GB662650A - Synthetic lubricants - Google Patents

Synthetic lubricants

Info

Publication number
GB662650A
GB662650A GB31034/48A GB3103448A GB662650A GB 662650 A GB662650 A GB 662650A GB 31034/48 A GB31034/48 A GB 31034/48A GB 3103448 A GB3103448 A GB 3103448A GB 662650 A GB662650 A GB 662650A
Authority
GB
United Kingdom
Prior art keywords
atoms
ether
aliphatic hydrocarbon
oxygen
thio
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
GB31034/48A
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.)
Standard Oil Development Co
Original Assignee
Standard Oil Development Co
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 to US52428A priority Critical patent/US2575195A/en
Application filed by Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to GB31034/48A priority patent/GB662650A/en
Priority to FR990983D priority patent/FR990983A/en
Publication of GB662650A publication Critical patent/GB662650A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; 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
    • 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
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Abstract

A complex ester is prepared by esterifying an aliphatic dicarboxylic acid with an equimolar proportion of a glycol until half the theoretical water of esterification has been evolved, and then esterifying the unreacted carboxyl and hydroxyl groups of the half ester with a monohydric aliphatic alcohol and a monocarboxylic aliphatic acid respectively. Esters may have the formul R11OOC-R-COO-R1-OOC-R111 or R11OOC-COO-R1-OOC-R111, where R may be a series of saturated C2 or higher aliphatic hydrocarbon radicals linked by one or more ether-oxygen and/or thio-ester sulphur atoms, the total number of C, O, and S atoms being 3-80, and the number of S atoms not more than 2; R1 may be a series of saturated C2 or higher aliphatic hydrocarbon radicals linked by one or more ether-oxygen and/or thio-ether sulphur atoms, the total number of C, O, and S atoms being 5-80, and the number of S atoms not more than 2; R11 may be a series of saturated C2 or higher aliphatic hydrocarbon radicals linked by 1-5 ether-oxygen and/or thio-ether sulphur atoms, the total number of C, O and S atoms being 4-20, and the number of S atoms no more than 2; and R111 may be a series of C2 or higher aliphatic hydrocarbon radicals linked by 1-5 ether-oxygen atoms, there being at least one carbon atom between the carboxyl group and the nearest ether-oxygen atom, and the total number of C and O atoms is 3-22. The molecular weight should be at least 300. Preferred dicarboxylic acids are straight-chain acids of the paraffinic group having 6-10 carbon atoms. Preferred monohydric alcohols are aliphatic primary alcohols of 6-10 carbon atoms, and preferred monocarboxylic acids are C2-C10 fatty acids. The glycols include polyethylene or propylene glycols, and glycols containing thio or ether linkages. Monohydric alcohols include ether alcohols and "oxo" alcohols.ALSO:A complex ester is prepared by esterifying an aliphatic dicarboxylic acid with an equimolar proportion of a glycol until half the theoretical water of esterification has been evolved, and then esterifying the unreacted carboxyl and hydroxyl groups of the half ester with a monohydric aliphatic alcohol and a monocarboxylic aliphatic acid respectively. Esters for use as lubricants may have the formul R11OOC-R-COO-R1-OOCR111 or R11OOC-COO-R1-OOCR111, where R is an aliphatic hydrocarbon radical of 1-26 carbon atoms or a series of saturated C2 or higher aliphatic hydrocarbon radicals linked by one or more ether-oxygen and/or thio-ether sulphur atoms, the total number of C, O and S atoms being 3-80, and the number of S atoms not more than 2; R1 is a saturated C2 to C18 aliphatic hydrocarbon radical or a series of saturated C2 or higher aliphatic hydrocarbon radicals linked by one or more ether-oxygen and/or thio-ether sulphur atoms, the total number of C, O and S atoms being 5-80, and the number of S atoms not more than 2; R11 is a C1 to C20 aliphatic hydrocarbon radical or a series of saturated C2 or higher aliphatic hydrocarbon radicals linked by 1-5 ether-oxygen and/or thio-ether sulphur atoms, the total number of C, O and S atoms being 4-20, and the number of S atoms not more than 2; and R111 is a C1 to C22 aliphatic hydrocarbon radical or a series of C2 or higher aliphatic hydrocarbon radicals linked by 1-5 ether-oxygen atoms, there being at least one carbon atom between the carboxyl group and the nearest ether-oxygen