετεΗτ JP -121584-79; DE-OS 3035431).OflHaKo b 3tom cjiynae cymecTBeHHMH HGflOCTaTok. aaKjnonaeTcn b tom, mto npe-BpaUIGHHG ΜΟΗΟΜερΟΒ ΠρΗ IIOJIHMepH3HnHH TOJIBKO ΟΗβΗΒ MajlO , T3K MTO HCnOjlh3O-BaHHG nojiyHBHHoro cjiojkhoio ποπΗ3φΗρ3 BQ3MOJKHO tojibko nocjie omhctkh nepe-ocaxneHHeM.
Bce H3BGCTHbie cnupoopTo3φκρω HMeiOT COBMeCTHbIH npH3Hax, MTO nOjmMGpHaaiJHHnpoHcxoflHT c ohghb MajibíM oÓBGMHbíM cxaTHGM (cyMMbi o6meň ycaflKH C 0,5 flO M3KC<2%). BbI3BaH BblPIG OnHCHHHblMH H BbITBKaiOmHMH H3 φΗ3ΗΗεεΚΗΧ H XHMHMeCKHXCBoňcTB, a Tarae H3 ycnoBHň πρη ρεβκιρίΗ ΗεβοετετκεΜΗ, cymocTBeHHbiň Hefloc-T3TOK ypOBHft TGXHHKH 33KJH0HaeTCH Β TOM, MTO flO CHX ΠΟρ HGBO3MO3CHO 6bUIO TeXttHMeCKH HCnOJlb3OBaTb BaXHblň 3φφθΚΤ nOJIHM8pH3aiJHH C MajIblM OÓBGMHblM CMa-THGM ϋΠΗρθθρτθ3φΗρθΒ flJIH nOJiyHGHHH CJlOXHblX ΠΟίΙΗΒφΗρΟΒ C MajIblM ΗΗΠρίΒΚεΗΗεΜΗ HX ΠρΗΜβΗΘΗΗΗ B K3HGCTBG nOJJHMGpHblX φορΜΟΒΟΜΗΜΧ Ma TepnaJIOB HJIH KJIGGB. HGJIb H3OfípGTGHHH :
JlejIBlO ,ηΗΗΗΟΓΟ Η3θ6ρεΤβΗΗΗ HBJIHeTCH npeOflOJieHHe HOflOCTaTKOB ypOBHS TeXHHKH.
B naCTHOCTH OHGHB MajlOe OfiBBMHOe CXaTOe ΠρΗ nOJIHMBpH3apHH εΠΗρΟΟρΤΟΒφΗρΟΒCJÍGflyGT TéXHHHGCKH HCHOJlB3OBaTB flJIH nOJiyHeHHH CJIOSKHBIX ΠΟΠΗ3φΗρθΒ C MajIblM • HanpHWeHHGM, npHHGM OflHOBpGMGHHO C.JIGflyGT 06eCneMHTb 6OJIbHiyi0 CTaSHJIBHOCTBnpH ΧρΗΗβΗΗΗ HCXOflHOH CMGCH MOHOM6pOB flO HeKOTOpbIX HěflejIB H BO3MO3KHyM B TBX“HOjIOTHHeCKOM OTHOIUGHHH flOjiryW 3CH3H8CnOCO6H0CTB fíO 3 flHéň. KpOMG ΤΟΓΟ ΠρΗΧΟ“flHTca ycTpaHHTB ΓΗΓροεκοπΗΗΗοετΒ εηΗροορτθ3φΗρθΒ h flocTHHB nojiHoro npeBpa-meHHH MOHOMGpOB ΠρΗ OflHOBpGMBHHO BblCOKHX MOJTeKyjIHpHbtX MaCC3X. B COOTBGTCT“BHH C nejlbio nOJiynaeMblG CJlOMHbie Π0ΠΗ3φΗρΜ flOJDXHbl 6bITB nOjníOCTBIO 6ecyBeTHbIMHη οπτΗπεεκΗ npO3paMHHMH. H3JlO»GHHe CymHOCTH_H3O6gGTGHMH2 fljiH pGajiH3au;HH nejm 3anaMa naHHoro Η3ο6ρετεΗΗ« - yKaeaTB cnocoC, πρ« πομο- íihh KOToporo BO3MOOTO noflBepraTB nojiHMGpH3aHHH npocTO MaKHnyjiHpyeMbie, CTa- 1ÓHjibHbie h jierKo nojryMaeMbie επκροορτοΒφΗρΜ o6pa3ya cjioxhmg ποβηβΦηρμ c MajibíMHanpaweHHGM.
