NO137591B - APPLIANCE FOR BIOLOGICAL TREATMENT OF WASTEWATER - Google Patents
APPLIANCE FOR BIOLOGICAL TREATMENT OF WASTEWATER Download PDFInfo
- Publication number
- NO137591B NO137591B NO4380/73A NO438073A NO137591B NO 137591 B NO137591 B NO 137591B NO 4380/73 A NO4380/73 A NO 4380/73A NO 438073 A NO438073 A NO 438073A NO 137591 B NO137591 B NO 137591B
- Authority
- NO
- Norway
- Prior art keywords
- chloride
- wastewater
- appliance
- biological treatment
- chloroaniline
- Prior art date
Links
- 239000002351 wastewater Substances 0.000 title 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- HUSSZVNDYXDUML-UHFFFAOYSA-N NC(C=CC=C1S(Cl)(=O)=O)=C1S(Cl)(=O)=O Chemical class NC(C=CC=C1S(Cl)(=O)=O)=C1S(Cl)(=O)=O HUSSZVNDYXDUML-UHFFFAOYSA-N 0.000 claims description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
- 150000008045 alkali metal halides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WFGYSQDPURFIFL-UHFFFAOYSA-N 3-chloro-n-methylaniline Chemical compound CNC1=CC=CC(Cl)=C1 WFGYSQDPURFIFL-UHFFFAOYSA-N 0.000 description 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
- YIZXGHNDQUYDDF-UHFFFAOYSA-N 4-amino-6-chlorobenzene-1,3-disulfonyl chloride Chemical compound NC1=CC(Cl)=C(S(Cl)(=O)=O)C=C1S(Cl)(=O)=O YIZXGHNDQUYDDF-UHFFFAOYSA-N 0.000 description 1
- SSMBCLXOFGMJEZ-UHFFFAOYSA-N 4-amino-6-fluorobenzene-1,3-disulfonyl chloride Chemical compound NC1=CC(F)=C(S(Cl)(=O)=O)C=C1S(Cl)(=O)=O SSMBCLXOFGMJEZ-UHFFFAOYSA-N 0.000 description 1
- XXPRZZAHJDMBSP-UHFFFAOYSA-N 4-amino-6-methoxybenzene-1,3-disulfonyl chloride Chemical compound COC1=C(C=C(C(N)=C1)S(=O)(=O)Cl)S(=O)(=O)Cl XXPRZZAHJDMBSP-UHFFFAOYSA-N 0.000 description 1
- VPXCXBHLKDPWQV-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C(S(O)(=O)=O)=C1 VPXCXBHLKDPWQV-UHFFFAOYSA-N 0.000 description 1
- HMXFVSHKRGAWON-UHFFFAOYSA-N ClC=1C=C(C(N)=CC=1S(=O)(=O)Cl)S(=O)(=O)Cl Chemical compound ClC=1C=C(C(N)=CC=1S(=O)(=O)Cl)S(=O)(=O)Cl HMXFVSHKRGAWON-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- -1 aniline compound Chemical class 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F3/00—Biological treatment of water, waste water, or sewage
- C02F3/02—Aerobic processes
- C02F3/08—Aerobic processes using moving contact bodies
- C02F3/082—Rotating biological contactors
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W10/00—Technologies for wastewater treatment
- Y02W10/10—Biological treatment of water, waste water, or sewage
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biodiversity & Conservation Biology (AREA)
- Microbiology (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biological Treatment Of Waste Water (AREA)
Description
Fremgangsmåte til fremstilling av aminobenzen-disulfonylklorid-forbindelser. Process for the preparation of aminobenzene-disulfonyl chloride compounds.