atom, and the total number of C and O atoms is 3-22 or R111 is two aliphatic hydrocarbon groups linked by one thio-ether sulphur atom separated from the carboxyl group by at least one carbon atom, and the total number of carbon atoms is 2-21. The molecular weight should be at least 300. Preferred dicarboxylic acids are straight chain acids of the paraffinic group having 6-10 carbon atoms. Preferred monohydric alcohols are aliphatic primary alcohols of 6-10 carbon atoms, and preferred monocarboxylic acids are C2-C10 fatty acids. The glycols include ethylene glycol and its homologues containing up to 18 carbon atoms, polyethylene or propylene glycols, and glycols containing thio or ether linkages, e.g. thiodiglycol, 1,2-bis-(2-hydroxyethylmercapto) - ethane, and bis-[2-(2-hydroxyethoxy)-ethyl]-sulphide. Monohydric alcohols include ether alcohols and " oxo " alcohols. Esterification may be effected in toluene with p-toluene sulphonic acid monohydrate as catalyst. Properties are given of esters prepared from adipic, sebacic, C14-C18 or C10 to C12 alkenylsuccinic acids; thiodiglycol, tri-, tetra- or higher poly-ethylene glycol, tri- or penta-methylene glycol; n-caproic, n-caprylic, n-butyric or 2-ethylcaproic acid; and 2-ethylhexanol, C10 or C15-C19 " oxo " alcohol or methyl alcohol.ALSO:A complex ester is prepared by esterifying an aliphatic dicarboxylic acid with an equimolar proportion of a glycol until half the theoretical water of esterification has been evolved, and then esterifying the unreacted carboxyl and hydroxyl groups of the half ester with a monohydric aliphatic alcohol and a monocarboxylic aliphatic acid respectively. Esters for use as lubricants which may be blended with mineral lubricating oils, antioxidants, viscosity index improvers, thickeners, pour depressants, dyes, &c. may have the formul R"OOC-R-COO-R\sv-OOC R"\sv or R"OOC-COO-R\sv-OOC R"\sv, where R is an aliphatic hydrocarbon radical of 1-26 carbon atoms or a series of saturated C2 or higher aliphatic hydrocarbon radicals linked by one or more ether-oxygen and/or thio-ether sulphur atoms, the total number of C, O, and S atoms being 3-80, and the number of S atoms not more than 2; R\sv is a saturated C2 to C18 aliphatic hydrocarbon radical or a series of saturated C2 or higher aliphatic hydrocarbon radicals linked by one or more ether-oxygen and/or thio-ether sulphur atoms, the total number of C, O, and S atoms being 5-80, and the number of S atoms not more than 2; R" is a C1 to C20 aliphatic hydrocarbon radical or a series of saturated C2 or higher aliphatic hydrocarbon radicals linked with 1-5 ether-oxygen and/or thio-ether sulphur atoms, the total number of C, O, and S atoms being 4-20, and the number of S atoms no more than 2; and R"\sv is a C1 to C22 aliphatic hydrocarbon radical or a series of C2 or higher aliphatic hydrocarbon radicals linked by 1-5 ether-oxygen atoms, there being at least one carbon atom between the carboxyl group and the nearest ether-oxygen atom, and the total number of C and O atoms is 3-22 or R"\sv is two aliphatic hydrocarbon groups linked by one thio-ether sulphur atom separated from the carboxyl group by at least one carbon atom, and the total number of carbon atoms is 2-21. The molecular weight should be at least 300. Preferred dicarboxylic acids are straight chain acids of the paraffinic group having 6-10 carbon atoms. Preferred monohydric alcohols are aliphatic primary alcohols of 6-10 carbon atoms, and prefered monocarboxylic acids are C2-C10 fatty acids. The glycols include ethylene glycol and its homologues containing up to 18 carbon atoms, polyethylene or propylene glycols, and glycols containing thio or ether linkages, e.g., thiodiglycol, 1, 2-bis-(2-hydroxyethylmercapto)ethane, and bis - [2 - (2-hydroxyethoxy)ethyl] sulphide. Monohydric alcohols include ether alcohols and "oxo" alcohols. Properties are given of esters prepared from adipic, sebacic, C14-C18 or C10 to C12 alkenylsuccinic acids; thiodiglycol, tri-, tetra- or higher poly-ethylene glycol, tri- or penta-methylene glycol; n-caproic, n-caprylic, n-butyric or 2-ethyl-caproic acid; and 2-ethylhexanol, C10 or C15-C19 "oxo" alcohol or methyl alcohol.
GB31034/48A 1948-10-01 1948-11-30 Synthetic lubricants Expired GB662650A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US52428A US2575195A (en) 1948-10-01 1948-10-01 Dibasic acid esters and method for producing them
GB31034/48A GB662650A (en) 1948-11-30 1948-11-30 Synthetic lubricants
FR990983D FR990983A (en) 1948-11-30 1949-07-21 Synthetic lubricants

