US3816313A - Lubricant providing improved fatigue life - Google Patents

Lubricant providing improved fatigue life Download PDF

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Publication number
US3816313A
US3816313A US00307492A US30749272A US3816313A US 3816313 A US3816313 A US 3816313A US 00307492 A US00307492 A US 00307492A US 30749272 A US30749272 A US 30749272A US 3816313 A US3816313 A US 3816313A
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United States
Prior art keywords
silane
composition
condensation polymer
tri
oil
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US00307492A
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English (en)
Inventor
H Szieleit
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Priority to US00307492A priority Critical patent/US3816313A/en
Priority to GB5148373A priority patent/GB1441335A/en
Priority to DE2356269A priority patent/DE2356269A1/de
Priority to JP48127784A priority patent/JPS4981406A/ja
Priority to FR7340934A priority patent/FR2207183A1/fr
Priority to CA185,954A priority patent/CA987653A/en
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Publication of US3816313A publication Critical patent/US3816313A/en
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    • 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
    • C10M155/00—Lubricating compositions characterised by the additive being a macromolecular compound containing atoms of elements not provided for in groups C10M143/00 - C10M153/00
    • C10M155/02—Monomer containing silicon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
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    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
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    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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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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    • 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
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • C10N2010/02—Groups 1 or 11
    • 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

