GB851651A - Polyphenyl ether compositions and their use as lubricants - Google Patents

Polyphenyl ether compositions and their use as lubricants

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Publication number
GB851651A
GB851651A GB39462/58A GB3946258A GB851651A GB 851651 A GB851651 A GB 851651A GB 39462/58 A GB39462/58 A GB 39462/58A GB 3946258 A GB3946258 A GB 3946258A GB 851651 A GB851651 A GB 851651A
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United Kingdom
Prior art keywords
meta
mixture
para
ethers
mixtures
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
Application number
GB39462/58A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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Filing date
Publication date
Application filed by Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB851651A publication Critical patent/GB851651A/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C391/00—Compounds containing selenium
    • C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings
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    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • G—PHYSICS
    • G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
    • G21C—NUCLEAR REACTORS
    • G21C5/00—Moderator or core structure; Selection of materials for use as moderator
    • G21C5/12—Moderator or core structure; Selection of materials for use as moderator characterised by composition, e.g. the moderator containing additional substances which ensure improved heat resistance of the moderator
    • G21C5/123—Moderators made of organic materials
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral salts thereof
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    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
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    • C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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    • C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/063—Ammonium or amine salts
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/32—Light or X-ray resistance
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • 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
    • 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
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E30/00—Energy generation of nuclear origin
    • Y02E30/30—Nuclear fission reactors

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Plasma & Fusion (AREA)
  • General Engineering & Computer Science (AREA)
  • High Energy & Nuclear Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises a mixture of two or more compounds of general formula: <FORM:0851651/IV(b)/1> where A is oxygen, sulphur, selenium or isopropylidene, at least 1/3 of the A's being oxygen atoms and not more than 1/3 being sulphur and/or selenium atoms, each n represents the number of substituent groups B attached to the phenyl radicals and may be O, B is tertiary butyl or alpha cumyl and at least 1/3 of the linkages A between the phenyl radicals, present in the whole mixture are in the meta position relative to another such linkage. Preferably the mixture of polyphenyl ethers has an average of 3-8 phenyl radicals per molecule, and preferably 40-100% of the linkages A are oxygen atoms and any remaining linkages A are isopropylidene radicals. It is also preferred that the mixture consists of at least 50% of components wherein all the A's are in meta positions relative to each other or consists of at least 60% of components wherein at least 2/3 of the A's are in meta positions relative to each other. Typical polyphenyl ethers which may be present in the mixtures are bis(meta, para, and ortho-phenoxyphenyl) ethers, meta and para-bis(meta and para-phenoxy-phenoxy)benzene, meta(meta-phenoxyphenoxy)(meta-tert.butylphenoxyphenoxy) benzene, and meta (metaalpha - cumylphenoxyphenoxy) (meta - phenoxy - phenoxy) benzene. A mixture of m-bis(m-phenoxyphenoxy)benzene with ortho and/or para isomers thereof may be used, the mol ratio of the meta ether to the other ethers being between 1:2 and 9:1. The mixtures may be obtained by simple mixing of the components but are conveniently obtained by reacting a mixture of alkali metal phenates with an appropriate monoor di-bromo-aryl compound, or by reacting a single alkali metal phenate with a mixture of mono- and/or dibromo aryl compounds. The reaction may be effected by heating the reactants for 0,5 to 10 hours at 150-300 DEG C. A copper catalyst may be present. Included in specified phenates are potassium meta-phenoxyphenate, potassium meta alpha-cumyl phenate, sodium meta-phenoxy (para-tert. butyl phenate), the sodium salt of p-hydroxy diphenyl thioether, and the potassium salt of m-hydroxy diphenyl selenide. Included in specified bromo aryl compounds are 1-alpha cumyl-3-bromobenzene, dimethyl (m-tert.-butylphenyl)(m-bromophenyl) methane, phenyl (m-bromophenyl)ether, o, m, and p-dibromobenzenes, 1-tert. butyl-3,5-dibromobenzene, and 1-alpha cumyl-3,4 or 2,5, or 3,6, or 4,6, or 3,5-dibromobenzene. The mixtures may be used as lubricants, heat exchange fluids, or hydraulic fluids.ALSO:A mixture of two or more polyphenyl ethers having the formula: <FORM:0851651/III/1> (wherein the A's stand for oxygen, sulphur, or selenium, or for isopropylidene, at least 1/3 of the A's being oxygen atoms and not more than 1/3 being sulphur and/or selenium atoms, each n being the number of substituent groups attached to the phenyl radicals and being zero or a whole number, the B's representing tertiary butyl or alpha-cumyl groups, and at least 1/3 of the linkages A in the whole mixture being in meta position relative to another such linkage) are used as lubricants in engines operating at high temperatures such as aircraft and gas turbine engines, and also as lubricants, heat exchanger fluids or hydraulic fluids in radiation-emitting apparatus. Polyphenyl ether mixtures having an average of 3-8 phenyl radicals per molecule are preferred. Specified polyphenyl ethers which may be present in the mixtures are bis(meta, para, and ortho-phenoxyphenyl) ethers, meta and para-bis(meta and para-phenoxyphenoxy) benzenes, and m(m-alpha-cumylphenoxyphenoxy) (m-phenoxyphenoxy) benzene. A mixture of m-bis(m-phenoxyphenoxy) benzene with o- and/or p-isomers thereof may be used, the mol ratio of the meta ether to the other ethers being between 1:2 and 9:1. The mixtures may be obtained by simple mixture of the components or by reacting suitable alkali meta-phenates with a mixture of mono- and/or dibromo aryl compounds. The polyphenyl ether mixtures may be used alone or with additives such as pour-point depressants, anti-oxidants, anti-corrosive agents, viscosity index improvers, anti-lacquering agents, and extreme-pressure additives. Specified additives include polymers of esters of acrylic, methacrylic, and other 2-alkyl acrylic acids; salts of aromatic carboxylic acids (e.g. alkyl salicylic acids) or of phenols (including alkylamino and other substituted phenols) with Group II metals; trialkyl, triaryl, and trialkaryl phosphates, and halo-alkylphosphonates such as monobutyl hydrogen trichloromethyl-phosphonate and its amine salts e.g. its salt with di(2-ethylhexyl) amine.
GB39462/58A 1957-12-09 1958-12-08 Polyphenyl ether compositions and their use as lubricants Expired GB851651A (en)

