Classifications

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  • 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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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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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
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/283—Esters of polyhydroxy compounds
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/287—Partial esters
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/287—Partial esters
  • C10M2207/289—Partial esters containing free hydroxy groups
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  • 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
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  • 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
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  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/06—Perfluorinated compounds
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  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/08—Halogenated waxes
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/064—Di- and triaryl amines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/064—Di- and triaryl amines
  • C10M2215/065—Phenyl-Naphthyl amines
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
  • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
  • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
  • C10M2219/064—Thiourea type compounds
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
  • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
  • C10M2219/066—Thiocarbamic type compounds
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
  • C10M2219/106—Thiadiazoles
• • C—CHEMISTRY; METALLURGY
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/135—Steam engines or turbines

Definitions

• This invention is for improvements in or relating to lubricants which are to be used under conditions which tend to disrupt the lubricant film, which disruption more particularly takes place when the pressure between the bearing surfaces is very great.
• the film rupture strength becomes more important than the coeflicient of friction. For example, under the extreme pressures obtaining in hypoid gears, if the oil film is ruptured, the metal surfaces will contact one with the other, thereby leading to loss of eificiency, excessive wear and ultimately to failure of the mechanism.
• lubricants which have a high film-rupture strength. Such lubricants are generally known in the trade as extremepressure lubricants.
• extreme-pressure lubricants originally consisted of lubricating oil which contained sulphur, either in the form of flowers of sulphur or as a colloidal dispersion.
• the sulphur was liable to precipitation and it was later proposed to prepare these extreme-pressure lubricants by treating a fatty oil, for example, an animal oil, with thionyl-chloride or with similar reagents, such as sulphur monochloride, sulphur dichloride, etc, and then to add the product of this reaction to a mineral oil.
• a large number of organic compounds have been proposed for use as extreme pressure agents, including various types of organic di and polysulphides, and the corresponding derivatives of selenium and tellurium. While the higher polysulphides are very effective in increasing the film rupture strength of the oil in which they are dissolved, they tend to be inherently unstable, corrosive, especially to copper and cuprous materials, and to exert a pro-oxidant effect upon the oil.
• the disulphides usually possess rather poor extreme pressure properties, insufficient to warrant their use except in conjunction with other extreme pressure additives such as organic halogen compounds.
• oils used for turbine lubrication consist of specially selected mineral oil blends stabilised against oxidation by the incorporation of antioxidant additives and containing also additives designed to protect fer rous metal parts against rusting or corrosion by, e. g., sea water. It is of course important that additional additives, incorporated in such oils for the purpose of enhancing their extreme pressure properties, should not interfere in any way with the normal functions of the two foregoing classes of additive.
• Many turbine oils, especially marine turbine oils used by the Admiralty are controlled as regards oxidation stability, salt water corrosion of ferrous metals, demulsification value and corrosive action on cuprous metals, by a very rigid specification. It is necessary, therefore, that extreme pressure additives incorporated therein should not adversely affect compliance with its clauses.
• chlorine compounds generally tend to promote oxidation and are also prone to hydrolysis with the subsequent libersubstituted in the alpha position by dior polysulphide groups, and the corresponding derivatives of selenium or tellurium and may be represented by the general formula:
• radical R is an alkyl, aryl or cycloalkyl 3 radical
• X is sulphur, selenium or tellurium and n is 2, 3 or 4.
• the radicals R may contain halogen substituents, although as already indicated the presence of halogen is to be avoided if the compounds are to be used in certain applications, particularly in the turbine oils.
• ester groups situated in the alpha position to the dior polysulphide groups exerts an activating influence with the consequent production of extreme pressure properties substantially in excess of those obtainable by the use of the simple aliphatic, aromatic or aryl substituted aliphatic dior polysulphides.
• a lubricating composition comprises a mineral lubricating oil base and a minor proportion, sufficient substantially to increase the load-carrying capacity of the oil, of an ester of acetic acid substituted in the alpha position by sulphur, selenium or tellurium said ester having the general formula where R, is an alkyl, aryl or cycloalkyl radical which may contain halogen substituents, X is sulphur, selenium or tellurium and n is 2, 3 or 4.