CornacHO Η3θ6ρετεΗΗΚ» aaflaqa pemaeTCH cboco6óm nojiyneHHH cjioambix ποιπϊβΦηροβC MajIblM HanpHXeHHeM H3 εΠΗρθθρΤΟ3φκρθΒ, OTJTHHaiOnpiMCH TGM, MTO SyTHpOJiaKTOHH H3O6yTHΙΙΓJIHUHnOBblfí 3φΗΡ B MOJIBHOM COOTHOmGHHH 1 S 1 flO 2í 1 B TBTpaXJTOpMGTa“hg b KanecTBe pacTBopHTGna πρκ 30eC Β τεπβΗΗβ 5 qacoB b npHcyTCTBHH BFyEt^Ob KanecTBe KaTajra3aTopa npGBpa®a»T β επκροορτο3φΗρ 2-H3o6yTHJioKCHMGTHn--1.4.6-TpHOKca-cnHpo- [4.4] -HOHaH. llojiytieHHblft TaKHM O6pa3OM 2-H3O6yTHJIOKCH“MGTHJI-1 .4.6-TpHOKca-cnHpo- [4.4] - HOHaH flajiBine cornacHO Η3θ6ρετεκΗΐο ποηΗΜερκ-syeTca hjih oahh hjih c flojiaň ρ,ρ 30 mojibhmx npoyeHTOB pacTBopennoro b hgm h _ 248293 3 nojiynaeMoro no DD-WPC 08G/234816-5 2,2-6hc-(1.4,6-TpnoKca-cnnpo- [4.AJ-ho-HaH-2-ΜβτΗηοκοΗφθΗΗπ)-nponaHa b npucyrcTBHH Et}O+SbCl~ b KOjinnecTBe c 1 Bec.%p;o 3 Bec.% othochtgjibho KojnmecTBa cnupoopTOBíJiHpa npn 80 ,π,ο 100°C b Te4e-HHe 6 no 8 qacoB, lípu stom cnoco6e cornacno n3o6peTeHwo fiocraraeTCH CTa-BHJIhHOCTh npn ΧρβΗβΗΚΗ HCXOflHOň CMeCH MOHOMepOB, COCTaBJIHHMuaH ΗβΚΟ TOpbieHeflenu, 6ea Tóro, utoGm BCTpenajmcb BbineneHHH KpHCTannoB híih flpyrne noMyT-HeHHHj JícxoflHbie MOHOMepbi h cMecn MOHOMepOB He rnrpocKonnHHbi. Wn3Hecnoco6-HocTb HcxoflHOň CMeCH nojinMepn3aijnH cocTaBJíaeT Gojihwe 72 nacoB, BpeMH rene-o6pa3OBaHH« npH 100 G Bce eme okojio 1 qaca, IIojiHMepH3 aipin προΗοχορ,ΗΤ npnnOJIHOM npeBpaníGHHH MOHOMepOB Η ΠρΗΒΟβΗΤ K BblCOKHM MQneRynHpHbtM MaccaMCJ10»HbIX Π0ΠΗ3φΗρ0Β, KOTOpbie ΚρΟΜβ ΤΟΓΟ nojIHOCThlO GeCUBeTHbl Η ΟΠΤΜΗβΟΚΗnpo3paHHM. OG^ee o6f>eMHoe cxame bo apeMH rejieo6pa30BaHHH η οπιηβθηηη b 3a-BHCtoMOCTH OT COOTHOmeHHň ΚΟΜΠΟΗβΗΤΟΒ CMeCH MOHOMepOB COCTaBJIHeT 1 flO 1,6%,nonyneHHbie thkhm ofípaaoM cnoatHbie ποπηβΦηρμ ημθιοτ Manoe HanpaaceHHe h ohhthGkh b nmpoKoň oGnacra TeMnepaTyp. Ohh HenyBCTBHTenbHbí κ o6pa30BaHHio mhk-pOTpemHH h ycToňnHBbi κ pe3KOMy H3MeHeHHro TeMnepaTypbi, Hanp, b oGnacra c-40°G «o +80°C,
