GB1114782A - Production of fluoroethylene derivatives - Google Patents
Production of fluoroethylene derivativesInfo
- Publication number
- GB1114782A GB1114782A GB19268/65A GB1926865A GB1114782A GB 1114782 A GB1114782 A GB 1114782A GB 19268/65 A GB19268/65 A GB 19268/65A GB 1926865 A GB1926865 A GB 1926865A GB 1114782 A GB1114782 A GB 1114782A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- reaction
- c8f17i
- iodo
- c10f21i
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/22—Tin compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/304—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/015—Dispersions of solid lubricants
- C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Abstract
1:1 Adducts (with respect to the ethylenic or acetylenic bond) are obtained by reacting an ethylenically or acetylenically unsaturated organic silicon compound containing at least one hydrogen atom, with an iodofluoroalkane having at least one -CF2CF2- group which is an a -iodoperfluoroalkane, a -iodoperfluorochloroalkane, a - iodo - o - hydroperfluoroalkane, a - diodo - o - hydroperfluorochloroalkane, a - iodo - o - haloperfluoroalkane (the halogen being Cl, Br or I) or an a -iodo-o -haloperfluorochloroalkane (the halogen being Br or I), at a temperature above 170 DEG C., a pressure below 5 atmospheres and residence time below 2 hours. In examples: (7) C10F21I is reacted with CH2 = CHSiCl3. The product is dissolved in methanol or ethylene glycol and the solution is hydrogenated or treated with NaHSO3 to give C10F21CH2CH2Si(OR)3, where R is CH3 or HOCH2CH2. R may also be derived from triethyleneglycol. (14) C10F21I is reacted with CH2 = CHSiCl2.CH3, the product dissolved in tetrahydrofuran and treated successively with concentrated aqueous ammonia and zinc turnings to obtain a fluoroalkylsilazane. An iodine-free product is obtained by extracting the silazane with CHCl:CCl2, adding ammonia and expelling the CHCl:CCl2 while hot by ammonia steam. (15) C10F21I is reacted with CH2 = CHCH2SiCl3 and the product treated as in (14). (16) C10F21I is reacted with CH2=CHSiCl (CH3)2 and the product dissolved in tetrahydrofuran and treated successively with ammonia solution, zinc turnings and HCl gas to give C10F21CH2CH2SiCl(CH3)2, which can be hydrogenated with LiAlH4 to give the corresponding hydrogen silane, which can itself be added to unsaturated organic compounds, e.g. with methyl acrylate to give C10F21CH2CH2Si(CH3)2 C2H4COOCH3. Other unsaturated silicon compounds for reaction with the iodofluoroalkanes are listed. Trichlorosilane, methyldichlorosilane and methyl hydrogen polysiloxane can add to the double bond of perfluorooctyl cyclohex-1-ene.ALSO:The compounds C7F15CH2CH2I, PhC2H4C8F17 and <FORM:1114782/C4-C5/1> are of use as lubricants.ALSO:Perfluorocaprylic acid C7F15COOH is obtained by electro-fluorination of C3H7CF2CH2CH2COOH.ALSO:1:1-Adducts (with respect to the ethylenic or acetylenic bond) are obtained by reacting an ethylenically or acetylenically unsaturated organic compound containing at least one hydrogen atom, with an iodofluoroalkane having at least one -CF2CF2- group which is an a -iodoperfluoroalkane, a -iodoperfluorochloroalkane, a -iodo-o -hydroperfluoroalkane, a iodo - o -hydroperfluorochloroalkane, a - iodo - o -haloperfluoroalkane (the halogen being Cl, Br or I) or an a - iodo - o -haloperfluorochloroalkane (the halogen being Br or I), at a temperature above 170 DEG C., a pressure below 5 atmospheres and residence time below 2 hours. Secondary reactions may involve loss of iodine or hydrogen iodide, and may be completed after the reaction by catalytic hydrogenation or treatment with a base. In examples, ethylene is reacted with C4F9I, C6F13I, C7F15I, C8F17I and C10F21 to give RfCH2Ch2I; and with I(CF2)6I to give ICH2CH2(CF2)6CH2CH2I