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US70129657A 1957-12-09 1957-12-09

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BE (1) BE573694A (en)
CH (1) CH412162A (en)
DE (1) DE1128068B (en)
FR (1) FR1215972A (en)
GB (1) GB851651A (en)
NL (2) NL233984A (en)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3169925A (en) * 1961-06-26 1965-02-16 Shell Oil Co High temperature lubricants and phosphorus containing polymers
US3173873A (en) * 1962-01-23 1965-03-16 Monsanto Res Corp Functional fluid compositions
US3226325A (en) * 1963-04-30 1965-12-28 Monsanto Res Corp Lubricant composition containing a halophenol
US3226323A (en) * 1963-04-30 1965-12-28 Monsanto Res Corp Lubricant composition containing a haloalkanoic compound
US3236773A (en) * 1963-05-08 1966-02-22 Monsanto Res Corp Lubricant composition containing a metal compound
US3244627A (en) * 1962-01-23 1966-04-05 Monsanto Res Corp Functional fluid compositions
US3244629A (en) * 1962-02-13 1966-04-05 Monsanto Res Corp Polyphenyl ether compositions containing an organotin thiocyanate
US3267032A (en) * 1963-06-27 1966-08-16 Ravner Harold Metal antioxidants for fluid bis (phenoxyphenoxy) benzene
US3314887A (en) * 1964-01-02 1967-04-18 Monsanto Co Functional fluid compositions
US3360467A (en) * 1965-03-29 1967-12-26 Monsanto Res Corp Functional fluid
US3383314A (en) * 1964-01-02 1968-05-14 Monsanto Co Aryl ferrocene antioxidants in polyphenyl oxa and thia ether functional fluids
US3409552A (en) * 1964-04-01 1968-11-05 Chevron Res Alkyl aryl ether polymers in lubricants
US3490737A (en) * 1966-08-26 1970-01-20 Monsanto Co Functional fluid compositions
US3492229A (en) * 1966-08-26 1970-01-27 Monsanto Co Functional fluid compositions
US3718590A (en) * 1970-09-25 1973-02-27 Monsanto Co Polyphenyl thioether lubricating compositions
US3844962A (en) * 1970-12-30 1974-10-29 Monsanto Co Polyphenyl trioether lubricating compositions

