CH615411A5 - - Google Patents
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- Publication number
- CH615411A5 CH615411A5 CH1510374A CH1510374A CH615411A5 CH 615411 A5 CH615411 A5 CH 615411A5 CH 1510374 A CH1510374 A CH 1510374A CH 1510374 A CH1510374 A CH 1510374A CH 615411 A5 CH615411 A5 CH 615411A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- chloride
- trans
- racemization
- cis
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 27
- 230000006340 racemization Effects 0.000 claims description 23
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 7
- -1 cyclopropane-l-carboxylic acid halides Chemical class 0.000 claims description 7
- 150000007517 lewis acids Chemical class 0.000 claims description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- VNTCVNLNEOVBEE-JGVFFNPUSA-N (1s,3s)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carbonyl chloride Chemical compound CC(C)=C[C@H]1[C@H](C(Cl)=O)C1(C)C VNTCVNLNEOVBEE-JGVFFNPUSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 3
- 238000006345 epimerization reaction Methods 0.000 description 3
- XLOPRKKSAJMMEW-JGVFFNPUSA-N (-)-trans-chrysanthemic acid Chemical compound CC(C)=C[C@H]1[C@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-JGVFFNPUSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical group OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 2
- XLOPRKKSAJMMEW-YUMQZZPRSA-N (+)-cis-chrysanthemic acid Chemical compound CC(C)=C[C@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-YUMQZZPRSA-N 0.000 description 1
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- IVGYSSJKFLEVIX-UHFFFAOYSA-N (-(E)-Pyrethrolone Natural products CC1=C(CC=CC=C)C(=O)CC1O IVGYSSJKFLEVIX-UHFFFAOYSA-N 0.000 description 1
- XLOPRKKSAJMMEW-HTQZYQBOSA-N (-)-cis-chrysanthemic acid Chemical compound CC(C)=C[C@@H]1[C@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-HTQZYQBOSA-N 0.000 description 1
- IVGYSSJKFLEVIX-SNAWJCMRSA-N (E)-pyrethrolone Chemical compound CC1=C(C\C=C\C=C)C(=O)CC1O IVGYSSJKFLEVIX-SNAWJCMRSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- VNTCVNLNEOVBEE-UHFFFAOYSA-N 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carbonyl chloride Chemical compound CC(C)=CC1C(C(Cl)=O)C1(C)C VNTCVNLNEOVBEE-UHFFFAOYSA-N 0.000 description 1
- FVWYNQLWRKLYJF-UHFFFAOYSA-N 3-(cyclohexylidenemethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C1CCCCC1 FVWYNQLWRKLYJF-UHFFFAOYSA-N 0.000 description 1
- VBNQMVZJHJDIKD-UHFFFAOYSA-N 3-(cyclopentylidenemethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C1CCCC1 VBNQMVZJHJDIKD-UHFFFAOYSA-N 0.000 description 1
- CAOJXVMGSRHFGB-UHFFFAOYSA-N 3-ethenyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C)C1C(O)=O CAOJXVMGSRHFGB-UHFFFAOYSA-N 0.000 description 1
- KZYVOZABVXLALY-UHFFFAOYSA-N 4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)CC1O KZYVOZABVXLALY-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- CXBMCYHAMVGWJQ-UHFFFAOYSA-N tetramethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (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 |
|---|---|---|---|
| JP12750273A JPS5337858B2 (US06397114-20020528-M00001.png) | 1973-11-12 | 1973-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615411A5 true CH615411A5 (US06397114-20020528-M00001.png) | 1980-01-31 |
Family
ID=14961548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1510374A CH615411A5 (US06397114-20020528-M00001.png) | 1973-11-12 | 1974-11-12 |
Country Status (11)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206140A (en) * | 1966-08-26 | 1980-06-03 | Roussel Uclaf | Novel cyclopropanecarboxylic acids and esters |