and some I(CF2)6CH2CH2I; acetylene and H(CF2)8I give ICH: CH(CF2)8H; CH2: CCl2 and Cl(CF2)6I give Cl(CF2)6CH2CCl2I, which can be saponified to Cl(CF2)6CH2COOH; 1-octene and C8F17I after reaction and treatment with Zn and HCl give C8H17 C8F17; as in the previous example, cyclohexene and C8F17I give perfluorooctylcyclohexane or the initial product treated with NaOH gives perfluorooctylcyclohex-1-ene, which can add Br2; butadiene and C8F17I give C8F17CH2CH: CHCH2I, which with Na acetate, Na malonic ester or Na acetylacetone gives the expected product with elimination of NaI; allyl chloride and C8F17I after reaction and treatment with NaOH give C8F17CH: CHCH2Cl, in which by reaction with NaBr or NaI the Cl can be replaced by Br or I, or which by hydrolysis gives the alcohol; styrene and C8F17I after reaction and treatment with Na/Hg give PhCH2CH2C8F17, which can be sulphonated or sulphochlorinated; and allylbenzene and C8F17I after reaction and treatment with Na/Hg give PhC3H6C8F17, which can be sulphonated. Other reactants are specified, including organo-tin compounds. In addition, propene and ICF2-CF2I after reaction and hydrogenation gives ICF2CF2CH2CH2CH3, which on reaction with acrylonitrile and hydrogenation gives C3H7CF2CF2CH2CH2CN, which can be saponified to the free acid.ALSO:The 1:1 adducts of perfluroalkyl iodides with unsaturated compounds or their further reaction products (see Divisions C2 and C3) are used for impregnating textiles and other materials for dirt -, oil - and water-repellency. Thus (1) C10F21CH2CH2SiCl3 can be used for textiles and paper, and a solution in CCl4 can be used for impregnating a textile fabric by dipping or spraying; textiles, leather, paper and cellulose regenerates can be impregnated by treatment with a solution of C10F21CH2CH2Si (OR)3, where ROH is methanol, ethylene glycol or triethylene glycol, in CHCl : CCl2; (2) the adduct from C10F21I and CH2 = CHSiCl2-CH3, dissolved in tetrahydrofuran and treated successively with concentrated aqueous ammonia and zinc turnings, gives an aqueous solution suitable for impregnating textiles; or the fluoroalkylsilazane can be extracted with CHCl:CCl2 and this solution washed with concentrated aqueous ammonia and then diluted and used for impregnating textiles; or an iodine-free product is obtained by expelling the CHCl : CCl2 from the hot suspension with the NH4OH by ammonia steam, and the resulting aqueous solution can be used for impregnating textiles, paper and leather (e.g. cotton); (3) the adduct from C10F21I and CH2 = CHCH2 SiCl3 can be treated as in (2) and the products similarly used. It is also stated that a spray which is a solution, in Freons (Trade Mark) or chlorinated hydrocarbons, of a wax or oil containing such adducts may be used for impregnation of textiles.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB0076756 | 1964-05-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1114782A true GB1114782A (en) | 1968-05-22 |
Family
ID=6979205
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB19268/65A Expired GB1114782A (en) | 1964-05-14 | 1965-05-07 | Production of fluoroethylene derivatives |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS5127646B1 (en) |
AT (1) | AT269089B (en) |
BE (1) | BE663752A (en) |
CH (1) | CH459161A (en) |
DE (1) | DE1443519A1 (en) |
GB (1) | GB1114782A (en) |
NL (1) | NL143546B (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5453528A (en) * | 1994-06-01 | 1995-09-26 | Dow Corning Corporation | Optimized process for inert fluorinated silanes |
WO2008019111A2 (en) * | 2006-08-03 | 2008-02-14 | Great Lakes Chemical Corporation | Telomer compositions and production processes |
EP2058430A1 (en) * | 2007-11-08 | 2009-05-13 | Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO | Hydrophobic surface finish and method of application |
