PL68924B1 - - Google Patents
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- PL68924B1 PL68924B1 PL13479769A PL13479769A PL68924B1 PL 68924 B1 PL68924 B1 PL 68924B1 PL 13479769 A PL13479769 A PL 13479769A PL 13479769 A PL13479769 A PL 13479769A PL 68924 B1 PL68924 B1 PL 68924B1
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002497 iodine compounds Chemical class 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002892 organic cations Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- -1 potassium diethylphosphonothionate Chemical compound 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YRYAOFXWGMHWQO-UHFFFAOYSA-N COP(=O)(O)S(=O)OC Chemical compound COP(=O)(O)S(=O)OC YRYAOFXWGMHWQO-UHFFFAOYSA-N 0.000 description 1
- XXNRHOAJIUSMOQ-UHFFFAOYSA-N Methylphosphonothioic acid o-ethyl ester Chemical compound CCOP(C)(O)=S XXNRHOAJIUSMOQ-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AIJQQTBLBLBZDI-UHFFFAOYSA-M ethoxy-ethyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP([O-])(=S)CC AIJQQTBLBLBZDI-UHFFFAOYSA-M 0.000 description 1
- AYUMCDSXPRPYLX-UHFFFAOYSA-N ethyl n-(2-chloroacetyl)-n-methylcarbamate Chemical compound CCOC(=O)N(C)C(=O)CCl AYUMCDSXPRPYLX-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Benzenowy roztwór przemyto 2 n roz¬ tworem weglanu sodowego (20 ml), nastepnie 1% roztworem chlorku sodowego (20 ml), suszono nad bezwodnym siarczanem sodowym i benzen odde¬ stylowano pod zmniejszonym cisnieniem w tem¬ peraturze 50—60°C. Pozostaly olej wazyl 33,2* g (94% wydajnosci) i destylowal w temperaturze 140°C pod cisnieniem 0,3 mm Hg, n " 1,4985 (Zna¬ leziono: S — 11,3% dla C9H18NO5PS zawartosc S — 11,3%).Przyklad XIII. Otrzymywanie O-etylo-ety¬ lofosfonotionianu (N-etoksy-karbonylo-N-metylo- karbamylometylowego).Ten zwiazek, wytworzony metoda wedlug przy¬ kladu I z ta róznica, ze uzyto dwuetylofosfonotio- nianu potasowego i N-chloroacetylo-N-metylokar- baminianu etylowego, destylowal w temperaturze 142°C pod cisnieniem 0,3 mm Hg, n ^ 1,4930 (Zna¬ leziono: S — 10,76% dla C10H20NO5PS zawartosc S wynosi 10,77%).Nastepujace zwiazki wytworzono zgodnie ze spo¬ sobem wedlug przykladu I, uzywajac odpowied* nich materialów wyjsciowych:68 924 23 24 Przyklad nr 1 XIV XV XVI XVII XVIII XIX XX XXI XXII • XXIII XXIV xxv XXVI Zwiazek 1 2 O-metylo-metylo-fosfono- merkaptotionian S-(N-meto- ksybarkonylo-N-etylo-kar- bamylometylowy) O-metylo-metylo-fosfonotio- nian N-metoksykarbonylo- N-etylokarbamylometylowy O-metylo-metylofosfonomer- kaptotionian S-(N-etoksy- karbonylo-N-metylokarba- mylometylowy O-propylo-etylofosfono-mer- kaptotionian- S-(N-metoksy- karbonylo-N-metylokarba- mylometylowy) O-propyloetylo-fosfonomer- kaptotionian S-(N-etoksy- karbonylo-N-metylokarba- mylometylowy) O-butyloetylofosfonomer- kaptotionian S-(N-metoksy- karbonylo-N-metylokarba- mylometylowy O-butyloetylo-fosfonomer- kaptotionian S-(N-etoksy- karbonylo-N-metylo-karba- mylometylowy) O-alliloetylofosfonomerkap- totionian