DE1298514B - Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern - Google Patents
Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethernInfo
- Publication number
- DE1298514B DE1298514B DEF47817A DEF0047817A DE1298514B DE 1298514 B DE1298514 B DE 1298514B DE F47817 A DEF47817 A DE F47817A DE F0047817 A DEF0047817 A DE F0047817A DE 1298514 B DE1298514 B DE 1298514B
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- radical
- mol
- preparation
- carbon atoms
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 22
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 12
- 239000011698 potassium fluoride Substances 0.000 claims description 12
- 235000003270 potassium fluoride Nutrition 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- -1 perfluorinated aliphatic ethers Chemical class 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- YZIQRUBSHCOAJB-UHFFFAOYSA-N 1,1,1,2-tetrafluoro-3-[3,4,4,4-tetrafluoro-3-(trifluoromethyl)butan-2-yl]oxy-2-(trifluoromethyl)butane Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(C)OC(C)C(F)(C(F)(F)F)C(F)(F)F YZIQRUBSHCOAJB-UHFFFAOYSA-N 0.000 description 1
- CRJVPUWOURIOCW-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,2-pentafluoroethane Chemical compound CCOC(F)(F)C(F)(F)F CRJVPUWOURIOCW-UHFFFAOYSA-N 0.000 description 1
- DCEPGADSNJKOJK-UHFFFAOYSA-N 2,2,2-trifluoroacetyl fluoride Chemical compound FC(=O)C(F)(F)F DCEPGADSNJKOJK-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- RJFWXWNWUNDRLN-UHFFFAOYSA-N 2-(1,1,1,2,3,3,3-heptafluoropropan-2-yloxymethyl)oxirane Chemical compound FC(F)(F)C(F)(C(F)(F)F)OCC1CO1 RJFWXWNWUNDRLN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OIEGKKVOQKREAU-UHFFFAOYSA-N FC(C(COCC(C(C(F)(F)F)(C(F)(F)F)F)Cl)Cl)(C(F)(F)F)C(F)(F)F Chemical compound FC(C(COCC(C(C(F)(F)F)(C(F)(F)F)F)Cl)Cl)(C(F)(F)F)C(F)(F)F OIEGKKVOQKREAU-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 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
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- RUFILLDBEINNQV-UHFFFAOYSA-N dodecyl methanesulfonate Chemical compound CCCCCCCCCCCCOS(C)(=O)=O RUFILLDBEINNQV-UHFFFAOYSA-N 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003983 inhalation anesthetic agent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F16/14—Monomers containing only one unsaturated aliphatic radical
- C08F16/24—Monomers containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/28—Preparation of ethers by reactions not forming ether-oxygen bonds from acetals, e.g. by dealcoholysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF47817A DE1298514B (de) | 1965-12-02 | 1965-12-02 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF49222A DE1294949B (de) | 1965-12-02 | 1966-05-17 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF50760A DE1302054B (de) | 1965-12-02 | 1966-11-25 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF50759A DE1301807B (de) | 1965-12-02 | 1966-11-25 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| ES0333931A ES333931A1 (es) | 1965-12-02 | 1966-11-29 | Procedimiento para la obtencion de perfluoalquil-alquil-eteres. |
| CH1711366A CH479514A (de) | 1965-12-02 | 1966-11-30 | Verfahren zur Herstellung einseitig perfluorierter aliphatischer Äther |
| NL6616938A NL6616938A (enrdf_load_html_response) | 1965-12-02 | 1966-12-01 | |
| FR85937A FR1506638A (fr) | 1965-12-02 | 1966-12-02 | éthers perfluoralkyl-alkyliques et leur préparation |
| BE690605D BE690605A (enrdf_load_html_response) | 1965-12-02 | 1966-12-02 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF47817A DE1298514B (de) | 1965-12-02 | 1965-12-02 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF49222A DE1294949B (de) | 1965-12-02 | 1966-05-17 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF50760A DE1302054B (de) | 1965-12-02 | 1966-11-25 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF50759A DE1301807B (de) | 1965-12-02 | 1966-11-25 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1298514B true DE1298514B (de) | 1969-07-03 |
Family
ID=27436944
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF47817A Pending DE1298514B (de) | 1965-12-02 | 1965-12-02 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF49222A Pending DE1294949B (de) | 1965-12-02 | 1966-05-17 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF50760A Pending DE1302054B (de) | 1965-12-02 | 1966-11-25 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF50759A Pending DE1301807B (de) | 1965-12-02 | 1966-11-25 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF49222A Pending DE1294949B (de) | 1965-12-02 | 1966-05-17 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF50760A Pending DE1302054B (de) | 1965-12-02 | 1966-11-25 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| DEF50759A Pending DE1301807B (de) | 1965-12-02 | 1966-11-25 | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE690605A (enrdf_load_html_response) |
| CH (1) | CH479514A (enrdf_load_html_response) |
