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DE1158067B - Process for the production of organolithium compounds - Google Patents

Process for the production of organolithium compounds

Info

Publication number
DE1158067B
DE1158067B DEB61984A DEB0061984A DE1158067B DE 1158067 B DE1158067 B DE 1158067B DE B61984 A DEB61984 A DE B61984A DE B0061984 A DEB0061984 A DE B0061984A DE 1158067 B DE1158067 B DE 1158067B
Authority
DE
Germany
Prior art keywords
production
organolithium compounds
sodium
compounds
lithium
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
Application number
DEB61984A
Other languages
German (de)
Inventor
Phil Oliver Wallis Burke Ju Dr
Dr Oskar E H Klopfer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
OLIVER WALLIS BURKE JR
Original Assignee
OLIVER WALLIS BURKE JR
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US641047A external-priority patent/US3196116A/en
Application filed by OLIVER WALLIS BURKE JR filed Critical OLIVER WALLIS BURKE JR
Publication of DE1158067B publication Critical patent/DE1158067B/en
Pending legal-status Critical Current

Links

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
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/02—Lithium 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper 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
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C07F5/061—Aluminium compounds with C-aluminium linkage
    • C07F5/062—Al linked exclusively to C
    • 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
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F10/04—Monomers containing three or four carbon atoms
    • C08F10/06—Propene
    • 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
    • C08F114/00—Homopolymers 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 a halogen
    • C08F114/02—Monomers containing chlorine
    • C08F114/04—Monomers containing two carbon atoms
    • C08F114/06—Vinyl chloride
    • 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
    • C08F114/00—Homopolymers 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 a halogen
    • C08F114/18—Monomers containing fluorine
    • C08F114/26—Tetrafluoroethene
    • 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
    • C08F12/00—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 aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/06—Hydrocarbons
    • C08F12/08—Styrene
    • 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
    • C08F12/00—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 aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/16—Halogens
    • C08F12/18—Chlorine
    • 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
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
    • C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/42—Introducing metal atoms or metal-containing groups
    • 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
    • C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F110/02—Ethene
    • 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
    • C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F110/04—Monomers containing three or four carbon atoms
    • C08F110/06—Propene
    • 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
    • C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
    • C08F2410/04—Dual catalyst, i.e. use of two different catalysts, where none of the catalysts is a metallocene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Description

Es wurde gefunden, daß sich lithiumorganische Verbindungen in guter Ausbeute erhalten lassen, wenn man eine Mononatrium- oder Monokaliumkohlenwasserstoffverbindung mit wasserfreiem Lithiumchlorid umsetzt. Nach diesem Verfahren lassen sich aus polymeren oder nichtpolymeren Kohlenwasserstoffen mit einer oder mehreren einer Doppelbindung oder einem aromatischen Ring benachbarten Methylgruppe in glatter Reaktion lithiumorganische Verbindungen erhalten, indem man die Kohlenwasserstoffe zunächst mit einem Natriumoder Kaliumalkyl umsetzt und das hierbei gebildete Metallisierungsprodukt anschließend mit wasserfreiem Lithiumchlorid zur Reaktion bringt. Die erfindungsgemäße Metallisierungsreaktion wird dabei zweckmäßig unter Erwärmen und/oder Mahlen in der Kugelmühle ausgeführt, wobei man vorzugsweise in Gegenwart eines indifferenten Kohlenwasserstofflösungsmittels arbeitet.It has been found that organolithium compounds can be obtained in good yield, when using a monosodium or monopotassium hydrocarbon compound Reacts with anhydrous lithium chloride. Let after this procedure consist of polymeric or non-polymeric hydrocarbons with one or more one double bond or an aromatic ring adjacent methyl group in smooth reaction organolithium Compounds obtained by first treating the hydrocarbons with a sodium or Reacts potassium alkyl and the resulting metallization product then with anhydrous Brings lithium chloride to the reaction. The metallization reaction according to the invention is thereby expediently carried out with heating and / or grinding in the ball mill, preference being given to works in the presence of an inert hydrocarbon solvent.

Für die Polymerisation und Mischpolymerisation von Dienen, z. B. Isopren, geeignete Organolithiumverbindungen können durch direkte Einwirkung von Lithium auf einen halogenierten Kohlenwasserstoff oder auf ein solches Polymerisat hergestellt werden. Gemäß der Erfindung werden diese Verbindungen jedoch auf wirtschaftlichere Weise hergestellt, indem man auf einen mit Natrium oder Kalium metallierten Kohlenwasserstoff Lithiumchlorid einwirken läßt.For the polymerization and copolymerization of dienes, e.g. B. isoprene, suitable organolithium compounds can be caused by the direct action of lithium on a halogenated hydrocarbon or on such a polymer. According to the invention, these compounds however, made in a more economical way by metallizing on one with sodium or potassium Lets hydrocarbon lithium chloride act.