US7985286B2 (en) | 2008-11-24 | 2011-07-26 | Xerox Corporation | Solid inks with lower coefficient of friction |
US8956456B2 (en) | 2009-07-30 | 2015-02-17 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Apparatus and method for atomic layer deposition |
US9297077B2 (en) | 2010-02-11 | 2016-03-29 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Method and apparatus for depositing atomic layers on a substrate |
US9416449B2 (en) | 2010-02-18 | 2016-08-16 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Continuous patterned layer deposition |
US9761458B2 (en) | 2010-02-26 | 2017-09-12 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Apparatus and method for reactive ion etching |
CN115770594A (en) * | 2021-09-06 | 2023-03-10 | 浙江省化工研究院有限公司 | Preparation method and application of hydrophobic catalyst |
-
1964
- 1964-05-14 DE DE19641443519 patent/DE1443519A1/en active Granted
-
1965
- 1965-05-07 GB GB19268/65A patent/GB1114782A/en not_active Expired
- 1965-05-11 BE BE663752A patent/BE663752A/xx unknown
- 1965-05-11 CH CH656965A patent/CH459161A/en unknown
- 1965-05-12 NL NL656506069A patent/NL143546B/en unknown
- 1965-05-13 AT AT433765A patent/AT269089B/en active
- 1965-05-14 JP JP40028017A patent/JPS5127646B1/ja active Pending
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5453528A (en) * | 1994-06-01 | 1995-09-26 | Dow Corning Corporation | Optimized process for inert fluorinated silanes |
WO2008019111A2 (en) * | 2006-08-03 | 2008-02-14 | Great Lakes Chemical Corporation | Telomer compositions and production processes |
WO2008019111A3 (en) * | 2006-08-03 | 2008-06-05 | Great Lakes Chemical Corp | Telomer compositions and production processes |
AU2008325361B2 (en) * | 2007-11-08 | 2013-02-07 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Hydrophobic surface finish and method of application |
WO2009061199A1 (en) * | 2007-11-08 | 2009-05-14 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Hydrophobic surface finish and method of application |
EP2058430A1 (en) * | 2007-11-08 | 2009-05-13 | Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO | Hydrophobic surface finish and method of application |
US9017760B2 (en) | 2007-11-08 | 2015-04-28 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Hydrophobic surface finish and method of application |
US7985286B2 (en) | 2008-11-24 | 2011-07-26 | Xerox Corporation | Solid inks with lower coefficient of friction |
US8956456B2 (en) | 2009-07-30 | 2015-02-17 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Apparatus and method for atomic layer deposition |
US9297077B2 (en) | 2010-02-11 | 2016-03-29 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Method and apparatus for depositing atomic layers on a substrate |
US9803280B2 (en) | 2010-02-11 | 2017-10-31 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Method and apparatus for depositing atomic layers on a substrate |
US10676822B2 (en) | 2010-02-11 | 2020-06-09 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Method and apparatus for depositing atomic layers on a substrate |
US9416449B2 (en) | 2010-02-18 | 2016-08-16 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Continuous patterned layer deposition |
US9761458B2 (en) | 2010-02-26 | 2017-09-12 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Apparatus and method for reactive ion etching |
CN115770594A (en) * | 2021-09-06 | 2023-03-10 | 浙江省化工研究院有限公司 | Preparation method and application of hydrophobic catalyst |
Also Published As
Publication number | Publication date |
---|---|
DE1443519A1 (en) | 1968-11-07 |
AT269089B (en) | 1969-03-10 |
NL6506069A (en) | 1965-11-15 |
CH459161A (en) | 1968-07-15 |
JPS5127646B1 (en) | 1976-08-13 |
BE663752A (en) | 1965-09-01 |
NL143546B (en) | 1974-10-15 |
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