| JPS52144651A (en) * | 1976-05-24 | 1977-12-02 | Sumitomo Chem Co Ltd | Racemization of optical active 2,2-dimethyl-3-(1-alkenyl)-cyclopropane-1-carboxylic acid |
| JPS57163341A (en) * | 1981-03-30 | 1982-10-07 | Sumitomo Chem Co Ltd | Preparation of racemized cyclopropanecarboxylic acid derivative |
| US4473703A (en) * | 1981-03-30 | 1984-09-25 | Sumitomo Chemical Company, Limited | Method of epimerization of alkyl chrysanthemate |
| JPS5869831A (ja) * | 1981-10-22 | 1983-04-26 | Sumitomo Chem Co Ltd | （＋）−トランス第一菊酸の製造法 |
| EP0155765B1 (en) * | 1984-02-22 | 1988-10-05 | Sumitomo Chemical Company, Limited | Method for racemization of chrysanthemic acid or its ester |
| HU200310B (en) * | 1984-06-15 | 1990-05-28 | Sumitomo Chemical Co | Process for racemizing chrisanthemic acid and esters and for transforming raceme cys isomeres into raceme trans isomeres |
| JPS62198643A (ja) * | 1986-02-27 | 1987-09-02 | Sumitomo Chem Co Ltd | ラセミ第一菊酸類の製造法 |
| HU202171B (en) * | 1986-09-04 | 1991-02-28 | Sumitomo Chemical Co | Process for racemization of chrysanthemic acid and its esters, as well as for conversion of the racemic mixture |
| EP0282221B1 (en) * | 1987-03-09 | 1992-01-15 | Sumitomo Chemical Company, Limited | Method for racemization of optically active chrysanthemic acid or its ester |
| HU203513B (en) * | 1987-04-28 | 1991-08-28 | Sumitomo Chemical Co | Process for racemizing and trans-isomerizing optically active chrisanthemic acid derivatives |
| JPH0688933B2 (ja) * | 1987-07-17 | 1994-11-09 | 住友化学工業株式会社 | 光学活性第一菊酸類のラセミ化法 |
| EP0342843B1 (en) * | 1988-05-19 | 1993-03-03 | Sumitomo Chemical Company, Limited | Process for preparing racemic dihalovinylcyclopropane carboxylic acid halides |
| US5840958A (en) * | 1996-10-17 | 1998-11-24 | Fmc Corporation | 1S to 1R Epimerizations of pyrethroid intermediates |
| CN114539045B (zh) * | 2020-11-18 | 2023-07-21 | 中国科学院大连化学物理研究所 | 一种反式左旋菊酸的消旋化方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2038019A5 (US06397114-20020528-M00001.png) * | 1969-03-22 | 1970-12-31 | Sumitomo Chemical Co |
-
1973
- 1973-11-12 JP JP12750273A patent/JPS5337858B2/ja not_active Expired
-
1974
- 1974-11-08 CA CA213,346A patent/CA1025475A/en not_active Expired
- 1974-11-08 FR FR7437188A patent/FR2250728B1/fr not_active Expired
- 1974-11-08 US US05/522,130 patent/US3989750A/en not_active Expired - Lifetime
- 1974-11-11 GB GB4864374A patent/GB1448316A/en not_active Expired
- 1974-11-11 SU SU742078312A patent/SU722479A3/ru active
- 1974-11-11 DK DK586374A patent/DK586374A/da not_active Application Discontinuation
- 1974-11-11 IT IT70311/74A patent/IT1024802B/it active
- 1974-11-12 CH CH1510374A patent/CH615411A5/de not_active IP Right Cessation
- 1974-11-12 BE BE150378A patent/BE822046A/xx not_active IP Right Cessation
- 1974-11-12 NL NL7414766A patent/NL7414766A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2250728B1 (US06397114-20020528-M00001.png) | 1976-12-31 |
| DE2453639A1 (de) | 1975-05-15 |
| FR2250728A1 (US06397114-20020528-M00001.png) | 1975-06-06 |
| CA1025475A (en) | 1978-01-31 |
| JPS5077346A (US06397114-20020528-M00001.png) | 1975-06-24 |
| JPS5337858B2 (US06397114-20020528-M00001.png) | 1978-10-12 |
| US3989750A (en) | 1976-11-02 |
| DK586374A (US06397114-20020528-M00001.png) | 1975-07-14 |
| DE2453639B2 (de) | 1977-06-23 |
| IT1024802B (it) | 1978-07-20 |
| GB1448316A (en) | 1976-09-02 |
| SU722479A3 (ru) | 1980-03-15 |
| BE822046A (fr) | 1975-05-12 |
| NL7414766A (nl) | 1975-05-14 |
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