WO2019003178A1 - Compositions d'huile lubrifiante contenant des composés détergents - Google Patents

Compositions d'huile lubrifiante contenant des composés détergents Download PDF

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Publication number
WO2019003178A1
WO2019003178A1 PCT/IB2018/054806 IB2018054806W WO2019003178A1 WO 2019003178 A1 WO2019003178 A1 WO 2019003178A1 IB 2018054806 W IB2018054806 W IB 2018054806W WO 2019003178 A1 WO2019003178 A1 WO 2019003178A1
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WIPO (PCT)
Prior art keywords
lubricating oil
detergent
alkylhydroxybenzoate
oil composition
tbn
Prior art date
Application number
PCT/IB2018/054806
Other languages
English (en)
Inventor
Alexander Bowman Boffa
Walter Alexander Hartgers
Seyedeh Mahboobeh Hosseini
Curtis Bay Campbell
Original Assignee
Chevron Oronite Company Llc
Chevron Oronite Technology B.V.
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Filing date
Publication date
Application filed by Chevron Oronite Company Llc, Chevron Oronite Technology B.V. filed Critical Chevron Oronite Company Llc
Priority to CA3068667A priority Critical patent/CA3068667C/fr
Priority to CN201880041829.2A priority patent/CN110785477A/zh
Priority to EP18749527.0A priority patent/EP3645681B1/fr
Priority to JP2019571442A priority patent/JP7348079B2/ja
Publication of WO2019003178A1 publication Critical patent/WO2019003178A1/fr

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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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/50—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring monocarboxylic
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/54—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/26—Overbased carboxylic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/26—Overbased carboxylic acid salts
    • C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
    • 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
    • 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
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10N2010/12—Groups 6 or 16
    • 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
    • C10N2020/071—Branched chain compounds
    • 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
    • C10N2030/04—Detergent property or dispersant property
    • 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
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2030/52—Base number [TBN]
    • 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
    • C10N2030/54—Fuel economy