Foreliggende oppfinnelse angår en The present invention relates to a
fremgangsmåte til fremstilling av aminobenzen-disulfonylklorid-forbindelser med process for the preparation of aminobenzene-disulfonyl chloride compounds with
den generelle formel: the general formula:
(i hvilken R betegner hydrogen, halogen, (in which R denotes hydrogen, halogen,
et lavere alkylradikal, • et lavere alkoxyra-dikail, enjnitro- eller en aminogruppe og R' a lower alkyl radical, • a lower alkoxyradical, enjnitro or an amino group and R'
betegner hydrogen eller et lavere alkylradikal), og det karakteristiske hovedtrekk denotes hydrogen or a lower alkyl radical), and the main characteristic feature
ved oppfinnelsen er at man omsetter en with the invention is that one converts one
forbindelse med den generelle formel connection with the general formula
i hvilken R og R' har den ovenfor angitte in which R and R' have the above indicated
betydning, og R" er hydrogen eller en sul-fonsyregruppe med klorsulfonsyre i nærvær av et alkålimetalll-halogenid. Ifølge en meaning, and R" is hydrogen or a sulfonic acid group with chlorosulfonic acid in the presence of an alkali metal halide. According to a
spesiell utførelsesform av oppfinnelsen particular embodiment of the invention
fremstilles 5-kloranilin-2,4-disulfonylkto-rid ved at man omsetter m-kloranilin med 5-chloroaniline-2,4-disulfonyl chloride is prepared by reacting m-chloroaniline with
klorsulfonsyre i nærvær av natriumklorid. chlorosulfonic acid in the presence of sodium chloride.
Fremgangsmåteproduktene ifølge oppfinnelsen kan fordelaktig anvendes som ut-gangsmaterialer ved fremstilling av kjemoterapeutiske midler, navnlig benzotia-diazin-l,l-dioxyd-forbindelser med diure-tiske og/eller natriuretiske egenskaper (pa-tent nr. 98 699). The process products according to the invention can advantageously be used as starting materials in the production of chemotherapeutic agents, in particular benzothia-diazine-1,1-dioxide compounds with diuretic and/or natriuretic properties (patent no. 98 699).
Klorsulfoneringen av anilinforbindel-sen utføres i nærvær av et alkalimetallha-logenid som f. eks. kloridet av natrium, ka-lium eller litium. For alle praktiske formål kan natriumklorid anvendes da det er lett tilgjengelig og billig, og reaksjonen går ganske glatt i nærvær av dette salt. Da reaksjonen mellom de nevnte bestanddeler ofte er ganske voldsom, foretrekkes det å' tilsette anilinderivatet til klorsulfonsyren dråpevis under omrøring og kjøling. Etter at alt anilinderivat er tilsatt, tilsetter man alkalimetallkloridet i små porsjoner så at utviklingen av hydrogenklorid kan foregå med moderat hastighet. Derpå oppvarmes blandingen til mellom omkring 100 og 200?^ f.. C, fortrinnsvis i et oljebad. , '<:; The chlorosulfonation of the aniline compound is carried out in the presence of an alkali metal halide such as, e.g. the chloride of sodium, potassium or lithium. For all practical purposes, sodium chloride can be used as it is readily available and cheap, and the reaction proceeds quite smoothly in the presence of this salt. As the reaction between the aforementioned components is often quite violent, it is preferred to add the aniline derivative to the chlorosulphonic acid dropwise while stirring and cooling. After all the aniline derivative has been added, the alkali metal chloride is added in small portions so that the evolution of hydrogen chloride can proceed at a moderate rate. The mixture is then heated to between about 100 and 200 °F, preferably in an oil bath. , '<:;
De følgende eksempler vil nærmere be-' lyse oppfinnelsen. -'i Eksempel 1: 64 g m-kloranilin (0,5 mol) ble dråpevis og under omrøring tilsatt til 375 ml klorsulfonsyre i en 3 liters trehalset: rund-kolbé, som ble avkjølet i isbad. Blandingen ble porsjonsvis og i et tidsrom på 1—2 timer tilsatt 350 g natriumklorid, hvorpå den ble oppvarmet gradvis til 150° C i et oljebad. Etter 3 timer ved 150—160° C ble kolben avkjølet grundig i et isbad og dens innhold behandlet med 1 liter koldt vann. Produktet ble ekstrahert med eter og ekstraktet vasket med-vann samt tørket over natrium-sulfat. -Etter fjernelse av eteren på dampbad ble residuet krystallisert fra en blan-ding av benzen og heksan, hvorved erholdtes 5-kloranilrn-2,4-disulfonylklorid med smeltepunkt 130—132° C. The following examples will explain the invention in more detail. -'i Example 1: 64 g of m-chloroaniline (0.5 mol) was added dropwise and with stirring to 375 ml of chlorosulfonic acid in a 3 liter three-necked: round flask, which was cooled in an ice bath. The mixture was added portionwise and over a period of 1-2 hours with 350 g of sodium chloride, after which it was heated gradually to 150° C. in an oil bath. After 3 hours at 150-160° C, the flask was thoroughly cooled in an ice bath and its contents treated with 1 liter of cold water. The product was extracted with ether and the extract washed with water and dried over sodium sulphate. -After removal of the ether on a steam bath, the residue was crystallized from a mixture of benzene and hexane, whereby 5-chloroanilrn-2,4-disulfonyl chloride with a melting point of 130-132° C was obtained.