Definitions

  • ABSTRACT J-S-(gl.
  • alkoxysilanes as hydraulic fluids and lubricants. See for example US. Pat. Nos. 2,947,772, 2,985,678 and 2,995,590.
  • the use of homopolymers of vinylalkoxysilanes, polymerized through the vinyl groups, as foam suppressors in concentrations of from 2 to 50 parts per million in hydrocarbon oils is taught in US. Pat. No. 2,862,885.
  • No prior art is known on the use of condensation polymers of alkoxysilanes as additives capable of increasing the fatigue life of a lubricant composition.
  • R is C, to C2 alkyl or C to C alkoxyalkyl, preferably C to C alkyl or alkoxyalkyl, and R is C, to C alkyl or C to C alkoxyalkyl, preferably C to C alkyl or alkoxyalkyl.
  • alkoxyalkyl is meant an ether group that can be represented by C O C wherein the sum of n plus m is 2 to 24 in the case of R and 2 to l2 in the case of R.
  • Representative monomers include dodecyl tributoxy silane, decyl tripropoxy silane, ethoxy propyl triheptoxy silane, octadecyl tripentoxy silane, methoxyamyl trihexoxy silane, hexyl tridecoxyl silane, and octyl tri(methoxypropyl oxy) silane.
  • One method for preparing alkyl trialkoxy silanes is to react one mole of'a commercially available alkyl trichloro silane with 3 moles of an aliphatic alcohol. See for example US. Pat. Nos. 2,947,772 and 2,995,590.
  • the additives of the present invention are condensation polymers of the above-noted alkoxy silanes and can be represented by the formula:
  • x is from about 1 to about 60, or more usually from about 1 to about 40.
  • the additive will comprise a mixture of condensation polymers so that x will represent an average which will usually not be a whole number.
  • the average molecular weights of these additives will be within the range of about 300 to about 30,000. More generally additives with average molecular weight ranging from about 500 to 10,000 will be used.
  • a condensation polymer can be obtained by refluxing an alkyl trialkoxy silane with water in the presence of a strong acid catalyst which is preferably HCl because of its ease of removal from the reaction mixture.
  • a strong acid catalyst which is preferably HCl because of its ease of removal from the reaction mixture.
  • the extent of condensation will depend somewhat on the proportion of water to alkoxy silane; thus in theory one mole of water and two moles of alkoxy silane should give principally the dimer in accordance with the equation:
  • the condensation polymers can also be formed directly by reaction of an appropriate sodium alcoholate with an appropriate halogenated silane.
  • an appropriate sodium alcoholate with an appropriate halogenated silane.
  • one mole of octadecyl trichlorosilane will react with 3 moles of sodium pentoxide at ambient temperature to give a condensation polymer of octadecyl tripentoxy silane with sodium chloride as a by-product.
  • one mole of 3-chloropropyl trichlorosilane will react with 4 moles of sodium pentoxide to give a condensation polymer of pentoxypropyl tripentoxy silane.
  • alkoxy silane condensation polymers employed in the present invention will be used in lubricant compositions in amounts ranging from about 0.01 to about 5 percent by weight based on the total composition.
  • the lubricating oils to which the additives can be added include not only mineral lubricating oils but synthetic oils also.
  • the mineral lubricating oils can be of any preferred type, including those derived from the ordinary paraffinic, naphthenic, asphaltic, or mixed base mineral crude oils by suitable refining methods.
  • the synthetic lubricating oils include not only hydrocarbon oils but also ester oils such as di-2-ethylhexyl sebacate, polyglycols, polycarbonates, glycol esters such as C oxo acid diesters of tetraethylene glycol, and complex esters such as the complex ester formed by reacting one mole of sebacic acid with 2 moles of tetraethylene glycol and 2 moles of 2-ethylhexanoic acid.
  • ester oils such as di-2-ethylhexyl sebacate, polyglycols, polycarbonates, glycol esters such as C oxo acid diesters of tetraethylene glycol, and complex esters such as the complex ester formed by reacting one mole of sebacic acid with 2 moles of tetraethylene glycol and 2 moles of 2-ethylhexanoic acid.
  • additives may also be present, including dyes, pour point depressants, antiwear agents, e.g., tricresyl phosphate, zinc dialkyl dithiophosphates of 3 to 8 carbon atoms, antioxidants such as phenylalpha-naphthylamine, tert. octylpheno] sulfide, bisphenols such as 4,4'-methylene bis(2,6-di tert.
  • dyes e.g., tricresyl phosphate, zinc dialkyl dithiophosphates of 3 to 8 carbon atoms
  • antioxidants such as phenylalpha-naphthylamine, tert. octylpheno] sulfide
  • bisphenols such as 4,4'-methylene bis(2,6-di tert.
  • the average molecular weights varied from about 1,000 to about-3,100.
  • the average molecular weights of condensation polymers prepared by the above procedure ranged from about 560 to about 1,440 if care was taken to dry the reactants. Without such care the molecular weight was found to be considerably higher.
  • Ethoxypropyl Tri iso-Amoxy Silane A mixture of 1.5 ml of 10 percent aqueous HCl and 20 g ETAS (MW2828) was refluxed for 2 hours. The liberated iso-amyl alcohol was distilled off under vacuum (ca 1 to 2 mm Hg). The yield was 11.4 g of the condensed version of ETAS having an average molecular weight of 3,510 i 10 percent. This would correspond to approximately 15.5 units of per molecule.
  • Preparation E Condensation Polymer of Methoxypropyl Tri-iso-Octoxy Silane The procedure of Preparation C was followed, but employing sodium methoxide in place of sodium ethoxide and iso-octyl alcohol in place of iso-amyl alcohol. No determination of the molecular weight of the condensation polymer was made.
  • Lubricating oil blends were prepared using either a base oil X, which was an SAE 10 grade, phenol extracted, dewaxed and hydrofined lube distillate from a Western Canadian crude oil, or a base oil Y, which vwas a refined SAE 10 grade multipurpose hydraulic oil containing a pour point depressant (0.7 vol. percent of a mixture of wax-alkylated naphthalene and methacrylate ester concentrate) an oxidation inhibitor (0.3 wt. percent 2,6-ditert. butyl p-cresol) an antiwear agent (0.5 vol. percent of dihydrocarbyl dithio-phosphate) and a rust inhibitor (0.05 vol.
  • a base oil X which was an SAE 10 grade, phenol extracted, dewaxed and hydrofined lube distillate from a Western Canadian crude oil
  • a base oil Y which vwas a refined SAE 10 grade multipurpose hydraulic oil containing a pour point depressant (0.7 vol. percent of a
  • the blends were prepared by adding, by simple mixing, various concentrations of condensation polymers of alkoxy silanes prepared by the procedures described above. Various concentrations and molecular weights were used in the different blends.
  • Each of the blends as well as each of the base oils was subjected to a test designed to determine the effect of the oils on the fatigue life of bearings. This test is known to correlate with actual field results.
  • the test machine used was a rolling four-ball machine in which three steel balls are allowed to roll freely in a conforming race, while a fourth steel ball which is held firmly in a chuck is pressed on the top of the other three balls and rotated under load.
  • the speed of rotation was 1,600 rpm and the applied load was 887 pounds, which corresponds to an initial maximum contact stress of 1.07 X 10 psi.
  • To run the test the required amount of test oil was poured into the reservoir and the equipment was brought up to the test temperature of F. Each test was run until one of the balls developed a fatigue spall. The excessive vibrations that resulted from the failure of one of the balls actuated a vibration switch which automatically turned off the machine. The longer the time period to failure the greater are the antifatigue properties of the oil being tested.
  • Table l which follows:
  • a lubricating grease is prepared from 76 parts of weight of 12- hydroxystearic acid, ll.5 parts of lithium hydroxide monohydrate, and 908 parts of a solvent-refined mineral lubricating oil of about 460 SUS viscosity measured at 100 F.
  • the 12- hydroxystearic acid is added to about half of the total oil used in the complete grease, the mixture is heated to about l90200 F., the lithium hydroxide is added in the form of an aqueous solution, and the resulting mixture is then heated with stirring to a final temperature of about 380390 F.-Then the remaining portion of the base oil is stirred in and the mixture is cooled to ambient temperature.
  • a lubricating oil composition comprising a major proportion of a hydrocarbon lubricating oil to which has been added from about 0.0l to about 5 percent by weight of the condensation polymer of an alkyl or alkoxy alkyl trialkoxy silane, said condensation polymer being represented by the formula:
  • X is from about l to about 60, R is C to C alkyl, or alkoxy alkyl totaling 2 to 24 carbon atoms, and R is C to C alkyl, or alkoxy alkyl totaling 2 to 12 carbon atoms.
  • composition as defined by claim 1 wherein said condensation polymer has an average molecular weight of from about 300 to about 30,000.
  • composition as defined by claim 1 wherein said condensation polymer is that of octadecyl tri-n-amoxy silane.
  • composition as defined by claim 1 wherein said condensation polymer is that of isoamoxypropyl triisoamoxy silane.
  • composition as defined by claim 1 wherein said condensation polymer is that of methoxypropyl trioctoxy silane.
  • composition as defined by claim 1 wherein said condensation polymer is that of ethoxypropyl triisoamoxy silane.
  • composition as defined by claim 1 which additionally contains a grease thickener.
  • Composition as defined by claim 1 which additionally contains at least one additive selected from the group consisting of an antioxidant, a rust inhibitor and an antiwear additive.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
US00307492A 1972-11-17 1972-11-17 Lubricant providing improved fatigue life Expired - Lifetime US3816313A (en)

