US3198739A - Lubricants and polymeric additives therefor - Google Patents

Lubricants and polymeric additives therefor Download PDF

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Publication number
US3198739A
US3198739A US71403A US7140360A US3198739A US 3198739 A US3198739 A US 3198739A US 71403 A US71403 A US 71403A US 7140360 A US7140360 A US 7140360A US 3198739 A US3198739 A US 3198739A
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US
United States
Prior art keywords
methacrylate
copolymer
vinyl
oil
stearyl
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
US71403A
Inventor
Harry F Richards
Jr Stephen A Herbert
Robert J Moore
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
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US71403A priority Critical patent/US3198739A/en
Priority to GB41977/61A priority patent/GB947800A/en
Priority to DES76807A priority patent/DE1237721B/en
Priority to FR879828A priority patent/FR1306897A/en
Application granted granted Critical
Publication of US3198739A publication Critical patent/US3198739A/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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/005—Macromolecular compounds, e.g. macromolecular compounds composed of alternatively specified monomers not covered by the same main group
    • 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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/08—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
    • 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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—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
    • C10M145/12—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 monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
    • 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
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
    • C10M151/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • 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
    • C10M153/00—Lubricating compositions characterised by the additive being a macromolecular compound containing phosphorus
    • C10M153/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • 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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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
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    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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    • C10M2217/026—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrile group
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
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    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
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    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
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    • C10M2223/047—Thioderivatives not containing metallic elements
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    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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    • 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
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    • C10N2040/13—Aircraft turbines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines
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    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/17—Electric or magnetic purposes for electric contacts

Definitions

  • Polymers of this type may be represented by the Formula I where R and R are alkyl radicals as defined above, Y may be a C alkyl radical or a polar radical such as an ester, amide, amine, or phosphate radical or the like, m and m; are Whole numbers of at least 2 each and u may be zero or a Whole number, the ratio of m to m may vary from 1:10 to :1, preferably from 5:1 to 2:1 and the ratio of m+m to n when n is a whole number may vary from 10:1 to 5:1, respectively.
  • the molecular weight of the polymer varies from about one thousand to about one million, preferably from 10,000 to 500,000.
  • the first polymerizable monomer group includes acrylic and alkacrylic esters of aliphatic alcohols of at least 8 carbon atoms, preferably of from 10 to 20 carbon atoms, and include, inter alia, decyl acrylate, lauryl acrylate, stearyl acrylate, eicosanyl acrylate, docosanyl acrylate, decyl methacrylate, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate, and the like, and mixtures thereof.
  • the other polymerizable group includes omega-hydroxyesters of acrylic or alkacrylic acid and dihydroxy alkanes which may be straight or branch-chain, preferably alpha,
  • vinyl ethers vinyl dodecyl ether, vinyl tridecyl ether, vinyl tetracosyl ether, vinyl hexacosyl ether; allyl esters or ethers, allyl stearate, allyl dodecyl ether; amido esters, e.g., N-lauryl methacrylamide, N-stearyl methacrylamide, N,N'-di-.stearyl methacrylamide; vinylpyridines, e.g., 4- vinylpyridine, 2-methyl-5-vinylpyridine, vinylpyrrolidone, vinyl phosphonates and allyl phosphates, e.g., tn'methallyl phosphate, bis-chloroethyl vinyl phosphonate and and mixtures thereof.
  • vinylpyridines e.g., 4- vinylpyridine, 2-methyl-5-vinylpyridine, vinylpyrrolidone, vinyl phosphonates and allyl phosphates, e
  • the polymerization may be effected in the presence of a substantially inert liquid and in the presence of an oxygen-yielding catalyst at a temperature in the range of 50 to C., preferably between 6090 C.
  • Suitable liquid reaction media are various classes of hydrocarbons or their mixtures which are liquid and substantially inert under the polymerization conditions of the present process.
  • Certain classes of aliphatic hydrocarbons can be employed as'a liquid hydrocarbon reaction medium in the present process.
  • various saturated hydrocarbons alkanes and cycloalkanes
  • Either pure alkanes or cycloalkanes or commercially available mixtures, freed of catalyst poisons, may be employed.
  • liquid or liquefied alkanes such as n-pentane, n-hexane, 2,3-dimethylbutane, n-octane, isooctane (2,2,4- trimethylpentane), n-decane, n-dodecane, cyclohexane, methylcyclohexane, dimethylcyclopentane, ethylcyclohexane, decalin, methyldecalins, dimethyldecalins and the like.
  • alkanes such as n-pentane, n-hexane, 2,3-dimethylbutane, n-octane, isooctane (2,2,4- trimethylpentane), n-decane, n-dodecane, cyclohexane, methylcyclohexane, dimethylcyclopentane, ethylcyclohexane
  • aromatic hydrocarbon series particularly the mononuclear aromatic hydrocarbons, viz., benzene, toluene, xylenes, mesitylene and xylene-p-cymene mixtures can also be employed.
  • aromatic hydrocarbons as ethylbenzene, isopropylbenzene, sec-butylbenzene, t-butylbenzene, ethyltoluene, ethylxylenes, hemimellitene, pseudocumene, prehnitene, isodurene, diethylbenzenes, isoamylbenzene and the like.
  • Suitable aromatic hydrocarbon fractions can be obtained by the selective extraction of aromatic naphthas from hydroforming operations as distillates or bottoms, from cyclo stock fractions of cracking operations, etc.
  • alkyl naphthalenes which are liquid under the polymerization reaction con recovered and the copolymer exhibited excellent detergent properties.
  • acry a VIII do ..do Triallyl phosphate" Heptene. do 80 100,000 IX w-Hydlrotxyamyl methdo Vinyl pyrrolidone..- Benzene do 80 200, 000
  • an oil-soluble copolymer of stearyl methacrylate/ 2 methyl-S-vinylpyridine/ omega hydroxyamyl methacrylate having a moiecular weight of 100,000 was
  • additional improvements with respect to oxidation stability and scufiing inhibition can be imparted to the oil compositions containing the copolymers of this invention by incorporating small amounts (0.01%- 2%, preferably 0.1%-1%) of phenolic antioxidants such as alkylphenols, e.g., 2,6-ditertbutyl-4-methylphenol or p,p'-methylene bisphenols such as 4,4-rnethylene bis (2,6-ditertbutylphenol) or arylamines such as phenylalpha-naphthylamine and mixtures thereof.
  • phenolic antioxidants such as alkylphenols, e.g., 2,6-ditertbutyl-4-methylphenol or p,p'-methylene bisphenols such as 4,4-rn
  • Anti-scuifing agents include organic phosphites, phosphates, phosphonates and their thio-derivatives, such as C alkyl phosphites, or phosphonates, e.g., diand tributyl, octyl, lauryl, stearyl, cyclohexyl, benzyl, cresyl, phenyl, phosphites or phosphates, as well as their thio-derivatives, P S -terpene reaction product, e.g., P S -pine oil reaction product and alkali metal salts thereof such as a potassium salt of a P S -terpene reaction product, phosphonates such as dibutyl methanephosphonate, dibutyl trichloromethanephosphonate, dibutyl monochloromethanephosphonate, dibutyl chlorobenzenephosphonate, and the like.
  • the polymeric additives of this invention improve various mineral oil products by the incorporation of a minor amount (0.01% to 5%, preferably 0.1% to 3% by weight) of the additive.
  • they may be used to improve transformer oils, turbine oils, mineral lubricating oils, industrial oils and the like.
  • lubricating oils range from SAE 5W viscosity grade .to SAE 140 grade and are derived from parafiinic, naphthenic or asphaltic base crudes.
  • Representative oils are refined high viscosity index mineral oils having a viscosity of F of 100 to 250 SUS.
  • a typical mineral lubricating oil (X) of this type had the following properties:
  • Lubricating compositions of this invention are particularly applicable for high temperature, high speed use as in aviation engines, automotive engines, truck engines
  • Composition A Percent wt. 11 d 1
  • a mineral lubricating oil composition consisting es- 1e c 01 mer 2 sentially of a major amount of mineral lubricating oil Mineral lubricgfig on 6 Balance and from about 0.01% to by weight of an oil-soluble Com osition copolymer of a C1240 alkyl methacrylate and an ester of g 1e Co 01 mar 2 methacrylic acid and an alpha, omega C alkanediol in Minergl z z oil Balance the ratio of 1:10 to 10: 1, respectively, said copolyiner hav- Com osition ing a molecular weight of from 10,000 to 500,000.