Definitions

  • detergent additives are proportioned with other lubricating additives to provide lubricating oil compositions that exhibit certain desired lubricating properties.
  • Metal- containing detergents function both as detergents to control deposits, and as acid neutralizers or rust inhibitors, thereby reducing wear, controlling corrosion, and extending engine life.
  • the present disclosure generally relates to lubricating oil compositions which simultaneously achieve wear control and corrosion inhibition, while also achieving improved fuel economy.
  • the lubricating oil compositions are suitable for automotive engines, motorcycle engines, natural gas engines, dual fuel engines, railroad locomotive engines, mobile natural gas engines, and as functional, fluids for automotive and industrial applications.
  • the present invention is based on the surprising discovery that a lubricating oil composition containing more highly overbased metal hydroxybenzoate detergent, having a TBN of 600 mgKOH/g or greater on an actives basis, exhibits improved lubricating properties such as superior performance at low temperatures, BN retention, oxidative and thermal stability, corrosion resistance, and oxidative and thermal stability, in addition to providing a more cost effective formulating approach over the use of overbased hydroxybenzoate detergent technology previously described in the art.
  • a lubricating oil composition which comprises:
  • one or more detergents comprising at least one alkylhydroxybenzoate compound derived from isomerized NAO having from about 10 to about 40 carbon atoms, wherein the TBN of the alkylhydroxybenzoate compound is at least 600 mgKOH/gm on an actives basis.
  • a lubricating oil composition comprising:
  • TBN of the alkylhydroxybenzoate compound is at least 600 mgKOH/gm on an actives basis.
  • a "major amount” means in excess of 50 weight % of a composition.
  • a “minor amount” means less than 50 weight % of a composition, expressed in respect of the stated additive and in respect of the total mass of all the additives present in the composition, reckoned as active ingredient of the additive or additives.
  • Active ingredients or “actives” or “oil free” refers to additive material that is not diluent or solvent.
  • All percentages reported are weight % on an active ingredient basis (i.e., without regard to carrier or diluent oil) unless otherwise stated.
  • ppm means parts per million by weight, based on the total weight of the lubricating oil composition.
  • Total base number was determined in accordance with ASTM D2896.
  • Metal refers to alkali metals, alkaline earth metals, or mixtures thereof.
  • High temperature high shear (HTHS) viscosity at 150°C was determined in accordance with ASTM D4863.
  • KVioo Kinematic viscosity at 100°C
  • CCS Cold Cranking Simulator
  • Olefins refers to a class of unsaturated aliphatic hydrocarbons having one or more carbon-carbon double bonds, obtained by a number of processes. Those containing one double bond are called mono-alkenes, and those with two double bonds are called dienes, alkyldienes, or diolefins. Alpha olefins are particularly reactive because the double bond is between the first and second carbons. Examples are 1-octene and 1-octadecene, which are used as the starting point for medium-biodegradable surfactants. Linear and branched olefins are also included in the definition of olefins.
  • Normal Alpha Olefins refers to olefins which are straight chain, non-branched hydrocarbons with carbon-carbon double bond present in beginning and end of the chain.
  • Isomenzed Normal Alpha Olefin refers to an alpha olefin that has been subjected to isomerization conditions which results in an alteration of the distribution of the olefin species present and/or the introduction of branching along the alkyl chain.
  • the isomenzed olefin product may be obtained by isomerizing a linear alpha olefin containing from about 10 to about 40 carbon atoms, preferably from about 20 to about 28 carbon atoms, and preferably from about 20 to about 24 carbon atoms.
  • the present disclosure is directed to a lubricating oil composition
  • a lubricating oil composition comprising: (a) a major amount of an oil of lubricating viscosity, and
  • TBN of the alkylhydroxybenzoate compound is at least 600 mgKOH/gm on an actives basis.
  • a lubricating oil composition comprising:
  • TBN of the alkylhydroxybenzoate compound is at least 600 mgKOH/gm on an actives basis.
  • the alkylhydroxybenzoate detergent compound derived from Cio - C40 isomerized NAO has a TBN of at least 600, 600 or greater, from 600 - 800, 600 - 750, 600 - 700 mgKOH/gram on an actives basis.
  • the alkylhydroxybenzoate detergent derived from Cio - C40 isomerized NAO with a TBN of 600 mgKOH/gram or greater on an oil- free basis can be prepared as described in US Patent 8,993,499 which is herein incorporated in its entirety.
  • the alkylhydroxybenzoate detergent derived from Cio - Cw isomerized NAO is a Ca alkylhydroxybenzoate detergent.
  • the alkylhydroxybenzoate detergent derived from Cio - C40 isomerized NAO can be an alkylated hydroxybenzoate detergent.
  • the detergent can be a salicylate detergent.
  • the detergent can be a carboxylate detergent.
  • the alkylhydroxybenzoate detergent with a TBN of 600 mgKOH/gram or greater on an oil-free basis is made from an alkylphenol having an alkyl group derived from an isomerized alpha olefin having from about 14 to about 28, or from about 20 to about 24 carbon atoms per molecule.