S-(N-metoksykar- bonylo-N-metylo-karbamy- lometylowy) O-alliloetylofosfonomerkap- totionian S-(N-etoksykarbo- nylo-N-metylo-karbamylo- metylowy) O-metylo-metylofosfonotio- nian N-metoksykarbonylo- karbamylometylowy O-2-chloroacetylo-etylofos- fonomerkaptotionian- S-(N- -metoksykarbonylo-N-mety- lo-karbamylometylowy) O-2-chloroetylo-etylofosf-ono- merkaptotionian S-(N-eto- ksykarbonylo-N-metylokar- bamylometylowy O-metylo-metylofosfonotio- nian N-metoksybarbonylo- -karbamylometylowy » ' "' lin 1 ' • *i ' ¦ ¦ Temperatura wrzenia/ /mm Hg 1 3 139—140°/0,3 135—13670,3 139—140°/0,2 132—370,3 132—2°/0,15 160—170,3 161—2°/0,2 158—970,25 161—2°/0,2 Temperatura topnienia 144—6° '.. nD 1 4 1.5385 1.4999 1.5368 1.5305 1.5221 1.5256 1.5188 1.5418 i 1.5319 Biale slupki z ace¬ tonu 1.5461 1.5329 1.5039 czerwo¬ ny olej Wzór cza¬ steczkowy 5 C8Hi6N04PS2 CaH16N05PS C8Hi6N04PS2 C10H20NO4PS2 C11H22NO4PS CnH22N04PS2 Ci2H24N04PS2 C6H12N05PS C8Hi6N05PS Wyniki analizy Znaleziono P 1 S 1 « 1 f 10,0 12.90 11.7 22,65 12.00 22,25 20,45 19,43 19,79 18,70 19.8 19.8 18.3 Wyliczono P 1 8 10,0 12,86 11.5 1 S 1 9 22,46 1,90 22,46 20,45 19,57 19,57 18,77 19,7 19.2 18.4 '68 924 ** cd. tablicy 1 1 XXVII XXVIII XXXIX XXX XXXI XXXII XXXIII XXXIV xxxv XXXVI XXXVII XXXVIII XXXIX 1 2 O-etylometylofosfonotionian (N-metoksykarkonylo-N- metylokarbamylometylowy) O-propylometylofosfonomer- kaptotionian S-(N-metoksy- karbonylokarbamylomety- lowy) O-propylometylofosfonomer- kaptotionian S-(N-metoksy- karbonylo-N-metylokarba- mylometylowy) 1 O-metylo-metylofosfonomer- kaptotionian S-(N-metoksy- karbonylo-N-metylokarba- mylometylowy) O-propylo-propylofosfono- merkaptotionian S-(N-meto- ksykarbonylo- N-metylokar- bamylometylowy) O-butylo-butylofosfonomer- kaptotionian S-(N-metoksy karbonylo-N-metylo-karba- mylometylowy) O-etylo-metylofosfonomer- kaptotionian S-(N-alliloksy- karbonylo-N-metylokarba- mylometylowy) O-metylo-etylofosfonomer- kaptotionian Sn(N-heksylo- ksykarbonylo-N-metylokar- bamylometylowy) O-metylofenylofosfonomer- kaptotionian S-(N-metoksy- karbonylokarbamylomety- lowy) O-metylofenylofosfonomer- kaptotionian S-(N-etyksykar- bonylokarbamylometylowy) O-metylofenyTofosfonomer- kaptotionian S-(N-metoksy- karbonylo N-metylokarba- mylometylowy O-metylofenylofosfonomer- kaptotionian S-(N-etoksykar- bonylo-N-metylokarbamylo- metylowy) O-2-etoksyetylo-etylofosfo- nomerkaptotionian S-(N-eto- ksykarbonylo-N-metylokar- bamylometylowy) 1 3 134—135°/0,3 Temperatura topnienia 75—76° bla¬ do brunatne igly z pro- pan-2-olu 140—141°/0,25 15470,4 152°/0,05 158—15970,3 178—179,570,3 X 1 4 1.4998 [ 1.5350 1.5360 1.5239 brunat¬ ny olej 1.5205 1.5349 1.5124 1.6040 1.5895 1.5915 zólto- brunat- ny olej 1.3742 brunat¬ ny olej 1.5218 1 5 CsHisNOsPS CsHieNOtPS C9H18N04PS2 C9H18N04PS2 CnHzaNOiPSa C13H26NO4PS2 C11H20NO4PS2 Cl4H2«N04PS2 CuHmNCUPSz C12H16NO4PS2 Ci2Hi6N04PS2 Ci3H18N04PS2 Ci2H24N05PS2 1 1 6 9.4. 