DE2422955B2 - Verfahren zur herstellung von dithiocarbamidsauren ammoniumsalzen - Google Patents
Verfahren zur herstellung von dithiocarbamidsauren ammoniumsalzenInfo
- Publication number
- DE2422955B2 DE2422955B2 DE19742422955 DE2422955A DE2422955B2 DE 2422955 B2 DE2422955 B2 DE 2422955B2 DE 19742422955 DE19742422955 DE 19742422955 DE 2422955 A DE2422955 A DE 2422955A DE 2422955 B2 DE2422955 B2 DE 2422955B2
- Authority
- DE
- Germany
- Prior art keywords
- ammonium salts
- bis
- sulfur
- preparation
- dithiocarbamic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 ACIDS AMMONIUM SALTS Chemical class 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 239000011593 sulfur Substances 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- LRKYLKBLUJXTFL-UHFFFAOYSA-N 1-(piperidin-1-ylmethyl)piperidine Chemical compound C1CCCCN1CN1CCCCC1 LRKYLKBLUJXTFL-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- KQISQNCCCASSDX-UHFFFAOYSA-N 1-(pyrrolidin-1-ylmethyl)pyrrolidine Chemical compound C1CCCN1CN1CCCC1 KQISQNCCCASSDX-UHFFFAOYSA-N 0.000 description 2
- MIFZZKZNMWTHJK-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)morpholine Chemical compound C1COCCN1CN1CCOCC1 MIFZZKZNMWTHJK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AABDVYQCZLGQGH-UHFFFAOYSA-N 1-(azepan-1-ylmethyl)azepane Chemical compound C1CCCCCN1CN1CCCCCC1 AABDVYQCZLGQGH-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UNEXJVCWJSHFNN-UHFFFAOYSA-N n,n,n',n'-tetraethylmethanediamine Chemical compound CCN(CC)CN(CC)CC UNEXJVCWJSHFNN-UHFFFAOYSA-N 0.000 description 1
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/21—Radicals derived from sulfur analogues of carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742422955 DE2422955B2 (de) | 1974-05-11 | 1974-05-11 | Verfahren zur herstellung von dithiocarbamidsauren ammoniumsalzen |
| IN840/CAL/75A IN138713B (enExample) | 1974-05-11 | 1975-04-26 | |
| GB1895275A GB1482825A (en) | 1974-05-11 | 1975-05-06 | Process for the production of ammonium salts of dithiocarbamic acid |
| BE156189A BE828883A (fr) | 1974-05-11 | 1975-05-09 | Procede de preparation de dithiocarbamates d'ammonium |
| JP50054482A JPS5224008B2 (enExample) | 1974-05-11 | 1975-05-09 | |
| IE104575A IE41121B1 (en) | 1974-05-11 | 1975-05-09 | A process for the production of ammonium salts of dithiocarbamic acids |
| BR7503668A BR7502884A (pt) | 1974-05-11 | 1975-05-09 | Processo para a preparacao de sais de amonio acidos ditiocarbamidicos |
| FR7514572A FR2270243B1 (enExample) | 1974-05-11 | 1975-05-09 | |
| NL7505500A NL7505500A (nl) | 1974-05-11 | 1975-05-09 | Werkwijze voor de bereiding van dithiocarbami- dezure ammoniumzouten. |
| LU72434A LU72434A1 (enExample) | 1974-05-11 | 1975-05-09 | |
| DK205775A DK135039C (da) | 1974-05-11 | 1975-05-09 | Fremgangsmade til fremstilling af dithiocarbamidsure ammoniumsalte |
| IT4950775A IT1035666B (it) | 1974-05-11 | 1975-05-09 | Procedimento per la produzione di sali d ammonio ditiocarbammeti |
| US05/833,629 US4150022A (en) | 1974-05-11 | 1977-09-15 | Process for the production of ammonium salts of dithiocarbamic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742422955 DE2422955B2 (de) | 1974-05-11 | 1974-05-11 | Verfahren zur herstellung von dithiocarbamidsauren ammoniumsalzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2422955A1 DE2422955A1 (de) | 1975-11-20 |
| DE2422955B2 true DE2422955B2 (de) | 1976-06-10 |
Family
ID=5915319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742422955 Granted DE2422955B2 (de) | 1974-05-11 | 1974-05-11 | Verfahren zur herstellung von dithiocarbamidsauren ammoniumsalzen |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5224008B2 (enExample) |
| BE (1) | BE828883A (enExample) |
| BR (1) | BR7502884A (enExample) |
| DE (1) | DE2422955B2 (enExample) |
| DK (1) | DK135039C (enExample) |
| FR (1) | FR2270243B1 (enExample) |
| GB (1) | GB1482825A (enExample) |
| IE (1) | IE41121B1 (enExample) |
| IN (1) | IN138713B (enExample) |
| IT (1) | IT1035666B (enExample) |
| LU (1) | LU72434A1 (enExample) |
| NL (1) | NL7505500A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2534654C (en) | 2003-07-31 | 2013-01-08 | C. Rasmussen Martin | System and method for moving objects |
-
1974
- 1974-05-11 DE DE19742422955 patent/DE2422955B2/de active Granted
-
1975
- 1975-04-26 IN IN840/CAL/75A patent/IN138713B/en unknown
- 1975-05-06 GB GB1895275A patent/GB1482825A/en not_active Expired
- 1975-05-09 BE BE156189A patent/BE828883A/xx unknown
- 1975-05-09 FR FR7514572A patent/FR2270243B1/fr not_active Expired
- 1975-05-09 NL NL7505500A patent/NL7505500A/xx unknown
- 1975-05-09 BR BR7503668A patent/BR7502884A/pt unknown
- 1975-05-09 IT IT4950775A patent/IT1035666B/it active
- 1975-05-09 DK DK205775A patent/DK135039C/da active
- 1975-05-09 IE IE104575A patent/IE41121B1/xx unknown
- 1975-05-09 JP JP50054482A patent/JPS5224008B2/ja not_active Expired
- 1975-05-09 LU LU72434A patent/LU72434A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN138713B (enExample) | 1976-03-20 |
| JPS50154211A (enExample) | 1975-12-12 |
| DE2422955A1 (de) | 1975-11-20 |
| IE41121B1 (en) | 1979-10-24 |
| FR2270243A1 (enExample) | 1975-12-05 |
| JPS5224008B2 (enExample) | 1977-06-28 |
| LU72434A1 (enExample) | 1976-03-17 |
| BR7502884A (pt) | 1976-03-23 |
| DK205775A (da) | 1975-11-12 |
| BE828883A (fr) | 1975-11-10 |
| DK135039C (da) | 1977-08-01 |
| IT1035666B (it) | 1979-10-20 |
| IE41121L (en) | 1975-11-11 |
| FR2270243B1 (enExample) | 1980-05-16 |
| NL7505500A (nl) | 1975-11-13 |
| DK135039B (da) | 1977-02-28 |
| GB1482825A (en) | 1977-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |