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US3112267A - Lubricating compositions - Google Patents

Lubricating compositions Download PDF

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Publication number
US3112267A
US3112267A US36154A US3615460A US3112267A US 3112267 A US3112267 A US 3112267A US 36154 A US36154 A US 36154A US 3615460 A US3615460 A US 3615460A US 3112267 A US3112267 A US 3112267A
Authority
US
United States
Prior art keywords
acid
oil
lubricating oil
amine
primary
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 - Lifetime
Application number
US36154A
Other languages
English (en)
Inventor
James R Price
Richard G Cunningham
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 USA Inc
Original Assignee
Shell Oil 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 BE604945D priority Critical patent/BE604945A/xx
Priority to AT459261A priority patent/AT229465B/de
Priority to DENDAT1160967D priority patent/DE1160967B/de
Priority to NL134508D priority patent/NL134508C/xx
Priority to NL266093D priority patent/NL266093A/xx
Priority to NL265906D priority patent/NL265906A/xx
Priority to US36154A priority patent/US3112267A/en
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to DK241561AA priority patent/DK104010C/da
Priority to CH690461A priority patent/CH391161A/de
Priority to FR864748A priority patent/FR1303182A/fr
Priority to GB21327/61A priority patent/GB978354A/en
Priority to GB22104/61A priority patent/GB967592A/en
Priority to DES74418A priority patent/DE1148683B/de
Priority to FR865319A priority patent/FR1292599A/fr
Priority to US311618A priority patent/US3160657A/en
Application granted granted Critical
Publication of US3112267A publication Critical patent/US3112267A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • 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
    • 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)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046—Hydroxy ethers
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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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
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/284—Esters of aromatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/285—Esters of aromatic polycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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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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    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • 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
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2209/12—Polysaccharides, e.g. cellulose, biopolymers
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Definitions