OriTHHecKHe fleTaroi H3 cTexna, cKneeHHbie πρκ noMonpt cnocoGa cornacHO H3o6pe-TeHHto, Ka*K jihh3H, nnocKHe nnacTHHbí h nonoGHbie onranecKHe fleTajiH npH kom-HaTHoft TeMnepaType MexaHHUecKH HepašteMHbi. B cnynae HeoGxonHMoera hx mojkhopa3fceflHHHTh HarpeBaHHeM n° 150 C b TeneHHe HecKOjibKHX MHHyT ηπη oGpaGoTKOHΚΗΠΗΒΙΗΜ ΧίΙΟροφορΜΟΜ. ” IIpUMepM KOHKpeTHOrO BbinonHeHHHl
HaoGpeTeHHe nonpoGnee noncHneTCH πρκ πομοπιη cnenywmHX npHMepoa κοΗκρετΗο-ΓΟ BbinOJTHeHHH . ΠρΗΜβρ 1. 172 r (2 mojih) GyraponaKTOHa pacTBOpniOT b 600 mji TeTpaxnopMeTaHa h cMenm-BawT c 6 mji BF?· Et40. ΠρΗ nepeMemHsaHHH floSaBnaioT no xanjiHM 260 r (2 Monb)H306yTHJirjIHlWJ0B0r0 θφκρβ ΠρΗ 30°C B ΤβΗβΗΗβ 2 HaCOB, 3βΤβΜ flaiOT BO3MOJK“HocTb flonojiHHTenbHoň peaKUHH b TeueHHe 3 uacoB h CMemHBaiOT c 300 mji 10%-noro NaOH ívih τογο, htoGm pa3pymHTb xaTajiH3aTop,
OpraHHMecKyw φββγ οτηβΠΗίοτ, cymaT c K2G03 h flHCTHJumpyioT. CHanana ynanaioTpacTBopHTejib, ποτομ ocTaTOK φpaκ^HOHHpywτ b BaxyyMe. nonynawT 250 r cnnpo-ορτθ3φπρβ 2-H3o6yTHjiOKCHMeTHji-l .4,6-TpHOKca-cnHpo-[4.4^j-HOHaH b xanecTBenpo3paqnoň xhakocth. ŤoMKa ΚΗπεΗΗΒί 72 no 74°C/33 MÚa ='»1,4438; p10 =c 1,0383 r· cm’5 C « H20()4 BbWHcjieHo: C 61,09% H 9,32% (216,24) HaňnóHo: C 60,93% H 9,39%
OflHHaKOBbie pe3yjibTaTbi nojiynaioTca h npn Hcnonb3OBaHHH 130 r (1 mojib) hso-GyTHJirjlHUHnOBOrO 3φΗρΒ,
B 10 r 2-H3o6yTHjiOKCHMeTHJi-l .4.6-TpHOKca-cnHpo-[4,4j-HOHaHa npH 40 ρ,ο 50°CnpH nepeMeiuHBaHHH pacTBopaioT. 0,1 r EtjO ' SbClé , 3τβ roTOBaa κ ynoTpeGneHHioHcxo/jHan cMecb nojiHMepH3an,HH b 3axpbiTOM cocyne cnocoGHa κ πρημθηθηημ 3 ηΗΗh nojiHMepMsyeTCH npri 100°C b TeneHHe 8 nacóB b 33κρητομ Φορμοβοηηομ cocynehjih khk KJieeBoíí cnoň Me»ny onrayecKHMH fleTajwMH o6pa3yn GeciíBerabiň, onra-MecKH npo3panHbiň cnoxHbiň ποηποφηρ c MajibíM HanpnweHHeM oGmeň φopMyπbI (-CHj-CHj-CHj-C-O-CH-CHj-O)- / 0 CH, O-CHj-CHÍCH,)* 248293 4 rp,e n=10 po 15 h ofimaa oGbeMHaa yca^Ka cocTaBJíaeT 1,6%.