  • a mineral lubricating oil composition consisting es- Minergl lubricagny on Balance sentially of major amount of mineral lubricating Oil and Com osition g 1 from about 0.01% to 5% by weight of an oil-soluble g 1e co olymer 2 copolymer of a C1240 alkyl methacrylate and an ester of Mineral lubricgfing oil Balance methacrylic acid and 1,5-pentanediol in the ratio of 1:10 Composition to 10:1, respectively, said copolymer having a molecular Example copolymer 3 weight of from 10,000 to 500,000.
  • a mineral lubricating oil composition consistlng es- Mineml lubricating (aviation oil 65 sentially of a major amount of mineral lubricating oil grade) Balance and from about 0.01% to 5% by weight of an oil-soluble comnosifion copolymer of stearyl methacrylate and an ester of methajixamnle I'copdymer 5 crylic acid and 1,5-pentanediol in the ratio of 1:10 to 4 4, methy1ene his, g ';gg g gfl ggf 0 5 10:1, respectively, said copolymer having a molecular Tricresyl phosphate weight of from 10,000 to 500,000.
  • a mineral lubricating oil composition consisting esi "f "i sentially of a major amount of mineral lubricating oil in order to demonstrate the utility and nnproved propand from about 0.01% to 5% by weight of an oil-soluble erties of this invention, the c0mpos1t1ons identified in copolymer of stearyl methacrylate, lauryl methacrylate, Table I were tested in the Chevrolet V8 Sludgmg Test, an ester of methacrylic acid and 1,5-pentanediol in the modified EX-3 test described in CRC Progress Report ratio of 1:10 to 10:1, respectively, said copolymer having No. 3, June 1, 1957, and the results were as follows: a molecular weight of from 10,000 to 500,000.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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Description

United States Patent 3 198,739 LUBRECANTS ANDPULYMERIC ADDITIVES THEREFOR Harry F. Richards, Concord, alif., Stephen A. Herbert, Jr., Weston, Conn, and Robert 3. Moore, Orinda, Calih, assignors to Shell Gil Company, New York, N.Y., a corporation of Delaware No Drawing. Fiied Nov. 25, 1960, Ser. No. 71,403 4 Claims. (Cl. 252-56) This invention relates to improved mineral oil lubricating compositions and to an improved oil-soluble polyhydroxy-carboxylate copolymer therefor.
It is known that certain nitrogen-containing polymer compounds such as the commercial additives LOA-564 and 565 of Du Pont or Rohm and Haas 900 Series Acryloids such as Acryloid 917 or 966 as well as others, are good detergent additives for lubricating oil compositions. Such detergent nitrogen-containing polymeric additives lack wear-inhibiting properties and therefore oils which contain them must be supplemented with wear inhibitors or extreme pressure agents, etc. These materials and the acidic materials formed during engine operation tend to interact with the polymeric nitrogen-containing detergents, resulting in sludge and corrosion.
It is an object of the present invention to provide an improved oil-soluble detergent copolymer. Another object of the invention is to provide a lubricating oil composition possessing good detergent and antisluding properties. Still another object of the invention is to provide a lubricating oil composition containing a novel oxygencontaining copolymer which possesses good detergent and anti-sludging properties. Other objects in accordance with the invention will be apparent hereinafter.
It has now been discovered that these and other objects of the present invention may be accomplished by a new and novel copolymer having essentially a long linear hydrocarbon backbone chain and attached thereto, in a random or uniform fashion, two essential groups, the first being an oil-solubilizing ester group COOR where R is a C1040 alkyl radical, preferably a C alkyl radical, and the second being a -COOROH group where R is a C alkyl radical. Polymers of this type may be represented by the Formula I where R and R are alkyl radicals as defined above, Y may be a C alkyl radical or a polar radical such as an ester, amide, amine, or phosphate radical or the like, m and m; are Whole numbers of at least 2 each and u may be zero or a Whole number, the ratio of m to m may vary from 1:10 to :1, preferably from 5:1 to 2:1 and the ratio of m+m to n when n is a whole number may vary from 10:1 to 5:1, respectively. The molecular weight of the polymer varies from about one thousand to about one million, preferably from 10,000 to 500,000.
The first polymerizable monomer group includes acrylic and alkacrylic esters of aliphatic alcohols of at least 8 carbon atoms, preferably of from 10 to 20 carbon atoms, and include, inter alia, decyl acrylate, lauryl acrylate, stearyl acrylate, eicosanyl acrylate, docosanyl acrylate, decyl methacrylate, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate, and the like, and mixtures thereof.
The other polymerizable group includes omega-hydroxyesters of acrylic or alkacrylic acid and dihydroxy alkanes which may be straight or branch-chain, preferably alpha,
3,198,739 Patented Aug. 3, 1965 decanoate, vinyl myristate, vinyl pentadecanoate, Vinyl.
palmitate, vinyl margarat'e, vinyl stearate, vinyl nonadecanoate, vinyl arachidate,-vinyl behenate, vinyl 4,5,6-trimethyldodecanoate, vinyl 6,8,9-triethyltridecanoate, vinyl IZ-hydroxystearate, vinyl 9,10-dihydroxystearate, vinyl chlorostearate, vinyl cyanostearate, vinyl acetylstearate;. vinyl ethers, vinyl dodecyl ether, vinyl tridecyl ether, vinyl tetracosyl ether, vinyl hexacosyl ether; allyl esters or ethers, allyl stearate, allyl dodecyl ether; amido esters, e.g., N-lauryl methacrylamide, N-stearyl methacrylamide, N,N'-di-.stearyl methacrylamide; vinylpyridines, e.g., 4- vinylpyridine, 2-methyl-5-vinylpyridine, vinylpyrrolidone, vinyl phosphonates and allyl phosphates, e.g., tn'methallyl phosphate, bis-chloroethyl vinyl phosphonate and and mixtures thereof.
The polymerization may be effected in the presence of a substantially inert liquid and in the presence of an oxygen-yielding catalyst at a temperature in the range of 50 to C., preferably between 6090 C.
Suitable liquid reaction media are various classes of hydrocarbons or their mixtures which are liquid and substantially inert under the polymerization conditions of the present process. Certain classes of aliphatic hydrocarbons can be employed as'a liquid hydrocarbon reaction medium in the present process. Thus may be employed various saturated hydrocarbons (alkanes and cycloalkanes) which are liquid under the polymerization reaction conditions and which do not crack substantially under the reaction conditions. Either pure alkanes or cycloalkanes or commercially available mixtures, freed of catalyst poisons, may be employed. For example, we may employ straight run naphthas or kerosenes containing alkanes and cycloalkanes. Specifically, we may employ liquid or liquefied alkanes such as n-pentane, n-hexane, 2,3-dimethylbutane, n-octane, isooctane (2,2,4- trimethylpentane), n-decane, n-dodecane, cyclohexane, methylcyclohexane, dimethylcyclopentane, ethylcyclohexane, decalin, methyldecalins, dimethyldecalins and the like.
Members of the aromatic hydrocarbon series, particularly the mononuclear aromatic hydrocarbons, viz., benzene, toluene, xylenes, mesitylene and xylene-p-cymene mixtures can also be employed. In addition, we may employ such aromatic hydrocarbons as ethylbenzene, isopropylbenzene, sec-butylbenzene, t-butylbenzene, ethyltoluene, ethylxylenes, hemimellitene, pseudocumene, prehnitene, isodurene, diethylbenzenes, isoamylbenzene and the like. Suitable aromatic hydrocarbon fractions can be obtained by the selective extraction of aromatic naphthas from hydroforming operations as distillates or bottoms, from cyclo stock fractions of cracking operations, etc.
'Also may be employed certain alkyl naphthalenes which are liquid under the polymerization reaction con recovered and the copolymer exhibited excellent detergent properties.
EXAMPLE V In a benzene solution containing 0.2% alpha,alpha'- azodiisobutyronitrile 2 mols of stearyl methacrylate, 1 mol of bischloroethylvinyl phosphonate and 1 mol of omega-hydroxyamyl methacrylate were added and the mixture was heated for 24 hours at 80 C. At the end of the reaction time an oil-soluble copolymer of stearyl methacrylate/bis chloroethylvinyl phosphonate/omegahydroxyamyl methacrylate havin a molecular weight of 150,000 was recovered and the copolymer exhibited excellent detergent properties.
, Following the above procedure, the following copolymers were prepared:
Omega-hydroxy 05-1 05-20 alkyl aerylate Temp., Molecular Example acrylate ester ester Optional monomer Solvent Catalyst 0. weight of polymer VI w-F ydroxyamyl acrystearyl methacrylate.. Benzene Ditertbutyl peroxide 90 250,000
Y a e. VII w-Hydlrotiyhexyl methd0 -d0 a, a-Azodiisobutyronitrile.. 80 150, 000
acry a VIII do ..do Triallyl phosphate" Heptene. do 80 100,000 IX w-Hydlrotxyamyl methdo Vinyl pyrrolidone..- Benzene do 80 200, 000
nary a e. X do Lauryl methacrylate" Vinyl stearate 1o do 90 250,000
The following examples are illustrative of the present invention.
EXAMPLEI In a benzene solution containing 0.2% alpha,a1pha'- azodiisobutyronitrile 2 mols of stearyl methacrylate and 1 mol of omega-hydroxyamyl methacrylate were added and the mixture was heated for 24 hours at 80 C. At the end of the reaction time an oil-soluble copolymer of stearyl methacrylate/ omega hydroxyamylmethacrylate having a molecular weight of 155,000 was recovered and the copolymer exhibited excellent detergent properties.
EXAMPLE II In a benzene solution containing 0.2% alpha,a1pha'- azodiisobutyronitrile 1.1 mols of stearyl methacrylate, 1.9 mols of lauryl methacrylate and 1 mol of omegahydroxyamyl methacrylate were added and the mixture was heated for 24 hours at 80 C. At the end of the reaction time an oil-soluble copolymer of stearyl methacrylate/omega-hydroxyamyl methacrylate having a molecular weight of 400,000 was recovered and the copolymer exhibited excellent detergent properties.
EXAMPLE III In a benzene solution containing 0.2% alpha,alpha'- azodiisobutyronitrile 2 mols of stearyl methacrylate and 1 mol of 1,B-dirnethyl-omega-hydroxyamyl methacrylate were added and the mixture was heated for 24 hours at 80 C. At the end of the reaction time an oil-soluble copolymer of stearyl methacrylate/1,3-dimethyl-omega hydroxyarnyl methacrylate having a molecular weight of 155,000 was recovered and the copolymer exhibited excellent detergent properties.
EXAMPLE IV In a benzene solution containing 0.2% alpha,alpha- :azodiisobutyronitrile 2 mols of stearyl methacrylate, 1 mol Z-rnethyl-S-Vinylpyridine and 1 mol of omegahydroxyamyl methacrylate were added and the mixture was heated for 24 hours at 80 C. At the end of the reaction time an oil-soluble copolymer of stearyl methacrylate/ 2 methyl-S-vinylpyridine/ omega hydroxyamyl methacrylate having a moiecular weight of 100,000 was When desired, additional improvements with respect to oxidation stability and scufiing inhibition can be imparted to the oil compositions containing the copolymers of this invention by incorporating small amounts (0.01%- 2%, preferably 0.1%-1%) of phenolic antioxidants such as alkylphenols, e.g., 2,6-ditertbutyl-4-methylphenol or p,p'-methylene bisphenols such as 4,4-rnethylene bis (2,6-ditertbutylphenol) or arylamines such as phenylalpha-naphthylamine and mixtures thereof. Anti-scuifing agents include organic phosphites, phosphates, phosphonates and their thio-derivatives, such as C alkyl phosphites, or phosphonates, e.g., diand tributyl, octyl, lauryl, stearyl, cyclohexyl, benzyl, cresyl, phenyl, phosphites or phosphates, as well as their thio-derivatives, P S -terpene reaction product, e.g., P S -pine oil reaction product and alkali metal salts thereof such as a potassium salt of a P S -terpene reaction product, phosphonates such as dibutyl methanephosphonate, dibutyl trichloromethanephosphonate, dibutyl monochloromethanephosphonate, dibutyl chlorobenzenephosphonate, and the like. The full esters of pentavalent phosphorous acids such as triphenyl, tricresyl, trilauryl and tristearyl ortho-phosphates or potassium salt of P S -terpene reaction product are preferred.
The polymeric additives of this invention improve various mineral oil products by the incorporation of a minor amount (0.01% to 5%, preferably 0.1% to 3% by weight) of the additive. Thus, they may be used to improve transformer oils, turbine oils, mineral lubricating oils, industrial oils and the like. Suitably such lubricating oils range from SAE 5W viscosity grade .to SAE 140 grade and are derived from parafiinic, naphthenic or asphaltic base crudes. Representative oils are refined high viscosity index mineral oils having a viscosity of F of 100 to 250 SUS. A typical mineral lubricating oil (X) of this type had the following properties:
Gr. API, 60/60 F 32 Flash, F. 370 Viscosity Index (Dean and Davis) 93 Viscosity, SUS at 100 F. 103
5 The following non-ash compositions are representative of this aspect of the invention.
Lubricating compositions of this invention are particularly applicable for high temperature, high speed use as in aviation engines, automotive engines, truck engines Composition A: Percent wt. 11 d 1 Example I copolymer 2 ustna zi 5 e c arm as our mven ion: i sgiil g 011 (X) Balance 1. A mineral lubricating oil composition consisting es- 1e c 01 mer 2 sentially of a major amount of mineral lubricating oil Mineral lubricgfig on 6 Balance and from about 0.01% to by weight of an oil-soluble Com osition copolymer of a C1240 alkyl methacrylate and an ester of g 1e Co 01 mar 2 methacrylic acid and an alpha, omega C alkanediol in Minergl z z oil Balance the ratio of 1:10 to 10: 1, respectively, said copolyiner hav- Com osition ing a molecular weight of from 10,000 to 500,000.
g 1e Co 01 2 2. A mineral lubricating oil composition consisting es- Minergl lubricagny on Balance sentially of major amount of mineral lubricating Oil and Com osition g 1 from about 0.01% to 5% by weight of an oil-soluble g 1e co olymer 2 copolymer of a C1240 alkyl methacrylate and an ester of Mineral lubricgfing oil Balance methacrylic acid and 1,5-pentanediol in the ratio of 1:10 Composition to 10:1, respectively, said copolymer having a molecular Example copolymer 3 weight of from 10,000 to 500,000. 4 4, methy1ene bis 2 ig f g zg gg g' s 1 3. A mineral lubricating oil composition consistlng es- Mineml lubricating (aviation oil 65 sentially of a major amount of mineral lubricating oil grade) Balance and from about 0.01% to 5% by weight of an oil-soluble comnosifion copolymer of stearyl methacrylate and an ester of methajixamnle I'copdymer 5 crylic acid and 1,5-pentanediol in the ratio of 1:10 to 4 4, methy1ene his, g ';gg g gfl ggf 0 5 10:1, respectively, said copolymer having a molecular Tricresyl phosphate weight of from 10,000 to 500,000. Mineral lubricating 5 7i Balane 4. A mineral lubricating oil composition consisting esi "f "i sentially of a major amount of mineral lubricating oil in order to demonstrate the utility and nnproved propand from about 0.01% to 5% by weight of an oil-soluble erties of this invention, the c0mpos1t1ons identified in copolymer of stearyl methacrylate, lauryl methacrylate, Table I were tested in the Chevrolet V8 Sludgmg Test, an ester of methacrylic acid and 1,5-pentanediol in the modified EX-3 test described in CRC Progress Report ratio of 1:10 to 10:1, respectively, said copolymer having No. 3, June 1, 1957, and the results were as follows: a molecular weight of from 10,000 to 500,000.