Eksempel 2: 86 g m-bromanilin (0,5 mol) ble dra-pevis og i et tidsrom på 1 time tilsatt til i' 375 ml klorsulfonsyre som var kjølet i isbad. Blandingen ble tilsatt 350 g natriuim-klorfd i porsjoner i løpet av 2' timer, hvorpå den ble oppvarmet på oljebad til 150° C i 3 timer.. Etter grundig avkjøling i isbad ble reaksjonsblandingen behandlet med 1 liter isvann. Produktet ble tatt opp i eter, vasket med vann og tørket. Etter fjernelse av oppløsningsmidlet på dampbad erholdtes 5-bromanllin-2,4-disulfonylkloridet. Example 2: 86 g of m-bromoaniline (0.5 mol) was added dropwise over a period of 1 hour to 375 ml of chlorosulfonic acid which had been cooled in an ice bath. The mixture was added with 350 g of sodium chloride in portions over the course of 2 hours, after which it was heated in an oil bath to 150° C. for 3 hours. After thorough cooling in an ice bath, the reaction mixture was treated with 1 liter of ice water. The product was taken up in ether, washed with water and dried. After removing the solvent on a steam bath, the 5-bromannllin-2,4-disulfonyl chloride was obtained.
Eksempel 3: Ved i stedet for det i eksempel 2 an-vendte m-bromanilin å bruke en ekvimolar mengde m-toluidin (53,5 g) og gå frem i det vesentlige som beskrevet sammesteds, fikk man 5-metyIanilin-2,4-disulfonylklo-ridet. Example 3: By using an equimolar amount of m-toluidine (53.5 g) instead of the m-bromoaniline used in example 2 and proceeding essentially as described in the same place, 5-methylaniline-2,4 was obtained -disulfonyl chloride.
Eksempel 4: Ved i stedet for' det. i eksempel 2. an-vendte m-bromanilin å bruke en ekvimolar mengde 5-amino-2-klor-benzensulfon-syre og å gå frem i det vesentlige som beskrevet sammesteds, fikk man 4-kloranilin-2,5-disulfonylkloridet. Example 4: By instead of' that. in Example 2, using m-bromoaniline, using an equimolar amount of 5-amino-2-chloro-benzenesulfonic acid and proceeding essentially as described in the same place, the 4-chloroaniline-2,5-disulfonyl chloride was obtained.
Eksempel 5: 150 ml klorsulfonsyre ble tilsatt dråpevis under omrøring i løpet av 30 minut-ter til 24,6 g (0,2 mol) m-anisidin som var ; avkjølet i isbad. Etter at all klorsulfonsyre var tilsatt, ble 140 g natriumklorid tilsatt porsjonsvis i løpet av 1 time. Blandingen ble oppvarmet i 2 timer- på. dampbad og derpå 3 timer på oljebad til 150—160° C. Den ble så avkjølet, grundig i isbad og behandlet med 500 ml isvann. Produktet ble tatt opp i eter, vasket med vann og tør-ket, hvorpå oppløsningsmidlet ble avdam-pet på dampbad. Der erholdtes 5-metoxy-anilin-2,4-disulfonylklorid. Eksempel ff: Ved i stedet for det i eksempel 1 an-vendte m-kloranilin å bruke en ekvimolar mengde N-metyl-m-kloranilin og gå frem såledés som beskrevet i eksempel 1, fikk man N-metyl-5-kloranilin-2,4-disulfonyl-kloridet. Example 5: 150 ml of chlorosulfonic acid was added dropwise with stirring over the course of 30 minutes to 24.6 g (0.2 mol) of m-anisidine which was; cooled in an ice bath. After all the chlorosulfonic acid had been added, 140 g of sodium chloride was added portionwise over the course of 1 hour. The mixture was heated for 2 hours. steam bath and then 3 hours in an oil bath to 150-160° C. It was then cooled, thoroughly in an ice bath and treated with 500 ml of ice water. The product was taken up in ether, washed with water and dried, after which the solvent was evaporated on a steam bath. There was obtained 5-methoxy-aniline-2,4-disulfonyl chloride. Example ff: By instead of the m-chloroaniline used in example 1 using an equimolar amount of N-methyl-m-chloroaniline and proceeding as described in example 1, N-methyl-5-chloroaniline-2 was obtained ,4-disulfonyl chloride.