8.2 9.7 9.3 9.4. 9.0 1 7 11.9 23.0 22,0 21.1 19.3 17.7 18.3 1 8 9.5 8.4. 9.7 9.3 9.3 8.9 1 9 T 11.9 21.5 21,4 21.4 19.6 16.0 17JXL XLI XLII XLIII XLIV XLV XLVI XLVIII XLVIII XLIX LI 27 O-2-etoksyetylo-etylofosfono- merkaptotionian S-(N-meto- ksykarbonylo-N-metylokar- -bamylometylowy) O-izopropylo-izopropylofos- fonomerkaptotionian S-(N- metoksykarbonylo-N-mety- lokarbamylometylowy O-IIrz.-butyknll-rz-butylo- fosfonomerkaptotionian S- -(N-metoksykarbonylo-N- -metylokarbamylometylowy) O-etylometylofosfonomer- kaptotionian S-(N-metoksy- karbonylokarbamylometylo- wy) O-propylometylofosfonotio- nian N-metoksybarbonylo- -N-metylokarbamylometylo- wy) O-butylo-butylofosfonomer- kaptotionian S-(N-metoksy- karbonylokarbamylomety- lowy) O-propylo-propylofosfono- merkaptotionian S-(N-meto- ksykarbonylo-karbamylo- metylowy) O-butylo-II-rz-butylofosfo- nomerkaptotionian S-(N-me- toksykarbonylo-N-metylo- karbamylometylowy) O-izopropylo-propylofosfono- merkaptotionian S-(N-meto- ksykarbonylo-N-metylokar- bamylometylowy) O-propyloizopropylofosfono- merkaptotionian S-(N-meto- ksykarbonylo-N-metylokar- bamylometylowy) O-propyloizopropylofosfono- tionian N-metoksykarbony- lo-N-metylokarbamylomety- lowy O-pr.opyloizopropylofosfo- notionian N-etoksykarbony- lokarbamylometylowy I 68 924 28 149—15070,3 Temperatura topnienia 88—88,5 bia¬ le slupki z propan-2-olu 140—14270,3 Temperatura topnienia 41—45° biale igly z eteru naftowego (t. wrz. 40—60) Temp. topn. 73—75° biale plytkli z eteru naftowego (t.wrz. 40— 60) 16070,5 mm 1.5289 1.5251 1.5205 1.4957 1.5206 1.5295 1.5298 zólty olej 1.4936 zólty olej 1.4928 poma¬ ranczo¬ wy olej CiiH22N05PS2 CnHzzNC^PSz Ci3H26N04PS2 C7HHNO4PS2 C9H18N05PS C12H24N04PS2 C10H20NO4PS2 Ci3H26N04PS2 CiiH22N04PS2 CnH22N04PS2 CnH22N05PS; CnH22N05PS 18.8 9.8 8.3 10,3 10.0 24.0 11.3 18.5 21.6 17.6 20.5 20.2 c.d. tablicy 8 9 18.7 9.5 8.7 23.6 11.3 18.8 21.1 18.0 19.6 19.6 10.0 10.068 924 29 30 PL PL
Claims (3)
1. Zastrzezenie patentowe baminian o ogólnym wzorze 3 w którym R2 i R* maja wyzej podane znaczenie, a Hal oznacza atom Sposób wytwarzania nowych zwiazków fosfono- chloru, bromu lub jodu, poddaje sie w reakcji al- wych o wlasciwosciach szkodnikobójczych o ogól- bo z podstawionym kwasem fosfoniowym o ogól¬ nym wzorze 1," w którym R oznacza nizsza grupe 5 nym wzorze 2, w którym R, Ri X i Y maja wy- alkilowa lub grupe fenylowa, Ri oznacza nizsza zej podane znaczeni a Q oznacza atom wod grupe alkilowa lub nizsza grupe alkenylowa lub metal ^ amon lub kation organiczny w nizsza grupe alkilowa podstawiona atomem chlo- __ ,. __ A , , , _ 11 1 1 ™ obecnosci substancji wiazacej kwas w przypad- rowca lub nizsza grupa alkoksylowa, R2 oznacza , atom wodoru lub nizsza grupe alkilowa, R« ozna- 10 kU' gdy Q °ZnaCZa *tom WOdorU; alb° Ze ZWiaz" cza grupe alkilowa o 1-6 atomach wegla lub kiem ° °^ólnym wzorz* 4, w którym R ma wyzej nizsza grupe alkenylowa a X i Y, które moga byc podane znaczenie