Table I P 1: il 1? Composition Active group Piston B Total 11 Total 0 Final 4 r iii g 0 i varnish varnish sludge rating plugging increase at 1. Composition A (present invention) -OO5OH 9.3 45.1 70.1 94.8 5 13 CompositionB (present invention) OC5OH 8.3 40.8 72.7 86.2 5 13 F 2. Mineral oil (X) plus 2% copolymer stearyl OOCCOH 8.3 40.0 60 77.6 13
methncrylate and monomethacrylate ester of I hexylene glycol (M.W. 143,000). C C
3. Mineral oil (X) plus 2% coploymer stearyl -O-C2OH 8.8 41.6 63.6 81.5 16 23 methacrylate and hydroxyethyl methacrylate (M.W. 230,000).
4. Mineral oil (X) plus 2% copolymer of vinyl CH2CH2 8.5 40.1 70.2 84.0 25 27 pyrrolidone and lauryl methacrylate (M.W. 500,000). CE C=O 5. Mineral oil (X) plus 2% copolymer of lauryl 8.5 39.5 61.0 77.6 79 23 methacrylate, stearyl methecrylate, 2-methyl-5- vinylpyridine (M.W. 500,000).
N/ CH3 8 10, perfect. b 50, perfect. 100, perfect. a 100, perfect.
References Cited by the Examiner UNITED STATES PATENTS 2,892,790 6/59 Stuart et a1 25256 2,892,792 6/59 Stewart et al 25256 2,892,819 6/59 Stewart et a1. 25256 X 2,913,439 11/59 Bondi et a1 25256 X 2,927,013 3/60 Lowe 44-62 2,949,445 8/60 Blake 26086.1 2,980,658 4/61 Ham 26086.1 2,994,663 8/61 Lowe et a1. 252-56 FOREIGN PATENTS 590,443 1/60 Canada.
DANIEL E. WYMAN, Primary Examiner. JULIUS GREENWALD, JOSEPH R. LIBERMAN,
Examiners.

Claims (1)

1. A MINERAL LUBRICATING OIL COMPOSITION CONSISTING ESSENTIALLY OF A MAJOR AMOUNT OF MINERAL LUBRICATING OIL AND FROM ABOUT 0.01% TO 5% BY WEIGHT OF AN OIL-SOLUBLE COPOLYMER OF A C12-20 ALKYL METHACRYLATE AND AN ESTER OF METHACRYLIC ACID AND AN ALPHA, OMEGA C5-7 ALKANEDIOL IN THE RATIO OF 1:10 TO 10:1, RESPECTIVELY, SAID COPOLYMER HAVING A MOLECULAR WEIGHT OF FROM 10,000 TO 500,000.
US71403A 1960-11-25 1960-11-25 Lubricants and polymeric additives therefor Expired - Lifetime US3198739A (en)

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GB41977/61A GB947800A (en) 1960-11-25 1961-11-23 Polymeric compounds suitable as lubricating oil additives and lubricating oils containing them
DES76807A DE1237721B (en) 1960-11-25 1961-11-23 lubricant
FR879828A FR1306897A (en) 1960-11-25 1961-11-23 Polymeric compounds suitable as lubricating oil additives, and lubricating oils containing these compounds

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EP0418610A1 (en) * 1989-09-09 1991-03-27 Röhm Gmbh Viscosity index improver, with a dispersant activity
EP0569639A1 (en) * 1992-03-20 1993-11-18 Rohm And Haas Company Dispersant polymethacrylate viscosity index improvers
EP0570093A1 (en) * 1992-03-20 1993-11-18 Rohm And Haas Company Ashless dispersant poly(meth)acrylate polymers
US5726136A (en) * 1994-10-19 1998-03-10 Agip Petroli S.P.A. Multifunctional additive for lubricating oils compatible with fluoroelastomers
US6475964B1 (en) * 1994-08-03 2002-11-05 Roehm Gmbh & Co. Kg Motor oil with high dispersivity and good wear protection characteristics
WO2009095483A2 (en) * 2008-01-30 2009-08-06 Shell Internationale Research Maatschappij B.V. Lubricating composition

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GB947800A (en) 1964-01-29

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