  • This invention relates to improved lubricating oil compositions and to a new class of additives therefor.
  • the new additive is an alkali metal-amine halohydro carbyl phosphonate and this additive, although it can be used per se as an oil additive, is particularly compatible with certain oil-soluble sulfur or sulfur-chlorine-containing organic extreme pressure agents and oil-soluble partial esters of polyhydric alcohols and organic carboxylic acids, and the combination produces unexpected and improved results.
  • the new alkali-meta1-amine halohydrocarbyl phosphonate has the general formula:
  • R is a halohydrocarbyl, preferably a middle halogen (C1 or Br) hydrocarbyl such as chloro and/or bromoalkyl, chloro and/ or bromocycloalkyl, chloro and/ or bromoaralkyl or chloro and/ or bromoalkaryl radicals having from 1 to 30 and preferably 1 to carbon atoms
  • X is selected from the group of oxygen and sulfur
  • M is an alkali metal, e.g., Na or K
  • A is an amine, preferably a primary or secondary aliphatic amine which may be straight or branch-chain, preferably the latter.
  • a pre ferred class of compounds represented by Formula I may be represented by the formula:
  • R represents a middle halogen atom, e.g., Cl or Br, 21 hydrogen atom or an alkyl group, the total number of carbon atoms in the alkyl group represented by R being 3, R may be the same as R or a hydrocarbyl radical of up to carbon atoms, preferably when R is not hydrogen or a middle halogen atom, it is an alkyl radical of 2 to 18 carbon atoms, and A represents a higher highly branched aliphatic primary or secondary amine, preferably a C highly branched aliphatic primary amine.
  • the acid portion used to make the mixed metal-amine salts can be prepared by a number of suitable methods such as reported by Arbuzov (Jr. Gen. Chem. USSR; 4,898-900 (1934); Coover (Organic Chemical Bulletin, vol. 23, No. 4, 1951), Barnard (Can. Jr. of Chem, vol. 31, pp. 976983, 1953).
  • Suitable chlorohydrocarbylphosphonic acids for preparing the new alkali metalamine salts include monochloromethylphosphonic acid, 1-monochloroethylphosphonic acid, l-monochloropropylatent phosphonic acid, 1-chloro-l-rnethyl-ethylphosphonic acid, 1-cl11oro2-methy1-propylphosphonic acid, l-chlorobutylphosphonic acid, 1-chloro 1 methyl propylphosphonic acid, trichloromethanephosphinic acid, trichloromethanethiophosphinic vacid, 1,1-dib-romoethanephosphinic acid, 3,3,5-trichlorocyc1ohexanephosphinic acid, 1,1-dich1orohexadecanephosphinic acid, 1,1-dichlorohexadecanephosphinic acid, trichloromethanephosphinic acid, 1,1
  • the amines which can be used to form salts of the above phosphorus acids include highly branched primary aliphatic amines or secondary aliphatic amines of at least 8 carbon atoms.
  • highly branched primary aliphatic amines the tertiary alkyl primary amines are preferred and they can be prepared by any suitable means such as described in the US. Ofice of the Publication Board Report No. 88,843.
  • Other highly branched primary amines can be prepared by converting primary branched chain alcohols as produced by the Oxo process from branched chain olefins as fully described by P. W.
  • tertiary alkyl primary amines containing, as the tertiary alkyl radical, the radical of polyisobutylene, polypropylene and mixture thereof are particularly efiective for the present purpose and they constitute a preferred class of amines for the practice of the invention.
  • 1,1,3,3-tetramethylbutylamine from the amination of diisobutylene
  • 1,1,3,3,5,5- hexamethylhexylamine from triisobutylene
  • 1,1,3,3, 5,5,7,'7-octamethyloctylamine from tetraisobutylene
  • 1,1,3,3,5,S,7,7,9,9-decamethyidecylamine from pentaisobutylene
  • pentaisobutylene are specific preferred amines, which are suitably used individually or as mixtures thereof.
  • primary tertiaryalkylmethylamines such as 2,2,4,4-tetramethyl pentylamine, 2,2,4,4,6,6-hexamethyl heptylamine and the like are suitable.
  • tertiary branched-chain alkyl primary amines which can be used include the C and higher amines of this type mentioned in US. Patents 2,160,058, 2,606,923 and 2,611,782, such as tert.-tridecylamine 12115 as well as isoheptyldiethylcarbinyl amine, isooctylethylpropylcarbinylamine, and the like.
  • Primary amines of this type are commercially available from Rohm and Haas Company under the trade name of Prirnenes, specific products being Primenes 81R, which is a mixture of primary alkylamines containing from about 12 to 15 carbon atoms and Primene JMT, which is a similar tertiary alkylamine mixture containing an average of about 18 to 24 carbon atoms.
  • T able 1 -Properties 'lertiary-Oetylarnine Alkylamine SI-R A1 Allrylamine JM-T A l'rCaHnNHs "I Formula Principally t-CuH25 Principally t-CmH 31 NH: 120 t-C'uHa Nllz Nl'lc t0 t'CZlIi-MNIIL Molecular Weight 129 Principally 1712l3 Principally 269-353. Average Molecular Weight we 1m 301. Specific Gravity, 25O 0.771 O. 81? 0.828. Refractive Index, 25C 1, 423 1. 423 1. 455. Boiling Point (or range) 137143 C. (760 mm.) 590% at 210-227 G. 595% at 275-310 C.
  • the secondary amines which can be used to form salts of the phosphorus acids include secondary amines, preferably aliphatic and cycloaliphatic amines, containing from to 36 carbon atoms.
  • secondary amines preferably aliphatic and cycloaliphatic amines, containing from to 36 carbon atoms.
  • Illustrative of such amines are diamlyamine, dihexylamine, di(2-ethyl-hexyl) amine, dioctylamine, didecylamine, ditetradecylamine, dihexadecylamine, dioctadecylamine, didodecylamine, dibromodioctadecylamine, isopropyloleylamine, diricinoleylamine, butylricinoleylamine, butyl-2-ethylhexylamine, dilaurylamine, methyloleylamine, ethylocty
  • the method of making the mixed alkali metal-amine salts is to first prepare the full amine salt by the methods described in US. Patents 2,777,819, 2,858,332, 2,874,120 or 2,882,228 and thereafter treat the full amine salt in a low boiling solvent such as methanol with an alkali metal such as sodium, potassium or lithium hydroxide, carbonate, alcoholate, e.g. methylate, in an amount sufficient to replace one of the amine groups with an alkali metal.
  • a low boiling solvent such as methanol
  • an alkali metal such as sodium, potassium or lithium hydroxide, carbonate, alcoholate, e.g. methylate
  • the mixture is warmed while stirring and when the reaction is complete the temperature is increased to boil off the solvent, e.g. methanol, and it may he neces sary to strip the product with nitrogen to remove last traces of the solvent.
  • An alternative method of preparing the alkali metal-amine salts such as sodium-amine phosphonate is to dissolve sodium in methanol and add the sodium methylate dropwise while stirring to a full amine salt of an alkyl phosphonic acid at 100200 C. for /2 to 10 hours. The methanol is removed by nitrogen stripping to give a new sodium-amine phosphonate.
  • Example II was prepared in accordance with the procedure of Example I, except that A amine salt of trichloromethylphosphonic acid was used. The final product Na-A amine trichloromethylphosphonate was oil soluble and possessed good extreme pressure properties.
  • alkali metal-amine salts of this invention include mixed salts of Na or K with from primary amines such as t-C H NH t-C H NH to 15 31 1, t-C18H37NH to c,,H,,NH,, dimethyl neopentylcarbinyl amine, tert.tridecylamine, or with secndary amines, e.g., di-Z-ethylhexylamine, di-l-isobutyl- 3-methylbutylamine, didecylamine, dioctadccylamine, isomethanephosphonic acid, trifluoromethancphosphonic acid, tribromomethanephosphonic acid, trichloromethanedithiophosphonic acid, chlorobenzene trichloroinethancphosphinic acid, 1,l-dichloroethanethiophosphonic acid, trichlorobenzenephosphonic acid, trichloromethanc
  • the new alkali metal-amine halohydrocarbyl phosphonates are particularly useful when used in combination with certain classes of additives as previously defined.
  • One class of additives is a sulfurized and/or sulfohalogenated fatty material such as animal, vegetable and marine fats and oils and derivatives thereof. Materials of this type can be prepared by the methods described in US. Patents 2,322,859; 2,454,034; 2,459,717; 2,467,137; 2,614,078; 2,633,825 and 2,701,237.
  • Such materials are sulfurized or sulfo-chlorinated fats, fatty oils of the animal, vegetable and marine type and derivatives thereof, such as sulfurized or sulfo-chlorinated tallow, lard, lanolin, jojoba, oil, rapeseed oil, sperm oil, fatty acids of these fats and oils as well as their esters such as G to C saturated and unsaturated fatty acids, e.g.
  • myristic, stearic, oleic acids polymerized fatty acids such as polymerized linoleic acid or Empol 1022 which is a polymerized fatty acid made by Emery Industries; or esters such as cetyl stearate, cetyl oleate and mixtures thereof; halogenated fats, oils, waxes such as chlorinated paraflin wax, chlorinated tallow, etc. of these materials preferred are the sulfurized and/ or sulfurized-chlorinated sperm oil, lanolin, rapeseed oil, oleic acid, chlorinated paraffin Wax and cetyl olcate as well as mixtures thereof.
  • the other class of materials is an oilsoluble partial ester of polyhydric alcohol and fatty acid having from 832 carbon atoms, preferably fatty acids having 102() carbon atoms, the preferred esters are those derived from polyhydroxy alcohols having a neocarbon atom such as pentaerythritol or derivatives thereof and C1040 unsaturated fatty acids.
  • the acids which can be used to make the partial esters from any of the above alcohols include aliphatic carboxylic acids; cyclo organic carboxylic acids; aromatic carboxylic acids, sulfonic acids and the like.
  • the aliphatic carboxylic acids include the mono and polycarboxylic acids of from 8 to 32, and preferably from 10 to 20, carbon atoms and include saturated and unsaturated fatty acids of from about 10 to 20 carbon atoms such as lauric, stearic, oleic and linoleic acids, as well as aliphatic polycarboxylic acids such as alkenyl succinic acid, alkyl adipic acid and the like.
  • the cyclic carboxylic acids include naphthenic acids, such as cycloexane carboxylic acid, alkylcyclohexane carboxylic acids, alkylcyclopentane carboxylic acid, abietic acid and the like.
  • the aromatic acids include the substituted aromatic carboxylic acids such as bcnzoic, salicyclic phthalic, anthranilic acids, the alkylrated salicyclic and anthranilic acids in which the alkyl radical is from 3 to 20 carbon atoms being preferred ones.
  • esters derived from simple alkanepolyols include glycerol nonooleate, glycerol monostearate, glycerol monoricinoleate, pentaerythritol monocaprylate, pentaerythritol monoand dilaurate, pentaerythitol monoand dioleate, pentaerythritol monoand distear-ate, mono-, di-, and triethylene glycol monooleate, propylene glycol monoricinoleate, monoethylone glycol monooleate, triethylene glycol monostearate, sorbitol monolaurate, mannitol monooleate, mannitol dioleate, sorbitol dioleate, etc.
  • Esters derived from ether-alcohols as described may be prepared by the method described in US. Patent 2,322,- 820.
  • esters which must contain at least one and preferably more than one free hy-droxyl group are sorbitan monoand dioleate, sonbit-an mono and dilaurate, mannitan monoand distearate, mannitan monoand dioleate, sorbitan monoand dipalmitate, sorbitan sesquioleate, sorbitan mononaphthenate, mannitan monolaurate, etc.
  • Esters derived from the sugar alcohols include glucose monoleate, glucose monon'ncinolea'te, sorbose monostearate, frutose monooleate and the like.
  • alkali metal-amine hal-ohydrocarbyl phosphonate alone or in combination with additives as defined are each used in amounts ranging from about 0.5% to about 5% by Weight.
  • compositions of the present invention are meth-acrylate polymers of C alkyl alcohols such as lauryl and/or stearyl methacrylate.
  • Such polymers are commercially available from Rohm and Haas under the trade name of Acryloid 150 or 710.
  • Acryloid 710 is predominantly a copolymer mixture of octyl and lauryl methacrylates having a molecular weight of from about 10,000 to 20,000 or Acryloid 150 which is predominantly a copolymer mixture of cetyl, lauryl and octyl methacrylates having a molecular weight of about 10,00015,000.
  • polymers are sold commercially as 40% concentrate of the polymer in a mineral lubricating oil base, to provide a viscous liquid having a viscosity at 210 F. of from about 600 to 850 centistokes. On an oil-free basis the polymers when used in compositions of this invention vary from 0.001% to 5%.
  • Base oils to which additives of this invention are added may be selected from a variety of natural oils such as paraifinic, naphthenic and mixed base mineral oils having 250 SUS at 210 F.
  • synthetic oils may be used such as polymerized olefins, alkylated aromatics; polyalkyl silicone polymers, e.g., liquid dimethyl silicone polymers, other silicone polymers; H S-adducts of unsaturated ethers and thioethers, e.g., H 8 adduct of diallyl ether; esters, e.-g., di(2-ethylhexyl) sebaeate. Mixtures of natural and synthetic oils can be used.
  • compositions of this invention are:
  • Composition A Percent wt. Na-A monoch-loromethylphosphonate 3.0 Sulfurized sperm oil 4.0 Pentaerythritol monooleate 1.0 Methacrylate polymer (Acryloid 150) 0.2 Mineral lubricating oil (100 SSU at 210 F. neut.) 66.25
  • Composition B Net-A trichloromethylphosphon-ate 3.25 Sulfurized sperm oil 4.0 'Pentaerythritol monooleate 1.0 Methacrylate polymer (Acryloid 150) 0.2 Mineral lubricating oil (100 SSU at 210 F. nent.) 66.25 Bright stock (150 SSU at 210 F.) 25.30
  • composition C Nat-A monochloromethylphosphonate 5 Sulfurized sperm oil 4 Pentaerythritol monooleate 1 Mineral oil (SAE 90) Balance Composition D Na-A monochloromethylphosphonate 5 Sulfurized-chlorinated sperm oil 4 Pentaerythritol monooleate 1 Mineral oil (SAE Balance Composition E- N-a-A monochloromethylphosphonate 5 Mineral oil (SAE 30) Balance Composition 'F K-A monochloromethylphosphonate 3.25 Sulfurized sperm oil 4.0 Pentaerythritol monooleate 1.0 Methaorylate polymer (Acryloid 150) 0.2 Mineral lubricating oil SSU at 210 F. neut.) 66.25 Bright stock (150 SSU at 210 F.) 25.30
  • compositions of the present invention are evidenced by the results as shown in Table II.
  • the tests are CRC L-37 and L-42 described in SAE Jour., March 1960, page 475-480; 325 F. Ordnance Thermal Stability Test, N. T. Meckel and R. D. Quillian, In, A Study of Gear Lubricant Thermal Oxidative Degradation Phenomena, Soc. of Automotive Engrs, Preprint T-38, presented at the SAE Annual Meeting, Detroit, January 11-15, 1960; Continental Oxidation Test described in Anal. Chem, 20, 547, June 1948, and in the 4 Ball Extreme Pressure Tester operated for 1 minute at 1800 r.p.rn. and room temperature, steel on steel.
  • Composition X same as Composition A except that for the mixed N a.A monochloromethylphosphonate ClOHzP OH.Aa
  • compositions of this invention are applicable for high temperature, pressure and speed use as encountered in automotive and truck engines as well as various industrial equipment.
  • a lubricating oil composition consisting essentially of a major amount of lubricating oil and from about 0.05% to about 5% of an alkali metal-C alkylarnine salt of a halo-substituted C hydrocarbyl phosphonic acid.
  • a lubricating oil composition consisting essentially of a major amount of lubricating oil and from about 0.05% to about 5% of an alkali metal-primary C alkylamine salt of a halo-substituted C alkyl phosphonic acid.
  • a mineral lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.05 to about 5% of an alkali metal-primary C alkylamine salt of an a-chloro-substituted C alkyl phosphonic acid.
  • a mineral lubricating oil composition consisting essentially ofa major amount of mineral lubricating oil and from about 0.05 to about 5% of Nta-primary C alkylamine salt of chloromethyl phosphonic acid.
  • a mineral lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.05 to about 5% of a mixed Na-primary PC alkylamine salt of chloromethyl phosphonic acid.
  • a lubricating oil composition consisting essentially of a major amount of lubricating oil and from about 0.05 to about 5% each of (1) an alkali metal-C alkylamine salt of a halo-substituted C hydrooarbyl phosphonic acid, (2) an oil-soluble sulfurized fatty oil and (3) an oil-soluble partial ester of a polyhydric alcohol selected from the group consisting of glycerol and pentaerythritol and an aliphatic carboxylic acid having from 10 to 20 carbon atoms.
  • a lubricating oil composition consisting essentially of a major amount of lubricating oil and from about 0.05 to about 5% each of (1) an alkali metal-primary C alkylamine salt of a halo-substituted C alkyl phosphonic acid, and (2) an oil-soluble sulfurized fatty oil and (3) an oil-soluble partial ester of pentaerythritol and an aliphatic monocarboxylic acid having from to 20 carbon atoms.
  • a mineral lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.05% to about each of (1) an alkali metal-primary C alkylamine salt of an a-chloro-substituted C alkyl phosphonic acid, (2) an oil-soluble sulfurized fatty oil and (3) an oil-soluble partial ester of pentaerythritol and an aliphatic monocarboxylic acid having from 10 to 20 carbon atoms.
  • a mineral lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.05% to about 5% each of Na-primary C al'kylamine salt of chloromethyl phosphonic acid, sulfurized spenrn oil and pentaerythritol monooleate.
  • a mineral lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.05% to about 5% each of a mixed Naprimary t-C alkylamine salt of chloromethyl phosphonic acid, sulfurized spenm oil and pentaerythritol monooleate.
  • the lubricating composition of claim 10 containing a minor amount of a C alkyl methacrylate polymer.
  • a lubricating oil composition consisting essentially of a major amount of a synthetic ester base oil and from about 0.05% to about 5% of an alkali metal-C alkylamine salt of a halo-substituted C hydrocarbyl phosphonic acid.
  • a lubricating oil composition consisting essentially of a major amount of a synthetic ester base oil and from about 0.05% to about 5% of a mixed N-a'primary t-C alkylamine salt of chloromethyl phosphonic acid.