w obecnosci substancji wiaza- takie same lub rózne, i oznaczaja atomy tlenu lub cej kwas i alkoholu o wzorze RiOH, w którym siarki, znamienny tym, ze N-halogenoacetylo-kar- R1 ma wyzej podane znaczenie. ERRATA W tablicy 1, 'przyklad nr XX^7TII w rubryce 2 jest: 50 ppm powinno byc: 250 pipm Pod taihlica 3 jest: 2) -dwumetylo S-/NHmetylakarbainoilometylo/ fosfoiromerkaptototioinian 3) S-[l,2Hdwu/e1x)iksykarbony(lo/e1y!lo] dwume- tylofosforemericaptioniian powinno byc:
2. ) dwumetylo S-/N-metylokanbamoilometylo/ fos£oax)imerkapitotioinian
3. ) S-[l,2-dwu/e1xlffiyikjarbonylo/eJtylo] dwume- tylofosforemerkap1xtioniian Lam 22, wiersz 39 jest: (benzynie powinno byc: benzenie W zestawiieniu, lam 23, rubryka 2, przyklad XIV, wiersz 3 jest: ksybarkonylo-N-^etyilo^kar- powinno byc: ksykarbonylo-N-etylo-kar- W zestawieniu, lam 23, mibryika 2, przyklad XXVI, wiersz 2 jest: nian NHmetoksybarbonylo- powinno byc: oian Nnmetoiksykiarlbonylo- W zestawieniu, lam 25, rubryka 2, przyklad XXVII, wiersz 2 - jest: /N-metoksykarkionylo-N- powinno byc: /N-metoksykarboinylo-N- W zestawieniu, lam 27, rubryka 2, przyklad XLIV, wiersz 2 jest: ndan N-metoksytoaribonyiLo- powinno byc: nian N-metaksykarbonylo-KI. 12o,26/01 68924 MKP C07f 9/40 OR1 1 2 3 X= P—Y—CH2.CO.ND .C02C3 R WZOD 1 OR" I X=P —Y—Q I R WZOP 2 Hal.CH2.CO.NR2C02R3 WZÓR 3 S II R—P-S I I S-P-R II S WZÓR AKI. 12o,26/01 68924 MKP C07f 9/40 OCHo I 3 S=p_SK + a£H2.CO.N(CH3).C02.CH3 CH3 0CH3 S=P-S.CH2.CO.N(CH3).C02.CH3 CH3 SCHEMAT 1 CH--P-S 3 I I S- P-CH3+ CH3OH+Na2C03+a.CH2.CO.Nfc:H3,).C02.CH3 S OCH, S= P-S.CH2.CO.N(CH3).C02.CH3 CH3 SCHEMAT 2KI. 12o,26/01 68924 MKP C07f 9/40 OCH* I S=P-SK + CICH2.CQN(CH3').C02.CH3 OCH. J 3 * s=p-s.ch2.co.n(ch3Vco2.ch3 C2H5 SCHEMAT 3 OCH* I S=P-SK + a.CH2.CO.N(CH3).C02.C2H5 C2H5 OCH, I S=P-S.CH2.CO.N(CH3).C02.C2H5 SCHEMAT AKI. 12o,26/01 68 924 MKP C07f 9/40 OC2H5 s=p-sk + ci.ch2.co.n(ch3Vco2.c2h5 CH3 OC2H5 ^ S=P-S.CH2.CQN(CH3).C02.C2H5 CH3 SCHEMAT 5 OC2H5 I S= P- SK+Cl.CH2.CO.N(CH3).C02.C2H5 C2H5 OC2H5 S=P-S.CH2.CQN(CH^C09.C,H -2H5 SCHEMAT 6KI. 12o,26/01 68924 MKP C07f 9/40 OCH2H5 S=p-SK + a.CH2.CaN(C2H5).C02.C2H5 C2H5 OCohU I ?S-P-S.CH2.CO.N(C^;].C0fe.C2H5 C2H5 SCHEMAT 7 OCH. I S=p-SK+ CLCH2.CO.NH.C02.CH3 CH3 OCH3 ¦*- S=P-S.CH2.CO.NH.C02.CH3 CH3 SCHEMAT 8 Zaklady Typograficzne, zam. 1014/73 — 105 egz. Cena 10 zl PL PL
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL13479769A PL68924B1 (pl) | 1969-07-14 | 1969-07-14 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL13479769A PL68924B1 (pl) | 1969-07-14 | 1969-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL68924B1 true PL68924B1 (pl) | 1973-02-28 |
Family
ID=19950714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL13479769A PL68924B1 (pl) | 1969-07-14 | 1969-07-14 |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL68924B1 (pl) |
-
1969
- 1969-07-14 PL PL13479769A patent/PL68924B1/pl unknown
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