Bei der Herstellung der mit Lithium metallierten Verbindungen ist es wichtig, daß Feuchtigkeit, Luft und Kohlendioxyd während der Herstellung, Lagerung und Verwendung dieser Verbindungen ferngehalten werden.In the production of compounds metallized with lithium, it is important that moisture, air and carbon dioxide are kept away during the manufacture, storage and use of these compounds will.

Die mit Natrium metallierten Kohlenwasserstoffe können mit gleichen oder mit größeren oder geringeren als der stöchiometrischen Menge an wasserfreiem Lithiumchlorid umgesetzt werden.The hydrocarbons metallized with sodium can have the same or larger or smaller than the stoichiometric amount of anhydrous lithium chloride are implemented.

Das Verfahren gemäß der Erfindung wird zweckmäßigerweise in Gegenwart eines Kohlenwasserstoffes oder eines nicht reaktiven halogenierten Kohlenwasserstoffes als Verdünnungsmittel und vorzugsweise unter Verreiben oder Mahlen der Komponenten in der Kugelmühle in Abwesenheit von Luft, Feuchtigkeit und Kohlendioxyd ausgeführt.The process according to the invention is conveniently carried out in the presence of a hydrocarbon or a non-reactive halogenated hydrocarbon as a diluent and preferably with trituration or grinding of the components in the ball mill in the absence of air, Moisture and carbon dioxide running.

Geeignete Verdünnungsmittel für die Bildung der erfindungsgemäßen organometallischen Verbindungen sind Paraffine, Cycloparaffine, aromatische Kohlenwasserstoffe und halogenierte Paraffine, Cycloparaffine und aromatische Kohlenwasserstoffe (vorausgesetzt, daß diese hinreichend stabil sind, um die Metallisierungsreaktion nicht zu stören). Beispielsweise können Propan, Butan, Pentan, Hexan, Octan, Verfahren zur Herstellung
von lithiumorganischen VerbindungenSuitable diluents for the formation of the organometallic compounds according to the invention are paraffins, cycloparaffins, aromatic hydrocarbons and halogenated paraffins, cycloparaffins and aromatic hydrocarbons (provided that these are sufficiently stable so as not to interfere with the metallization reaction). For example, propane, butane, pentane, hexane, octane, methods of manufacture
of organolithium compounds

Anmelder:Applicant:

Dr. phil. Oliver Wallis Burke jun.,
ίο Pompano Beach, Fla. (V. St. A.)Dr. phil. Oliver Wallis Burke jun.,
ίο Pompano Beach, Fla. (V. St. A.)

Vertreter:Representative:

Dipl.-Chem. Dr. rer. nat. H. Kainer, Patentanwalt,
Heidelberg, Steubenstr. 22-24Dipl.-Chem. Dr. rer. nat. H. Kainer, patent attorney,
Heidelberg, Steubenstr. 22-24

Beanspruchte Priorität:Claimed priority:

V. St. v. Amerika vom 25. April 1956 und 19. Februar 1957
(Nr. 580 642 und Nr. 641047)V. St. v. America April 25, 1956 and February 19, 1957
(No. 580 642 and No. 641047)

Dr. phil. Oliver Wallis Burke jun.,Dr. phil. Oliver Wallis Burke jun.,

Pompano Beach, Fla.,Pompano Beach, Fla.,

und Dr. Oskar E. H. Klopfer,and Dr. Oskar E. H. Klopfer,

Clawson, Mich. (V. St. A.),Clawson, Me. (V. St. A.),

sind als Erfinder genannt wordenhave been named as inventors

Isooctan, Cyclohexan oder Methylcyclohexan verwendet werden.Isooctane, cyclohexane or methylcyclohexane can be used.

Die Erfindung wird an Hand des nachstehenden Beispiels erläutert:The invention is explained using the following example:

Beispielexample

Zur Herstellung von p-Xylyl-natrium wurden zu 5,3 g in einem Druckgefäß befindlichen p-Xylol (0,05MoI) 4,7 g m-Amyl-natrium (0,05MoI) in Form einer Suspension mit Natriumchlorid in 100 ml n-Pentan gegeben. Das im Druckgefäß befindliche Gemisch wird anschließend auf 65° C erhitzt und während 2 bis 3 Stunden unter Schütteln bei dieser Temperatur gehalten.For the production of p-xylyl sodium were to 5.3 g p-xylene (0.05 mol) in a pressure vessel 4.7 g m-amyl sodium (0.05 mol) in Given the form of a suspension with sodium chloride in 100 ml of n-pentane. The one in the pressure vessel The mixture is then heated to 65 ° C. and shaken for 2 to 3 hours held at this temperature.