• the invention includes a turbine oil comprising a mineral lubricating oil base containing agents controlling oxidation stability and corrosion of ferrous metals and including also a minor proportion, sufiicient substantially to increase the load-carrying capacity of the oil, of an ester of acetic acid substituted in the alpha position by sulphur, selenium or tellurium said ester having the general formula where R is an alkyl, aryl or cycloalkyl radical, X is sulphur, selenium or tellurium and n is 2, 3 or 4.
• the additive compounds referred to above are new and have not been prepared heretofore, they may be prepared by methods known to the art. Thus, they may be prepared by the reaction of the corresponding oc-ChlOlO or abromo esters with sodium dior poly-sulphides in alcoholic solution, or by oxidation or the a-mercapto esters to give the corresponding disulphides, or by reaction of the amercapto esters with sulphur dichloride or sulphur mono-chloride in a non-ionising solvent to give the triand tetra-sulphides respectively.
• the deep red solution so obtained was cooled to about 30 C. and 28 grams (0.1 mol.) of n-butyl monochloracetate was added dropwise with continuous stirring and cooling maintaining the temperature below about 60 C.
• the mixture was diluted with water to about 500 ccs. total volume and the reaction product extracted with petroleum ether.
• the product was a pale yellow liquid with a characteristic odour.
• the product resembled the disulphide in appearance.
• the product was a yellow liquid.
• Di tB-chloroethyl) dithiodiacetate prepared similarly from pl-chloroethyl chloracetate, which was prepared by reacting chloracetyl chloride with ethylene chlorhydrin.
• Aryl esters such as diphenyl dithiodiacetate cannot readily be prepared by the foregoing methods as hydrolysis of the esters appears to take place. They may, however, be prepared via the Bunte salts by a. method similar to that described by Stoner and Dougherty in the Journal of the American Chemical Society, vol. 63, p. 987 (1941). Thus, for example, phenyl monochloracetate may be reacted in boiling 50 aqueous alcohol with sodium thiosulphate, and the product converted tov the disulphide by the addition of iodine.
• Yields are usually rather poor and it is therefore generally preferred to employ the alkyl or cycloalkyl esters.
• Selenium compounds such as di(nbuty1) diseleno-diacetate may be prepared by reacting the a-halo ester e. g. n-butyl, monochloracetate with sodium or potassium selenosulphate in aqueous alcoholic solution by the method employed by Stoner and Williams in the Journal of the American Chemical Society, vol. 70, page 1113 (1948).
• a-halo ester e. g. n-butyl, monochloracetate
• sodium or potassium selenosulphate sodium or potassium selenosulphate
• the additives used will of necessity be soluble in the mineral oil base in the proportions in which they are to be employed.
• the preferred compounds are those which are miscible with oil in all proportions, although others of lower solubility may be satisfactorily used.
• the oil solubility will necessarily depend upon the nature of the groups R but in general complete miscibility with. oil. may be achieved by employing as radical R an aliphatic or cycloaliphatic radical having not less than four carbon atoms.
• The. amounts of the additives employed. will depend upon the purpose for which the oil is to be. used. Any quantity from the minimum suflicient to impart a substantial increase in film rupture strength up to about per cent may be employed, but in general from about 0.5. per cent. to about 2.0 per cent is contemplated, especially for use in turbine oils.
• antioxidant additives which may be of. the alkylated phenol type, e. g,.,, tertiary butyl cresol, 2.14 dimethyl-B-tertiary butyl phenol, 2:6 di-tertiary butyl-p-cresol, or sec.- ondary aromatic amines, e. g., diphenylamine,
• phenyl a naphthylamine phenyl-s-naphthylamine, and also anti-rusting additives which may be of various types, one preferred class of additives being the acid esters of the long-chain mono esters. of polyhydric alcohols described in patent application No. 191,166.
• a copper stain inhibitor of the type disclosed in Patent No. 2,414,257 e. g., mercaptobenzothiazole, benzothiazoledisulphide, benzothiazole hydroxymethyl sulphide, or tetramethyl or tetraethyl thiuram disulphide.
• the additives of the present invention may, if desired, be employed in conjunction with organic halogenated compounds in mineral lubricating oils to provide, for example, extreme pressure lubricants for hypoid gears. Oils containing such combinations of additives are capable of withstanding higher loads than oils which contain only the sulphur compound. As already stated, however, the presence of halogen compounds in turbine oils is undesirable.
• the additives were dissolved in a mineral oil blend (oil A) consisting of 70%. of a mineral .oil having a viscosity of about 170 seconds Redwood at 140 F. and 30% of a solvent refined mineral oil having a viscosity of about 65 seconds Redwood at 140 F.
• oil A consisting of 70%. of a mineral .oil having a viscosity of about 170 seconds Redwood at 140 F. and 30% of a solvent refined mineral oil having a viscosity of about 65 seconds Redwood at 140 F.
• the radicals R shall consist of alkyl ute, respectively, the sliding velocity being 3775 radicals having not more than six carbon atoms. feet per minute.
• the discs were immersed in To illustrate the effectiveness of the comthe oil under test, which was maintained at pounds of the present invention when employed 155-165 F., and the load on the discs was gradfor the purpose of imparting extreme pressure ually increased until scuffing took place.
• Oil C was a typical turbine oil of additives of the present invention on the propsimilar viscosity to oil B and containing antierties of oil B: oxidant and rust inhibitors.
• Salt water corrosion test I. P. 125/51 (1951 edition, page 390) (modified in respect of salt water composition and duration, to comply with the requirements of British Admiralty Specification OM88).