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US36154A 1960-06-15 1960-06-15 Lubricating compositions Expired - Lifetime US3112267A (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
BE604945D BE604945A (nl) 1960-06-15
AT459261A AT229465B (de) 1960-06-15 Schmierend wirkende organische Flüssigkeiten und Verfahren zu ihrer Herstellung
DENDAT1160967D DE1160967B (de) 1960-06-15 Schmiermittel
NL134508D NL134508C (nl) 1960-06-15
NL266093D NL266093A (nl) 1960-06-15
NL265906D NL265906A (nl) 1960-06-15
US36154A US3112267A (en) 1960-06-15 1960-06-15 Lubricating compositions
CH690461A CH391161A (de) 1960-06-15 1961-06-13 Schmiermittel sowie Verfahren zu dessen Herstellung
DK241561AA DK104010C (da) 1960-06-15 1961-06-13 Højtrykssmøremiddel og fremgangsmåde til fremstilling af alkalimetal-aminsalte af halogencarbonhydridphosphonsyrer til anvendelse i smøremidlet.
FR864748A FR1303182A (fr) 1960-06-15 1961-06-13 Compositions lubrifiantes contenant de nouveaux phosphonates et préparation de ces phosphonates
GB21327/61A GB978354A (en) 1960-06-15 1961-06-13 Phosphonates, the preparation thereof, and lubricating compositions containing them
GB22104/61A GB967592A (en) 1960-06-15 1961-06-19 Lubricating compositions
DES74418A DE1148683B (de) 1960-06-15 1961-06-19 Schmiermittel auf der Grundlage von Pentaerythrityl-Estern
FR865319A FR1292599A (fr) 1960-06-15 1961-06-19 Composition d'huile lubrifiante d'ester de pentaérythrityle
US311618A US3160657A (en) 1960-06-15 1963-09-26 Alkali metal-amine salt of halohydrocarbylphosphonic acid