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB31034/48A GB662650A (en) 1948-11-30 1948-11-30 Synthetic lubricants

Publications (1)

Publication Number Publication Date
GB662650A true GB662650A (en) 1951-12-12

Family

ID=10316935

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31034/48A Expired GB662650A (en) 1948-10-01 1948-11-30 Synthetic lubricants

Country Status (3)

Country Link
US (1) US2575195A (en)
FR (1) FR990983A (en)
GB (1) GB662650A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1011109B (en) * 1955-12-19 1957-06-27 Geigy Co Ltd lubricant
DE1135445B (en) * 1953-07-02 1962-08-30 Exxon Research Engineering Co Process for the preparation of complex esters which can be used as lubricating oils or lubricating oil components
US3547693A (en) * 1968-01-12 1970-12-15 Eastman Kodak Co Magnetic tape
US5820777A (en) 1993-03-10 1998-10-13 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5851968A (en) 1994-05-23 1998-12-22 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants
US5906769A (en) 1992-06-03 1999-05-25 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5976399A (en) 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US6221272B1 (en) 1992-06-03 2001-04-24 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors

Families Citing this family (24)

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Publication number Priority date Publication date Assignee Title
US2782166A (en) * 1949-05-07 1957-02-19 Exxon Research Engineering Co Ester base lubricating greases
US2705724A (en) * 1951-05-24 1955-04-05 Exxon Research Engineering Co Reduction of acidity in synthetic ester lubes with olefin oxides
NL173612B (en) * 1951-12-28 Iten K Ag SCREEN PRINT TEMPLATE WITH PERIODIC HOLE PATTERN.
US2723957A (en) * 1952-02-27 1955-11-15 Exxon Research Engineering Co Synthetic lubricating oils containing paraffinic resins
US2751351A (en) * 1952-07-05 1956-06-19 Exxon Research Engineering Co Complex ester base lubricating grease compositions
US2712527A (en) * 1952-08-26 1955-07-05 Exxon Research Engineering Co Improved lubricating greases containing dihydroxy stearic acid soap
US2768139A (en) * 1952-10-20 1956-10-23 Exxon Research Engineering Co Lubricating greases from oxo glycols
US2926139A (en) * 1952-11-08 1960-02-23 Bayer Ag Lubricants for refrigerating systems
GB757241A (en) * 1953-09-17 1956-09-19 Wakefield & Co Ltd C C Improvements in or relating to lubricating compositions
US2820815A (en) * 1954-04-08 1958-01-21 Exxon Research Engineering Co Synthetic lubricating compositions and process for their preparation
US2977331A (en) * 1955-10-20 1961-03-28 Upson Co Process of stabilizing cellulose by impregnation with a salt of an organic basic nitrogen compound containing a hydroxyl group and a partial ester of a polyhydric alcohol and polycarboxylic acid and product thereof
US2931837A (en) * 1956-04-13 1960-04-05 Union Carbide Corp Long chain alkoxy-diols
US3048623A (en) * 1957-11-01 1962-08-07 Exxon Research Engineering Co Preparation of complex diester synthetic lubricants