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3451061A (en) * 1958-10-13 1969-06-17 Monsanto Co Functional fluid compositions
DE1202284B (en) * 1959-10-05 1965-10-07 Dow Chemical Co Process for isomerizing halogenated diphenyloxides
DE1191828B (en) * 1960-02-05 1965-04-29 Shell Int Research Process for the production of polyphenyl ethers
DE1192214B (en) * 1960-04-22 1965-05-06 Shell Int Research Process for the production of almost chlorine- or bromine-free mixtures of aromatic polyethers
NL264937A (en) * 1960-05-20
NL292095A (en) * 1962-04-30
DE1247325B (en) * 1963-03-11 1967-08-17 Monsanto Co Process for color improvement and for stabilizing polyphenyl ethers against oxidation and corrosion
GB1047306A (en) * 1963-08-07
US4976882A (en) * 1987-10-08 1990-12-11 Exxon Chemical Patents, Inc. Alkyl phenol-sulfur condensates as fuel and lubricating oil additives

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3169925A (en) * 1961-06-26 1965-02-16 Shell Oil Co High temperature lubricants and phosphorus containing polymers
US3173873A (en) * 1962-01-23 1965-03-16 Monsanto Res Corp Functional fluid compositions
US3244627A (en) * 1962-01-23 1966-04-05 Monsanto Res Corp Functional fluid compositions
US3244629A (en) * 1962-02-13 1966-04-05 Monsanto Res Corp Polyphenyl ether compositions containing an organotin thiocyanate
US3226325A (en) * 1963-04-30 1965-12-28 Monsanto Res Corp Lubricant composition containing a halophenol
US3226323A (en) * 1963-04-30 1965-12-28 Monsanto Res Corp Lubricant composition containing a haloalkanoic compound
US3236773A (en) * 1963-05-08 1966-02-22 Monsanto Res Corp Lubricant composition containing a metal compound
US3267032A (en) * 1963-06-27 1966-08-16 Ravner Harold Metal antioxidants for fluid bis (phenoxyphenoxy) benzene
US3314887A (en) * 1964-01-02 1967-04-18 Monsanto Co Functional fluid compositions
US3383314A (en) * 1964-01-02 1968-05-14 Monsanto Co Aryl ferrocene antioxidants in polyphenyl oxa and thia ether functional fluids
US3409552A (en) * 1964-04-01 1968-11-05 Chevron Res Alkyl aryl ether polymers in lubricants
US3360467A (en) * 1965-03-29 1967-12-26 Monsanto Res Corp Functional fluid
US3490737A (en) * 1966-08-26 1970-01-20 Monsanto Co Functional fluid compositions
US3492229A (en) * 1966-08-26 1970-01-27 Monsanto Co Functional fluid compositions
US3718590A (en) * 1970-09-25 1973-02-27 Monsanto Co Polyphenyl thioether lubricating compositions
US3720614A (en) * 1970-09-25 1973-03-13 Monsanto Co Polyphenyl thioether lubricating compositions
US3844962A (en) * 1970-12-30 1974-10-29 Monsanto Co Polyphenyl trioether lubricating compositions
US3844961A (en) * 1970-12-30 1974-10-29 Monsanto Co Polyphenyl thioether lubricating compositions

Also Published As

Publication number Publication date
FR1215972A (en) 1960-04-21
BE573694A (en)
NL233984A (en)
DE1128068B (en) 1962-04-19
NL107472C (en)
CH412162A (en) 1966-04-30

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