GB953542A - Oil-soluble thioether compounds and lubricating oil compositions containing them - Google Patents

Oil-soluble thioether compounds and lubricating oil compositions containing them

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Publication number
GB953542A
GB953542A GB23097/60A GB2309760A GB953542A GB 953542 A GB953542 A GB 953542A GB 23097/60 A GB23097/60 A GB 23097/60A GB 2309760 A GB2309760 A GB 2309760A GB 953542 A GB953542 A GB 953542A
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United Kingdom
Prior art keywords
formula
hydrogen
oil
radical
carbon atom
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
GB23097/60A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US824796A external-priority patent/US3189547A/en
Priority claimed from US8498A external-priority patent/US3112268A/en
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority claimed from US77781A external-priority patent/US3198737A/en
Publication of GB953542A publication Critical patent/GB953542A/en
Expired legal-status Critical Current

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
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    • 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
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
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    • 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
    • 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
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • 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
    • C10N2040/02—Bearings
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Lubricants (AREA)

Abstract

The invention comprises oil-soluble thioether compounds of the formula (Z-(CH2)n-S)n3-(R)-COO-(R11-X) n1-(R1-O)n2-CO.(R) -(S-(CH2)n-Z)n3 wherein R is an aliphatic radical having at least 8 carbon atoms and optionally containing a hydroxyl group, R1 and R11 are C2-8 alkylene radicals, X is oxygen or sulphur, n1, n2 and n3 are integers of at least 1, n is an integer of from 1-4 and Z is -OR111 or -COOR111, R111 being hydrogen or a C1-4 alkyl radical, and in which not more than one -S-(CH2)n-Z group is attached to any carbon atom, and in which there is adjacent to each carbon atom bearing an -S-(CH2)n-Z group a carbon atom bearing at least one hydrogen atom. The thioether derivatives are prepared by the reaction of a di-ester of a long-chain unsaturated fatty acid and a polyoxyalkylene diol or an analogous sulphur containing diol of formula: <FORM:0953542/C2/1> with a mercapto compound of formula: HS(CH2)nZ where R1, R11, X, Z, n, n1 and n2 are as defined above and wherein R1 is an aliphatic radical containing at least 8 carbon atoms and, optionally, a hydroxyl group, at low temperatures in the presence of a free-radical catalyst and a non-reactive solvent. The diester starting materials of the formula: <FORM:0953542/C2/2> are prepared by conventional esterification of the diol of formula: HO - (R11 - X)n1 - (R1 - O)n2H with an acid R1.COOH, the symbols being as defined above. Examples are given. The novel compounds are used as lubricating oil additives (see Division C5). 2-Thia-alkyl-phosphono compounds of the formula: <FORM:0953542/C2/3> wherein R stands for a hydrocarbyl radical having at least 6 carbon atoms, the R1's stand for hydrogen, hydrocarbyl or cationic groups, R2 stands for hydrogen or a C1-4 alkyl radical and the X's stand for oxygen or sulphur, may be prepared by the method of Specification 904,968 and are used as lubricating oil additives (see Division C5). Examples are given. Specifications 651,712 and 863,339 also are referred to.ALSO:Lubricating oil compositions comprise synthetic oils or natural hydrocarbon oils and compounds of the formula (Z-CH2)n-S)n3(R)-COO-(R11-X)n1 -(R1-O)n2-CO.(R)-(S-(CH2)n-Z)n3\t wherein R is an aliphatic radical having at least 8 carbon atoms and optionally containing a hydroxyl group, R1 and R11 are C2- 8 alkylene radicals, X is oxygen or sulphur, n1, n2 and n3 are integers of at least 1, n is an integer of from 1-4 and Z is -OR111 or -COOR111, R111 being hydrogen or a C1- 4 alkyl radical, and wherein not more than one -S-(CH2)n-Z group is attached to any carbon atom, and wherein there is adjacent to each carbon atom bearing an -S-(CH2)n-Z group a carbon atom bearing at least one hydrogen atom (see Division C2). The compositions may additionally contain compounds of the formula <FORM:0953542/C3/1> wherein R stands for a hydrocarbyl radical having at least 6 carbon atoms which may be chlorinated, the R1's stand for hydrogen, hydrocarbyl or cationic (e.g. metal or amine) groups, R2 stands for hydrogen or a C1- 4 alkyl radical and the X's stand for oxygen or sulphur (see Division C2). The lubricating oil may be any known type of natural hydrocarbon oil, examples being given, or a synthetic oil which may be a polymerized olefin, alkylated aromatic, isomerized wax, a copolymer of alkylene glycol and alkylene oxides, and ethers thereof, organic diesters. Blends of hydrocarbon oil with castor oil, lard oil, synthetic oils as above, and/or silicone polymers are also mentioned. Optional additives mentioned include silicone antifoaming agents, phenolic antioxidants, polyacrylate esters and viscosity-index improvers, and lauric or oleic acid as oiliness agents. Specifications 651,712, 863,339, and 904,968 are referred to.
GB23097/60A 1959-07-03 1960-07-01 Oil-soluble thioether compounds and lubricating oil compositions containing them Expired GB953542A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US824796A US3189547A (en) 1959-07-03 1959-07-03 Lubricating compositions
US8498A US3112268A (en) 1960-02-15 1960-02-15 Lubricating oil composition
US77781A US3198737A (en) 1960-12-23 1960-12-23 Lubricating compositions and additives therefor

Publications (1)

Publication Number Publication Date
GB953542A true GB953542A (en) 1964-03-25

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Family Applications (2)

Application Number Title Priority Date Filing Date
GB23097/60A Expired GB953542A (en) 1959-07-03 1960-07-01 Oil-soluble thioether compounds and lubricating oil compositions containing them
GB45910/61A Expired GB1002435A (en) 1959-07-03 1961-12-21 Oil-soluble sulphoxy compounds and lubricating oil compositions comprising them

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB45910/61A Expired GB1002435A (en) 1959-07-03 1961-12-21 Oil-soluble sulphoxy compounds and lubricating oil compositions comprising them

Country Status (4)

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BE (2) BE611857A (en)
DE (2) DE1144426B (en)
GB (2) GB953542A (en)
NL (2) NL272806A (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1103762A (en) * 1954-04-23 1955-11-07 Roussel Uclaf New derivatives of thioglycolic acid and their preparation process

Also Published As

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DE1144426B (en) 1963-02-28
GB1002435A (en) 1965-08-25
BE592498A (en)
BE611857A (en)
NL253315A (en)
DE1234905B (en) 1967-02-23
NL272806A (en)

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