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US00307492A US3816313A (en) 1972-11-17 1972-11-17 Lubricant providing improved fatigue life
GB5148373A GB1441335A (en) 1972-11-17 1973-11-06 Lubricant providing fatigue life
DE2356269A DE2356269A1 (de) 1972-11-17 1973-11-10 Schmieroelmischung
JP48127784A JPS4981406A (de) 1972-11-17 1973-11-15
FR7340934A FR2207183A1 (de) 1972-11-17 1973-11-16
CA185,954A CA987653A (en) 1972-11-17 1973-11-16 Lubricant providing improved fatigue life

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2714135A1 (de) * 1976-04-02 1977-10-20 Union Carbide Canada Ltd Schmieroel und seine verwendung
US4335005A (en) * 1980-09-11 1982-06-15 Mobil Oil Corporation Lubricant compositions containing metal antifatigue additives
US4652386A (en) * 1984-10-03 1987-03-24 Bayer Aktiengesellschaft Lubricating oil preparations
WO1991002783A1 (en) * 1989-08-24 1991-03-07 Henkel Corporation Lubricant compositions having improved anti-deposition properties
US5442010A (en) * 1994-10-04 1995-08-15 Dow Corning Corporation Epoxy-terminated polyisobutylene-polydimethylsiloxane compositions
US5507960A (en) * 1994-10-04 1996-04-16 Dow Corning Corporation Method for treating plastic, leather or rubber substrates
US5516832A (en) * 1994-11-03 1996-05-14 Dow Corning Corporation Curable silicone rubber composition
US5629273A (en) * 1994-10-04 1997-05-13 Dow Corning Incorporated Silicone-polybutylene blends
US5662832A (en) * 1994-10-04 1997-09-02 Dow Corning Corporation Blended composition of 2-methylpropenyl-terminated polyisobutylene with polydimethylsiloxane
US5780545A (en) * 1996-03-08 1998-07-14 Eastman Kodak Company Stable release agents
US20070244016A1 (en) * 2006-04-13 2007-10-18 Buck William H Low sap engine lubricant containing silane and zinc dithiophosphate lubricant additive and composition
CN101343590B (zh) * 2002-07-09 2012-02-01 克鲁普顿公司 用于润滑剂和燃料的硅烷添加剂