TeMnepaTypa cTeKjioBaHHH (T8) cnoiHor.o nojin9<i>npa cocTaBJíaeT -35 C, ero πηοτ- hoctb - p2° = 1,055 r · cm~ . ngHMeg_2
PacŤBop 20,506 r (0,04 Mojib) 2,2-6hc-(1 .4.6-TpnoKca-cnnpo- [4.4]-ηοη8η-2--MeTHjioKCH(beHHJi)-nponaHa - nonyneHHoro no DD-WP C 08G/234816-5 - b 25,95 r(0,12 MOjib) 2-H3o6yTHJioKCHMeTHJi-l .4.6-TpHOKca-cnnpo- [4.4]-HOHaHa - nonyneH*Horo KaK yKaaaHo b npHMepe 1 - CMeraHBaioT c 0,75 r Et}Ó SbClfi. íÍHHixuaToppacTBopaioT npH 40.flo 50°C h nepeMeniHBaHHH h HcxoflHaH cMecb nonHMepH3auHHJOKpaiueHHaa b ^ejiTbiň η,Ββτ, KOTopaa πρκ κομη3τηοη teMnepaType b 3εκρ«τοΜ co-cy#e coxpaMeT cnocofíHocrb κ npuMeHeHHW b Tenemie HecKonbKHX flHeň, 3aTeMnonnMepH3yeTCH npH 100°C b Tepejme 6 nacOB b, 33κρμτομ φορΜΟΒΟΗΗΟΜ cocy^eHnu Kax KJieeBOň cnoň MexKfly οπτΗηεοκκΜΗ fleraňaMH. Bo3HHKHyTbiň cnoacHbiň nojiH-ΟφΗρ - fíeCUBeTHbIH Η OnTHHéCKH npO3paHHbIH. IljIOTHOCTb COCTaBJÍHeT p10 = = 1,117 r · cm' i . O6ntaa oSbeMHaa yca^Ka bo BpeMH npouecca nonHMepH3anHH coc-TaBJíaeT 0K0.n0 1%. $opMyna_H3o6geTeHHa
Cnoco6 nonyneHHH cnoatHbix ποπΗ3φΗροΒ c MajibíM HanpnxceHHeM H3 οπκροορτο3φΗροΒ,OTnunaEiinHHCH τθμ, ητο npeepamaroT SyraponaKTOH h Η3ο6γτΗπΓΠΗφί#θΒΜΗ 3φκρ bMonbHOM cooTHomeHHH lil p;o 2:1 b TeTpaxnopMeTane b KanecTBe pacTBOpuTenHπρκ 30*0 b TeneHne 5-ňacoB b npHcyTCTBHH BFj/EtjO b KanecTBe KaTanH3aTOpah Tax nonyneHHbifí 2-n3o6yTH.noKCHMeTH.n-l .4.6-TpnoKca-cnnpo- [4.4] -ηοηθη ποπη-MepH3yeTCH ηπη ο^ηη ηπη c. floneň no 30» MonbHbix npoiíeHTOB pacTBOpeHHoro bΗΘΜ 2,2-6hC~(1 ,4.6-TpHOKCa-cnHpO-[4.4^-ΗΟΗ3Η-2-ΜβΤΗηθΚΟΗφβΗΗη)-ΠρθΠ3Η3 BnpHcyTCTBHH Et^O^SbClg b KojmecŤBe c 1 Bec.% po 3 Bec.% OTHOCHTenbHO ko-nHnecTBa οπΗροορτοΒφκρβ πρκ 80 po 100 C b TeneHHe 6 flo 8 nacOB,
AHHOTan,KH
Cnoco6 nonyneHHB cnoxHbix ποπηβΦηροβ c ManbíM HanpHaceHHeM. Uenb Η3θ6ρετεΗΗΗ -TexHHnecKH Hcnonb3OBaTb oneHb Manoe oCteMKoe cxaTHe επΗροορτοοφΗροΒ flnanonyneHHn cno«Hbix ποηΗ3φκροΒ c ManbW HanpH»eHHeM H36eraa κεηοετετκοΒ πρκH3BecTHbJX flO CHX ΠΟρ ΠΟΠΗΜερΗ33Ι(ΗΗΧ 0ΠΗρθθρΤΟ3φΗρθΒ. 3aflana - yKa3aTb cnoco6, npH noMonm κοτοροΓ.