CS195255B2 - Process for preparing alpha-anilinocarbonitriles - Google Patents
Process for preparing alpha-anilinocarbonitriles Download PDFInfo
- Publication number
- CS195255B2 CS195255B2 CS289572A CS289572A CS195255B2 CS 195255 B2 CS195255 B2 CS 195255B2 CS 289572 A CS289572 A CS 289572A CS 289572 A CS289572 A CS 289572A CS 195255 B2 CS195255 B2 CS 195255B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- mol
- dichloroanilino
- alpha
- hydrogen
- hydrogen chloride
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 29
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 13
- 150000002825 nitriles Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- -1 aniline compound Chemical class 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 10
- CDADMVLQUGFJNY-UHFFFAOYSA-N 2-(3,4-dichloroanilino)propanenitrile Chemical compound N#CC(C)NC1=CC=C(Cl)C(Cl)=C1 CDADMVLQUGFJNY-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- ACMJJQYSPUPMPN-UHFFFAOYSA-N 4-chloro-3-fluoroaniline Chemical compound NC1=CC=C(Cl)C(F)=C1 ACMJJQYSPUPMPN-UHFFFAOYSA-N 0.000 claims description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 3
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 238000002474 experimental method Methods 0.000 claims 5
- 238000010438 heat treatment Methods 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- TUFYEVMTXRPQQK-UHFFFAOYSA-N ethyl 2-(3,4-dichloroanilino)propanoate Chemical compound CCOC(=O)C(C)NC1=CC=C(Cl)C(Cl)=C1 TUFYEVMTXRPQQK-UHFFFAOYSA-N 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- 238000005191 phase separation Methods 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- SUWRMAZHFSUJCB-UHFFFAOYSA-N 2-(3,4-dichloroanilino)propanoic acid Chemical compound OC(=O)C(C)NC1=CC=C(Cl)C(Cl)=C1 SUWRMAZHFSUJCB-UHFFFAOYSA-N 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 238000005242 forging Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 claims 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 239000012264 purified product Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Substances Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract description 5
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract description 4
- 239000012429 reaction media Substances 0.000 abstract description 4
- KMWRISRTGYELKS-UHFFFAOYSA-N 2-(4-fluoroanilino)propanenitrile Chemical compound N#CC(C)NC1=CC=C(F)C=C1 KMWRISRTGYELKS-UHFFFAOYSA-N 0.000 abstract description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract description 3
- SKBGHSYTMQEDCY-UHFFFAOYSA-N 2-(4-chloro-3-fluoroanilino)propanenitrile Chemical compound N#CC(C)NC1=CC=C(Cl)C(F)=C1 SKBGHSYTMQEDCY-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000075 primary alcohol group Chemical group 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- CPVVCMJTNOXQBI-UHFFFAOYSA-N 2-(4-chloroanilino)propanenitrile Chemical compound N#CC(C)NC1=CC=C(Cl)C=C1 CPVVCMJTNOXQBI-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- QAGSSWOCKAKQCQ-UHFFFAOYSA-N ClC1(CC=C(NC(C#N)C)C=C1)F Chemical compound ClC1(CC=C(NC(C#N)C)C=C1)F QAGSSWOCKAKQCQ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1241071 | 1971-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195255B2 true CS195255B2 (en) | 1980-01-31 |
Family
ID=10004092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS289572A CS195255B2 (en) | 1971-04-30 | 1972-04-28 | Process for preparing alpha-anilinocarbonitriles |
Country Status (18)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1547758A (en) * | 1975-07-29 | 1979-06-27 | Shell Int Research | Herbicidal composition |
| GB1577662A (en) * | 1976-05-08 | 1980-10-29 | Basf Ag | Manufacture of glycinonitriles |
| US4318920A (en) * | 1979-02-08 | 1982-03-09 | Abbott Laboratories | Ovicides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE151538C (enrdf_load_stackoverflow) * | ||||
| NL136594C (enrdf_load_stackoverflow) * | 1965-10-22 | |||
| US3463805A (en) * | 1967-05-08 | 1969-08-26 | Grace W R & Co | Production of aminonitriles under adiabatic conditions |
| GB1307978A (en) * | 1969-02-28 | 1973-02-21 | Wellcome Found | Amidines processes for their preparation and pharmaceutical compo sitions incorporating the same |
-
1971
- 1971-04-30 GB GB1327294D patent/GB1327294A/en not_active Expired
-
1972
- 1972-04-25 BE BE782595A patent/BE782595A/nl not_active IP Right Cessation
- 1972-04-27 NL NL7205688A patent/NL175173C/xx not_active IP Right Cessation
- 1972-04-27 DK DK212772A patent/DK153472C/da not_active IP Right Cessation
- 1972-04-28 DE DE19722221109 patent/DE2221109C2/de not_active Expired
- 1972-04-28 PL PL15504972A patent/PL83652B1/pl unknown
- 1972-04-28 CH CH639572A patent/CH589049A5/xx not_active IP Right Cessation
- 1972-04-28 ES ES402224A patent/ES402224A1/es not_active Expired
- 1972-04-28 FR FR7215325A patent/FR2139847B1/fr not_active Expired
- 1972-04-28 CA CA140,875A patent/CA982141A/en not_active Expired
- 1972-04-28 JP JP47042319A patent/JPS5749537B1/ja active Pending
- 1972-04-28 IT IT2369672A patent/IT953845B/it active
- 1972-04-28 RO RO7073672A patent/RO62750A/ro unknown
- 1972-04-28 CS CS289572A patent/CS195255B2/cs unknown
- 1972-04-28 SU SU1778332A patent/SU461492A3/ru active
- 1972-04-28 HU HUSE001623 patent/HU164835B/hu not_active IP Right Cessation
- 1972-04-28 DD DD16264872A patent/DD101889A5/xx unknown
- 1972-05-03 YU YU115772A patent/YU39269B/xx unknown
-
1980
- 1980-07-30 JP JP10378180A patent/JPS5639057A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL175173B (nl) | 1984-05-01 |
| GB1327294A (en) | 1973-08-22 |
| DE2221109C2 (de) | 1983-10-06 |
| IT953845B (it) | 1973-08-10 |
| FR2139847A1 (enrdf_load_stackoverflow) | 1973-01-12 |
| YU39269B (en) | 1984-10-31 |
| CA982141A (en) | 1976-01-20 |
| FR2139847B1 (enrdf_load_stackoverflow) | 1973-12-07 |
| DD101889A5 (enrdf_load_stackoverflow) | 1973-11-20 |
| PL83652B1 (enrdf_load_stackoverflow) | 1975-12-31 |
| NL175173C (nl) | 1984-10-01 |
| YU115772A (en) | 1982-05-31 |
| SU461492A3 (ru) | 1975-02-25 |
| JPS5639057A (en) | 1981-04-14 |
| HU164835B (enrdf_load_stackoverflow) | 1974-04-11 |
| RO62750A (fr) | 1977-10-15 |
| AU4168072A (en) | 1973-11-01 |
| BE782595A (nl) | 1972-10-25 |
| NL7205688A (enrdf_load_stackoverflow) | 1972-11-01 |
| ES402224A1 (es) | 1976-01-01 |
| CH589049A5 (enrdf_load_stackoverflow) | 1977-06-30 |
| DK153472B (da) | 1988-07-18 |
| DE2221109A1 (de) | 1972-11-16 |
| JPS5736274B2 (enrdf_load_stackoverflow) | 1982-08-03 |
| DK153472C (da) | 1988-11-21 |
| JPS5749537B1 (enrdf_load_stackoverflow) | 1982-10-22 |
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