6,7 g des so hergestellten p-Xylyl-natriums werden in eine Kugelmühle gegeben. Man fügt 2,1 g wasserfreies Lithiumchlorid (0,05 Mol) hinzu und beläßt über Nacht in der Kugelmühle, um den Metallaustausch zu vervollständigen. Nach Aufarbeitung erhält man p-Xylyl-lithium in nahezu theoretischer Ausbeute.6.7 g of the p-xylyl sodium thus produced will be placed in a ball mill. 2.1 g of anhydrous lithium chloride (0.05 mol) are added and left Ball mill overnight to complete metal exchange. After work-up p-xylyl-lithium is obtained in almost theoretical Yield.

309 750/410309 750/410

3 43 4

In gleicher Weise kann Lithiumamyl aus n-Amyl- daß man eine Mononatrium- oder Monokalium-In the same way, lithium amyl can be derived from n-amyl - that is, a monosodium or monopotassium

natrium und wasserfreiem LiDhiumchlorid hergestellt koUenwasserstoffverbindung mit wasserfreiem Li-sodium and anhydrous lithium chloride produced a hydrocarbon compound with anhydrous lithium

werden. thiumchlorid umsetzt.will. thium chloride converts.

Claims (1)

PATENTANSPRUCH: ,. ^ ^^ g&zogme PATENT CLAIM:,. ^^^ g &zogme Verfahren zur Herstellung von hthiumorgani- Deutsche Patentschrift Nr. 1 003 731;Process for the production of organophosphori- German Patent No. 1 003 731; sehen Verbindungen, dadurch gekennzeichnet, USA.-Patentschrift Nr. 1 938 180.see compounds characterized U.S. Patent No. 1,938,180. © 309 750/410 11.63© 309 750/410 11.63
DEB61984A 1956-04-25 1957-04-18 Process for the production of organolithium compounds Pending DE1158067B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58064256A 1956-04-25 1956-04-25
US641047A US3196116A (en) 1956-04-25 1957-02-19 Multiply metallated polymerization catalysts

Publications (1)

Publication Number Publication Date
DE1158067B true DE1158067B (en) 1963-11-28

Family

ID=27078095

Family Applications (3)

Application Number Title Priority Date Filing Date
DEB61982A Pending DE1168428B (en) 1956-04-25 1957-04-18 Process for the production of organometallic lithium compounds
DEB61984A Pending DE1158067B (en) 1956-04-25 1957-04-18 Process for the production of organolithium compounds
DEB44363A Pending DE1172429B (en) 1956-04-25 1957-04-18 Process for the polymerization of monomers having at least one polymerizable, olefinically unsaturated double bond or of mixtures of such monomers

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DEB61982A Pending DE1168428B (en) 1956-04-25 1957-04-18 Process for the production of organometallic lithium compounds

Family Applications After (1)

Application Number Title Priority Date Filing Date
DEB44363A Pending DE1172429B (en) 1956-04-25 1957-04-18 Process for the polymerization of monomers having at least one polymerizable, olefinically unsaturated double bond or of mixtures of such monomers

Country Status (5)

Country Link
BE (1) BE556975A (en)
DE (3) DE1168428B (en)
FR (1) FR1187677A (en)
GB (4) GB873657A (en)
NL (1) NL216658A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL265477A (en) * 1961-03-10
CN114656628B (en) * 2022-03-28 2023-11-17 浙江皇马科技股份有限公司 High molecular weight allyl alcohol polyoxyethylene polyoxypropylene ether and preparation method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1938180A (en) * 1931-06-23 1933-12-05 Shell Dev Process for the manufacture of organic metallo compounds
DE1003731B (en) 1955-02-25 1957-03-07 Basf Ag Process for the stabilization of organosodium compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE538782C (en) * 1931-11-16 Patra Patent Treuhand Electric arc lamp with a series resistor serving as a light body

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1938180A (en) * 1931-06-23 1933-12-05 Shell Dev Process for the manufacture of organic metallo compounds
DE1003731B (en) 1955-02-25 1957-03-07 Basf Ag Process for the stabilization of organosodium compounds

Also Published As

Publication number Publication date
GB873662A (en) 1961-07-26
BE556975A (en) 1957-10-25
GB873657A (en) 1961-07-26
FR1187677A (en) 1959-09-15
DE1172429B (en) 1964-06-18
GB873661A (en) 1961-07-26
DE1168428B (en) 1964-04-23
GB873660A (en) 1961-07-26
NL216658A (en) 1900-01-01

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