ο bO3mo®ho no/jBepraTb nonHMepn-3auHH προοτο MaHHnynHpyeMbie, CTa6HnbHbie h nerKO nonynaeMbie οπΗροορτο3φΗρωo6pa3yn cnoxHbie ποηκΒφΗρΜ c ManbíM HanpaxeHHeM pemaeTca τβΜ, ητο 2-H3o6yTHn-OKCHMeTHn-1,4.6-TprtOKca-criHpo-[4.4]-HOHaH, nonyneHHbiň H3 6yTHponaKTOHa hH3o6yTHnrnHu;HflOBoro Βφκρε, nonHMěpH3yeTCH ηπη ο«ηη ηπη, c floneň po 30 μοπβ-HblX npOHeHTÓB 2,2-6hC-(1 .4.6-TpHOKCa-cnHpO- [4.4]-ΗΟΗέΗ-2-ΜβΤΗΠΟΚΟΗφβΗΗπ)-nponaHa b npHcyTCTBHH EtsO+SbClg. IIonyneHHbie cornacHO η3ο6ρθτθηηκ> cnoxHbieΠΟΠΗ3ΦΗΡΜ MOryT HHňTH ΠρΗΜΘΗβΗΗβ B OIJTHHeCKOň ΠρθΜΜΙΠΠ6ΗΗΟΟΤΗ B KaHeCTBeonranecKH npo3panHbix nojiHMepHbix φορΜΟΒΟΗΗΗΧ MaTepHHjiOB, npeuH3HOHHoro Kneaηπη b Kanec Tne cTpyKTypHbix KneeB. IIpH3HaHO Η3θ6ρβΤβΗΗβΜ ΠΟ pe3ynhTaTaM 3KCnepTH3Wt OCymeCTBneHHOň BeflOMCTBOMno p;enaM Η3θ6ρβτεΗΗϋ h naTeHTOB PflP. 248293
Claims (1)
- 248 293 P R E D M S T VYNÁLEZU Způsob výroby polyesterů s malým pnutím· ze spiroorto-esterů, vyznačující se tím, že se nechá reagovat butyro-lakton a izobutylglycidový ester v molárním poměru 1 : 1až 2 : 1 v tetrachlormetanu jako rozpouštědle, při 30 °Cpo dobu 5 hodin v přítomnosti BP^ . Et£0 jako katalyzátoru,a vzniklý 2-izobutyloximetyl-l,4,6-trioxa-spiro-/4,4/-nonan se polymeruje bu3 samotný nebo s podílem do 30 % mol.v něm rozpuštěného 2,2-bis-/l,4,6-trioxa-spiro-/4,4/ -nonan-2-metyloxifenyl/propanu v přítomnosti Et^O+SbCl^“v množství 1 % hmot. až 3 % hmot. vztaženo k spiroortoes-teru, při 80 až 100 °C po dobu 6 až 8 hodin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD24033182A DD208468A3 (de) | 1982-06-01 | 1982-06-01 | Verfahren zur herstellung spannungsarmer polyesterether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS353083A1 CS353083A1 (en) | 1985-06-13 |
| CS248293B1 true CS248293B1 (en) | 1987-02-12 |
Family
ID=5538945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS833530A CS248293B1 (en) | 1982-06-01 | 1983-05-19 | Method of polyester production with small stress |
Country Status (4)
| Country | Link |
|---|---|
| BG (1) | BG42587A1 (cs) |
| CS (1) | CS248293B1 (cs) |
| DD (1) | DD208468A3 (cs) |
| SU (1) | SU1451144A1 (cs) |
-
1982
- 1982-06-01 DD DD24033182A patent/DD208468A3/de not_active IP Right Cessation
-
1983
- 1983-04-26 SU SU837772942A patent/SU1451144A1/ru active
- 1983-05-06 BG BG6086183A patent/BG42587A1/xx unknown
- 1983-05-19 CS CS833530A patent/CS248293B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS353083A1 (en) | 1985-06-13 |
| DD208468A3 (de) | 1984-05-02 |
| BG42587A1 (en) | 1988-01-15 |
| SU1451144A1 (ru) | 1989-01-15 |
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