• the additives of the present invention not only greatly enhanced the load-carrying capacity of the turbine oil in which they were dissolved, but also left unaffected the essential properties of the oil, i. e., low acidity, low demulsification value, high resistance to oxidation and ability to inhibit corrosion of ferrous metals by salt water.
• oils D a relatively viscous mineral oil blend
• oil D which consisted of 27 parts by weight of a conventionally refined Pennsylvanian bright stock of viscosity 600 seconds Redwood at F., 34 parts of a conventionally refined Mid-Continent Failure Oil
• Di(n-butyl) dithiodiacetate 0.2% Mercaptobenzothlazol 91.9% Oil D B Hexachlorethaue 89.8% our) 3% DMZ-ethyl hexyl) trlthiodiacetatei: 0.1% Tetraethyl thiuram disulphide
• a lubricating composition comprising a mineral oil containing a small amount sufficient to increase the load-carrying capacity of the oil of an ester of acetic acid substituted in the alpha position by an element selected from the group consisting of sulphur and selenium, said ester having the general formula in which R is a radical selected from the group consisting of alkyl, aryl and cycloalkyl radicals, X is an element selected from the group consisting of sulphur and selenium and n is an integer from 2 to 4 inclusive.
• a lubricating composition comprising a mineral oil containing a small amount suflicient to increase the load-carrying capacity of the oil of an ester of acetic acid substituted in the alpha position by an element selected from the group consisting of sulphur and selenium, said ester having the general formula ROOC.CH2 (X) n-CH2-COOR in which R is a chlorine containing radical selected from the group consisting of alkyl, aryl and cycloalkyl radicals, X is an element selected from the group consisting of sulphur and selenium and n is an integer from 2' to 4 inclusive.
• a lubricating composition comprising a mineral oil containing about 0.5% to about by weight of an ester of acetic acid substituted in the alpha position by an element selected from the group consisting of sulphur and selenium, said ester having the general formula in which R is a radical selected from the group consisting of alkyl, aryl and cycloalkyl radicals, X is an element selected from the group consisting of sulphur and selenium and n is an integer from 2 to 4 inclusive.
• a lubricating composition comprising a mineral oil containing from 0.5% to 2.0% by weight of an ester of acetic acid substituted in the alpha position by an element selected from the group consisting of sulphur and selenium, said ester having the general formula ROOC.CH2 (X) n-CH2COOR ll) in which R is a radical selected from the group consisting of alkyl, aryl and cycloalkyl radicals, X is an element selected from the group consisting of sulphur and selenium and n is an integer from 2 to 4 inclusive.
• a lubricating composition comprising a mineral oil containing a small amount suflicient to increase the load-carrying capacity of the oil of an ester of acetic acid substituted in the alpha position by an element selected from the group consisting of sulphur and selenium, said ester having the general formula in which R is an alkyl radical containing not more than six carbon atoms X is an element selected from the group consisting of sulphur and selenium and n is an integer from 2 to 4 inclusive.
• a lubricating composition comprising a mineral oil containing from 0.5% to 2.0% by weight of an ester of acetic acid substituted in the alpha position by an element selected from the group consisting of sulphur and selenium, said ester having the general formula ROOC.CH2- (X) n--CH2.COOR
• R is an alkyl radical containing not more than six carbon atoms
• X is an element selected from the group consists of sulphur and selenium and n is an integer from 2 to 4 inclusive.
• a lubricating composition as claimed in claim 1 in which there is also incorporated a small amount of a compound selected from the group consisting of mercapto-arylene-thiazoles and derivatives of mercapto-arylene-thiazoles.
• a lubricating composition as claimed in claim 1 in which there is also incorporated a small amount of an alkyl thiuram disulphide.
• a lubricating composition as claimed in claim 1 in which there is also incorporated a small amount of berizothiazole disulphide.
• a lubricating composition comprising a mineral oil containing as an additive from 0.5% to 2.0% by weight of di(n-butyl) dithiodiacetate.
• a lubricating composition comprising a mineral oil containing as an additive from 0.5% to 2.0% by weight of di(n-butyl) trithiodiacetate.
• a turbine oil comprising a mineral oil containing agents controlling oxidation stability and corrosion of ferrous metals and including also a small amount suificient to increase the load-carrying capacity of the oil of an ester of acetic acid substituted in the alpha position by an element selected from the group consisting of sulphur and selenium, said ester having the general formula ROOC.CH2 (X) n-CHaCOOR in which R is a radical selected from the group consisting of alkyl, aryl and cycloalkyl radicals, X is an element selected from the group consisting of sulphur and selenium and n is an integer from 2 to 4 inclusive.
• An extreme pressure lubricant comprising a lubricating oil composition as claimed in claim 1 and including in addition to the ester of acetic acid an organic halogenated compound.

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

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Citations (5)

• 0
  • BE BE510842D patent/BE510842A/xx unknown
  • NL NL75960D patent/NL75960C/xx active
• 1951
  • 1951-04-23 GB GB9430/51A patent/GB714497A/en not_active Expired
• 1952
  • 1952-04-15 US US282472A patent/US2691000A/en not_active Expired - Lifetime
  • 1952-04-21 FR FR1058007D patent/FR1058007A/fr not_active Expired
  • 1952-04-22 DE DEW8403A patent/DE942586C/de not_active Expired

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