| DE (4) | DE1298514B (enrdf_load_html_response) |
| FR (1) | FR1506638A (enrdf_load_html_response) |
| NL (1) | NL6616938A (enrdf_load_html_response) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846502A (en) * | 1971-08-02 | 1974-11-05 | Airco Inc | 2-methoxy-3-h-perfluorobutane |
| US4522995A (en) * | 1983-05-02 | 1985-06-11 | E. I. Du Pont De Nemours And Company | Fluorinated alkyl ether-containing ethylenes, precursors thereto, and copolymers thereof with tetrafluoroethylene |
| BE1001430A6 (fr) * | 1988-02-05 | 1989-10-31 | Charlier Andre | Hache-betteraves. |
| US5925611A (en) * | 1995-01-20 | 1999-07-20 | Minnesota Mining And Manufacturing Company | Cleaning process and composition |
| US6506459B2 (en) | 1995-01-20 | 2003-01-14 | 3M Innovative Properties Company | Coating compositions containing alkoxy substituted perfluoro compounds |
| US6548471B2 (en) | 1995-01-20 | 2003-04-15 | 3M Innovative Properties Company | Alkoxy-substituted perfluorocompounds |
| US5718293A (en) * | 1995-01-20 | 1998-02-17 | Minnesota Mining And Manufacturing Company | Fire extinguishing process and composition |
| WO1996036688A1 (en) | 1995-05-16 | 1996-11-21 | Minnesota Mining And Manufacturing Company | Azeotrope-like compositions and their use |
| US6008179A (en) | 1995-05-16 | 1999-12-28 | 3M Innovative Properties Company | Azeotrope-like compositions and their use |
| CN1192088C (zh) * | 1995-05-16 | 2005-03-09 | 美国3M公司 | 共沸物状组合物及其应用 |
| KR100474764B1 (ko) | 1995-12-15 | 2005-08-05 | 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 | 세정방법및세정조성물 |
| US5827446A (en) * | 1996-01-31 | 1998-10-27 | E. I. Du Pont De Nemours And Company | Nonafluoromethoxybutane compositions |
| US5750797A (en) * | 1996-04-15 | 1998-05-12 | Minnesota Mining And Manufacturing Company | Process for the production of hydrofluoroethers |
| US6030934A (en) * | 1997-02-19 | 2000-02-29 | 3M Innovative Properties Company | Azeotropic compositions of methoxy-perfluoropropane and their use |
| US6552090B1 (en) | 1997-09-15 | 2003-04-22 | 3M Innovative Properties Company | Perfluoroalkyl haloalkyl ethers and compositions and applications thereof |
| US6462228B1 (en) | 1997-12-22 | 2002-10-08 | 3M Innovative Properties Company | Process for preparation of fluorinated sulfinates |
| US6022842A (en) * | 1998-02-11 | 2000-02-08 | 3M Innovative Properties Company | Azeotrope-like compositions including perfluorobutyl methyl ether, 1- bromopropane and alcohol |
| US6046368A (en) * | 1998-03-17 | 2000-04-04 | 3M Innovative Properties Company | Catalytic process for making hydrofluoroethers |
| CA2255413A1 (en) | 1998-12-11 | 2000-06-11 | Fracmaster Ltd. | Foamed nitrogen in liquid co2 for fracturing |
| US6127430A (en) * | 1998-12-16 | 2000-10-03 | 3M Innovative Properties Company | Microemulsions containing water and hydrofluroethers |
| US6159917A (en) * | 1998-12-16 | 2000-12-12 | 3M Innovative Properties Company | Dry cleaning compositions containing hydrofluoroether |
| US6148634A (en) | 1999-04-26 | 2000-11-21 | 3M Innovative Properties Company | Multistage rapid product refrigeration apparatus and method |
| US6297308B1 (en) | 1999-10-07 | 2001-10-02 | 3M Innovative Properties Company | Chemical compositions |
| US6310018B1 (en) | 2000-03-31 | 2001-10-30 | 3M Innovative Properties Company | Fluorinated solvent compositions containing hydrogen fluoride |
| US6372700B1 (en) | 2000-03-31 | 2002-04-16 | 3M Innovative Properties Company | Fluorinated solvent compositions containing ozone |
| US7385089B2 (en) | 2005-12-23 | 2008-06-10 | 3M Innovative Properties Company | Fluorochemical ketone compounds and processes for their use |
| US8791254B2 (en) | 2006-05-19 | 2014-07-29 | 3M Innovative Properties Company | Cyclic hydrofluoroether compounds and processes for their preparation and use |
| US7824755B2 (en) | 2006-06-29 | 2010-11-02 | 3M Innovative Properties Company | Fluorinated leveling agents |
| US8193397B2 (en) | 2006-12-06 | 2012-06-05 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
-
1965
- 1965-12-02 DE DEF47817A patent/DE1298514B/de active Pending
-
1966
- 1966-05-17 DE DEF49222A patent/DE1294949B/de active Pending
- 1966-11-25 DE DEF50760A patent/DE1302054B/de active Pending
- 1966-11-25 DE DEF50759A patent/DE1301807B/de active Pending
- 1966-11-30 CH CH1711366A patent/CH479514A/de not_active IP Right Cessation
- 1966-12-01 NL NL6616938A patent/NL6616938A/xx unknown
- 1966-12-02 FR FR85937A patent/FR1506638A/fr not_active Expired
- 1966-12-02 BE BE690605D patent/BE690605A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1301807B (de) | 1969-08-28 |
| CH479514A (de) | 1969-10-15 |
| DE1294949B (de) | 1969-05-14 |
| NL6616938A (enrdf_load_html_response) | 1967-06-05 |
| BE690605A (enrdf_load_html_response) | 1967-06-02 |
| DE1302054B (de) | 1970-02-05 |
| FR1506638A (fr) | 1967-12-22 |
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