Eksempel 7: Ved i stedet for det i eksempel 1 an-vendte m-kloranilrh å bruke en ekvimolar mengde m-fluoraniiin. og. forøvrig gå frem hovedsakelig som i' eksempel 1, fikk man 5-fluoranilin-2,4-disulfonylkloEidet. Example 7: By instead of the m-chloroaniline used in example 1, an equimolar amount of m-fluoraniline is used. and. otherwise proceeding mainly as in example 1, 5-fluoroaniline-2,4-disulfonyl chloride was obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30658472A | 1972-11-15 | 1972-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO137591B true NO137591B (en) | 1977-12-12 |
| NO137591C NO137591C (en) | 1978-03-21 |
Family
ID=23185954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO438073A NO137591C (en) | 1972-11-15 | 1973-11-14 | APPLIANCE FOR BIOLOGICAL TREATMENT OF WASTEWATER |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5510317B2 (en) |
| CA (1) | CA1003583A (en) |
| CH (1) | CH593213A5 (en) |
| DE (1) | DE2357422C3 (en) |
| DK (1) | DK146362C (en) |
| FR (1) | FR2206282B1 (en) |
| GB (1) | GB1417920A (en) |
| NO (1) | NO137591C (en) |
| SE (1) | SE407679B (en) |
| ZA (1) | ZA738766B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107010798A (en) * | 2017-06-15 | 2017-08-04 | 盐城工学院 | A kind of waste water treatment reactor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1178601A (en) * | 1967-01-05 | 1970-01-21 | Nat Res Dev | Biological Treatment of Waste Water containing Organic Matter |
| US3575849A (en) * | 1968-12-05 | 1971-04-20 | Wilbur N Torpey | Biological treatment of wastewater |
-
1973
- 1973-11-09 CA CA185,546A patent/CA1003583A/en not_active Expired
- 1973-11-09 GB GB5216473A patent/GB1417920A/en not_active Expired
- 1973-11-13 SE SE7315377A patent/SE407679B/en unknown
- 1973-11-14 NO NO438073A patent/NO137591C/en unknown
- 1973-11-14 DE DE2357422A patent/DE2357422C3/en not_active Expired
- 1973-11-14 DK DK615073A patent/DK146362C/en not_active IP Right Cessation
- 1973-11-15 FR FR7340704A patent/FR2206282B1/fr not_active Expired
- 1973-11-15 CH CH1605973A patent/CH593213A5/xx not_active IP Right Cessation
- 1973-11-15 JP JP12867473A patent/JPS5510317B2/ja not_active Expired
- 1973-11-15 ZA ZA00738766A patent/ZA738766B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2206282A1 (en) | 1974-06-07 |
| FR2206282B1 (en) | 1980-07-04 |
| JPS5510317B2 (en) | 1980-03-14 |
| ZA738766B (en) | 1975-03-26 |
| CA1003583A (en) | 1977-01-11 |
| DK146362C (en) | 1984-02-27 |
| CH593213A5 (en) | 1977-11-30 |
| DK146362B (en) | 1983-09-19 |
| NO137591C (en) | 1978-03-21 |
| GB1417920A (en) | 1975-12-17 |
| DE2357422B2 (en) | 1978-02-16 |
| DE2357422A1 (en) | 1974-05-16 |
| JPS49124857A (en) | 1974-11-29 |
| SE407679B (en) | 1979-04-09 |
| DE2357422C3 (en) | 1978-10-12 |
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