US3381022A (en) * 1963-04-23 1968-04-30 Lubrizol Corp Polymerized olefin substituted succinic acid esters
DE1230511B (en) * 1963-04-29 1966-12-15 Rheinpreussen Ag Lubricating oil for aircraft gas turbines
DE1246921B (en) * 1964-05-05 1967-08-10 Rheinpreussen Ag Lubricating oils for high-speed aircraft with jet or gas turbine propulsion
US3857865A (en) * 1973-08-01 1974-12-31 Emery Industries Inc Ester lubricants suitable for use in aqueous systems
US4122057A (en) * 1974-09-03 1978-10-24 Emery Industries, Inc. Mixed-terminated polyester plasticizers
JPS6176442A (en) * 1984-09-21 1986-04-18 Satoru Matsumoto Production of composite ester
EP0284374A3 (en) * 1987-03-25 1990-12-12 Showa Denko Kabushiki Kaisha Polymerizable vinyl compound having polythioether skeleton, process for preparation thereof and optical element made therefrom
US4909952A (en) * 1989-01-03 1990-03-20 The Lubrizol Corporation Sulfur-containing polymeric polyesters and additive concentrates and lubricating oils containing same
US20010019120A1 (en) 1999-06-09 2001-09-06 Nicolas E. Schnur Method of improving performance of refrigerant systems
US20120302478A1 (en) 2011-05-27 2012-11-29 Exxonmobil Research And Engineering Company Method for producing a two phase lubricant composition
US8623796B2 (en) 2011-05-27 2014-01-07 Exxonmobil Research And Engineering Company Oil-in-oil compositions and methods of making

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1786404A (en) * 1927-10-31 1930-12-23 Young Hoylande Denune Derivative of glycol
US2035528A (en) * 1932-04-16 1936-03-31 Du Pont Synthetic resin
US2073031A (en) * 1935-05-03 1937-03-09 Du Pont Esters of octadecanediol

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1135445B (en) * 1953-07-02 1962-08-30 Exxon Research Engineering Co Process for the preparation of complex esters which can be used as lubricating oils or lubricating oil components
DE1011109B (en) * 1955-12-19 1957-06-27 Geigy Co Ltd lubricant
US3547693A (en) * 1968-01-12 1970-12-15 Eastman Kodak Co Magnetic tape
US6296782B1 (en) 1992-06-03 2001-10-02 Henkel Corporation Polyol ester lubricants for refrigerator compressors operating at high temperatures
US5906769A (en) 1992-06-03 1999-05-25 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5976399A (en) 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US6221272B1 (en) 1992-06-03 2001-04-24 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US6551524B2 (en) 1992-06-03 2003-04-22 Cognis Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US6666985B2 (en) 1992-06-03 2003-12-23 Cognis Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US5820777A (en) 1993-03-10 1998-10-13 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5851968A (en) 1994-05-23 1998-12-22 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants
US6551523B1 (en) 1995-06-07 2003-04-22 Cognis Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids

Also Published As

Publication number Publication date
FR990983A (en) 1951-09-28
US2575195A (en) 1951-11-13

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