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1595701A (en) * 1977-06-24 1981-08-19 Castrol Ltd Fluids suitable for use as hydraulic fluids electrical oils heat transfer fluids and refrigerant oils
US7867960B2 (en) 2006-08-31 2011-01-11 Cherron Oronite Company LLC Method for forming tetraoxy-silane derived antiwear films and lubricating oil compositions therefrom
US8067346B2 (en) 2006-08-31 2011-11-29 Chevron Oronite Company Llc Tetraoxy-silane lubricating oil compositions
US8153566B2 (en) 2008-09-30 2012-04-10 Cherron Oronite Company LLC Lubricating oil compositions
US8933001B2 (en) 2010-03-31 2015-01-13 Chevron Oronite Company Llc Method for improving fluorocarbon elastomer seal compatibility
US8901050B2 (en) 2010-03-31 2014-12-02 Chevron Oronite Company Llc Method for improving copper corrosion performance
SG11202011506PA (en) 2018-05-25 2020-12-30 Chevron Oronite Co Method for preventing or reducing low speed pre-ignition in direct injected spark-ignited engines with silane-containing lubricant
CA3101046C (en) 2018-05-25 2024-04-09 Chevron U.S.A. Inc. Method for preventing or reducing low speed pre-ignition in direct injected spark-ignited engines with manganese-containing lubricant

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2714135A1 (de) * 1976-04-02 1977-10-20 Union Carbide Canada Ltd Schmieroel und seine verwendung
US4335005A (en) * 1980-09-11 1982-06-15 Mobil Oil Corporation Lubricant compositions containing metal antifatigue additives
US4652386A (en) * 1984-10-03 1987-03-24 Bayer Aktiengesellschaft Lubricating oil preparations
WO1991002783A1 (en) * 1989-08-24 1991-03-07 Henkel Corporation Lubricant compositions having improved anti-deposition properties
US5047159A (en) * 1989-08-24 1991-09-10 Henkel Corporation Lubricant compositions having improved anti-deposition properties comprising a polyalkylene oxide-modified silicone oil
US5507960A (en) * 1994-10-04 1996-04-16 Dow Corning Corporation Method for treating plastic, leather or rubber substrates
US5442010A (en) * 1994-10-04 1995-08-15 Dow Corning Corporation Epoxy-terminated polyisobutylene-polydimethylsiloxane compositions
US5514419A (en) * 1994-10-04 1996-05-07 Dow Corning Corporation Method for treating plastic, leather or rubber substrates
US5629273A (en) * 1994-10-04 1997-05-13 Dow Corning Incorporated Silicone-polybutylene blends
US5662832A (en) * 1994-10-04 1997-09-02 Dow Corning Corporation Blended composition of 2-methylpropenyl-terminated polyisobutylene with polydimethylsiloxane
US5955536A (en) * 1994-10-04 1999-09-21 Dow Corning Corporation Method for treating plastic, leather or rubber substrates
US5516832A (en) * 1994-11-03 1996-05-14 Dow Corning Corporation Curable silicone rubber composition
US5780545A (en) * 1996-03-08 1998-07-14 Eastman Kodak Company Stable release agents
CN101343590B (zh) * 2002-07-09 2012-02-01 克鲁普顿公司 用于润滑剂和燃料的硅烷添加剂
US20070244016A1 (en) * 2006-04-13 2007-10-18 Buck William H Low sap engine lubricant containing silane and zinc dithiophosphate lubricant additive and composition

Also Published As

Publication number Publication date
GB1441335A (en) 1976-06-30
DE2356269A1 (de) 1974-05-30
JPS4981406A (de) 1974-08-06
FR2207183A1 (de) 1974-06-14
CA987653A (en) 1976-04-20

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