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US36154A US3112267A (en) 1960-06-15 1960-06-15 Lubricating compositions
US3757360A 1960-06-21 1960-06-21
US7192060A 1960-11-28 1960-11-28
US311618A US3160657A (en) 1960-06-15 1963-09-26 Alkali metal-amine salt of halohydrocarbylphosphonic acid

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Cited By (4)

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US3519563A (en) * 1967-10-31 1970-07-07 Chevron Res Thiophosphate salts of aralkylene diamines as antiwear,extreme pressure and oxidation inhibitor agents
DE2044257A1 (de) * 1969-09-08 1971-03-18 Shell Internationale Research Maat schappy N V , Den Haag (Niederlande) Schmierole auf der Grundlage syntheti scher Ester
US3742040A (en) * 1969-07-28 1973-06-26 Stauffer Chemical Co Alkylammonium alkylphosphonamidates
WO1989006683A1 (en) * 1988-01-15 1989-07-27 The Lubrizol Corporation Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives

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Publication number Priority date Publication date Assignee Title
US3308161A (en) * 1962-05-21 1967-03-07 Petrolite Corp Alkali metal-dimethyl dodecyl amine salts of oxyacids of phosphorous and sulfur
GB1054093A (nl) * 1963-06-17
DE2422807C3 (de) * 1974-05-10 1979-05-23 Basf Ag, 6700 Ludwigshafen Salze von Phosphonsäuren
US5021179A (en) * 1990-07-12 1991-06-04 Henkel Corporation Lubrication for refrigerant heat transfer fluids
WO1993024585A1 (en) * 1992-06-03 1993-12-09 Henkel Corporation Polyol ester lubricants for refrigerant heat transfer fluids

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US2382043A (en) * 1938-10-04 1945-08-14 California Research Corp Compounded mineral oil
US2563506A (en) * 1951-08-07 Quaternary ammonium salts of
US2670369A (en) * 1950-09-29 1954-02-23 California Research Corp Phosphonamic acids
US2674616A (en) * 1951-08-18 1954-04-06 Shell Dev Preparation of phosphoruscontaining amine salts
US2849397A (en) * 1955-12-28 1958-08-26 California Research Corp Silver phosphates as wear-reducing agents
US2858332A (en) * 1956-08-17 1958-10-28 Shell Dev Amine salts of monohaloalkylphosphonic acids
US2874120A (en) * 1956-08-17 1959-02-17 Shell Dev Lubricating oil compositions
US2882228A (en) * 1955-06-20 1959-04-14 Shell Dev Metal working lubricants
US2889282A (en) * 1956-09-17 1959-06-02 Shell Dev Lubricating oil compositions

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US2286792A (en) * 1940-02-24 1942-06-16 Eastman Kodak Co Yarn conditioning process and composition therefor
DE865899C (de) * 1943-02-06 1953-02-05 Basf Ag Verfahren zur Gewinnung von Gemischen von Estern des Pentaerythrits mit organischen Saeuren
US2777819A (en) * 1954-04-27 1957-01-15 Shell Dev Lubricating compositions
NL102109C (nl) * 1955-09-26

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US2563506A (en) * 1951-08-07 Quaternary ammonium salts of
US2382043A (en) * 1938-10-04 1945-08-14 California Research Corp Compounded mineral oil
US2670369A (en) * 1950-09-29 1954-02-23 California Research Corp Phosphonamic acids
US2674616A (en) * 1951-08-18 1954-04-06 Shell Dev Preparation of phosphoruscontaining amine salts
US2882228A (en) * 1955-06-20 1959-04-14 Shell Dev Metal working lubricants
US2849397A (en) * 1955-12-28 1958-08-26 California Research Corp Silver phosphates as wear-reducing agents
US2858332A (en) * 1956-08-17 1958-10-28 Shell Dev Amine salts of monohaloalkylphosphonic acids
US2874120A (en) * 1956-08-17 1959-02-17 Shell Dev Lubricating oil compositions
US2889282A (en) * 1956-09-17 1959-06-02 Shell Dev Lubricating oil compositions

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3519563A (en) * 1967-10-31 1970-07-07 Chevron Res Thiophosphate salts of aralkylene diamines as antiwear,extreme pressure and oxidation inhibitor agents
US3742040A (en) * 1969-07-28 1973-06-26 Stauffer Chemical Co Alkylammonium alkylphosphonamidates
DE2044257A1 (de) * 1969-09-08 1971-03-18 Shell Internationale Research Maat schappy N V , Den Haag (Niederlande) Schmierole auf der Grundlage syntheti scher Ester
WO1989006683A1 (en) * 1988-01-15 1989-07-27 The Lubrizol Corporation Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives
US4957651A (en) * 1988-01-15 1990-09-18 The Lubrizol Corporation Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives

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NL266093A (nl)
CH391161A (de) 1965-04-30
NL265906A (nl)
US3160657A (en) 1964-12-08
DE1148683B (de) 1963-05-16
NL134508C (nl)
BE604945A (nl)
DE1160967B (de) 1964-01-09
AT229465B (de)

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