  • the alkylhydroxybenzoate detergent derived from Cio - C40 isomerized NAO with a TBN of 600 mgKOH/gram or greater on an actives basis is made from one or more alkylphenols with an alkyl group derived from Cio - C40 isomerized NAO and one or more alkylphenols with an alkyl group different from CIO - C40 isomerized NAO.
  • the one or more alkylphenols with an alkyl group different from Cio - C40 isomerized NAO has a highly branched alkyl group of at least 9 carbon atoms, from 9 to 24, and from 10- 15 carbon atoms.
  • the lubricating oil composition comprises about 0.01 to 2 wt.% in terms of Ca content of the alkylhydroxybenzoate detergent derived from Cio - C40 isomerized NAO with a TBN of 600 mgKOH/gram or greater on an actives basis, preferably 0.1 to 1 wt. %, more preferably 0.05 to 0.5 wt. %, more preferably 0.1 to 0.5 wt%.
  • the lubricating oil composition comprises the alkylhydroxybenzoate derived from Cio - C40 isomerized NAO with TBN 600 or more on an active basis is an automotive engine oil, a gas engine oil, a motorcycle oil, a dual fuel engine oil, a mobile gas engine oil, or a locomotive engine oil.
  • the lubricating oil composition comprises the alkylhydroxybenzoate derived from Cio - C40 isomerized NAO with a TBN of 600 mgKOH/gram or more on an oil-free basis is a functional fluid for automotive and industrial applications, such as transmission oil, hydraulic oil, tractor fluid, gear oil, et.
  • the lubricating oil composition comprises the alkylhydroxybenzoate derived from Cio - C40 isomerized NAO with a TBN of 600 mgKOH/gram or more on an actives basis is a multi-grade oil.
  • the lubricating oil composition comprises the alkylhydroxybenzoate derived from Cio - C40 isomerized NAO with a TBN of 600 mgKOH/gram or more on an actives basis lubricates crankcase, gear as well as clutches. Additional Detergents
  • the lubricating oil composition of the present invention can further contain one or more overbased detergents having a TBN of 10-800, 10-700, 30-690, 100-600, 150-600, 150- 500, 200-450 mg KOH/g on an actives basis.
  • Detergents that may be used include oil-soluble overbased sulfonate, non- sulfur containing phenate, sulfurized phenates, salixarate, salicylate, saiigenin, complex detergents and naphthenate detergents and other oil-soluble alkylhydroxybenzoate s of a metal, particularly the alkali or alkaline earth metals, e.g., barium, sodium, potassium, lithium, calcium, and magnesium.
  • the most commonly used metals are calcium and magnesium, which may both be present in detergents used in a lubricant, and mixtures of calcium and/or magnesium with sodium.
  • Overbased metal detergents are generally produced by carbonating a mixture of hydrocarbons, detergent acid, for example: sulfonic acid, alkylhydroxybenzoate etc., metal oxide or hydroxides (for example calcium oxide or calcium hydroxide) and promoters such as xylene, methanol and water.
  • detergent acid for example: sulfonic acid, alkylhydroxybenzoate etc.
  • metal oxide or hydroxides for example calcium oxide or calcium hydroxide
  • promoters such as xylene, methanol and water.
  • the calcium oxide or hydroxide reacts with the gaseous carbon dioxide to form calcium carbonate.
  • the sulfonic acid is neutralized with an excess of CaO or Ca(OH)2, to form the sulfonate.
  • Overbased detergents may be low overbased, e.g., an overbased salt having a
  • the TBN of a low overbased salt may be from about 30 to about 100. In another embodiment, the TBN of a low overbased salt may be from about 30 to about 80.
  • Overbased detergents may be medium overbased, e.g., an overbased salt having a TBN from about 100 to about 250. In one embodiment, the TBN of a medium overbased salt may be from about 100 to about 200. In another embodiment, the TBN of a medium overbased salt may be from about 125 to about 175.
  • Overbased detergents may be high overbased, e.g., an overbased salt having a TBN above 250. In one
  • the TBN of a high overbased salt may be from about 250 to about 800 on an actives basis.
  • the detergent can be one or more alkali or alkaline earth metal salts of an alkyl-substituted hydroxyaromatic carboxylic acid.
  • hydroxyaromatic compounds include mononuclear monohydroxy and polyhydroxy aromatic hydrocarbons having 1 to 4, and preferably 1 to 3, hydroxyl groups. Suitable
  • hydroxyaromatic compounds include phenol, catechol, resorcinol, hydroquinone, pyrogallol, cresol, and the like.
  • the preferred hydroxyaromatic compound is phenol.
  • the alkyl substituted moiety of the alkali or alkaline earth metal salt of an alkyl-substituted hydroxyaromatic carboxylic acid is derived from an alpha olefin having from about 10 to about 80 carbon atoms.
  • the olefins employed may be linear, isomerized linear, branched or partially branched linear.
  • the olefin may be a mixture of linear olefins, a mixture of isomerized linear olefins, a mixture of branched olefins, a mixture of partially branched linear or a mixture of any of the foregoing.
  • the mixture of linear olefins that may be used is a mixture of normal alpha olefins selected from olefins having from about 10 to about 40 carbon atoms per molecule.
  • the normal alpha olefins are isomerized using at least one of a solid or liquid catalyst.
  • At least about 50 mole%, at least about 75 mole%, at least about 80 mole%, at least about 85 mole%, at least about 90 mole%, at least about 95 mole% of the alkyl groups contained within the alkali or alkaline earth metal salt of an alkyl- substituted hydroxyaromatic carboxylic acid such as the alkyl groups of an alkaline earth metal salt of an alkyl-substituted hydroxybenzoic acid detergent are a C20 or higher.
  • the alkali or alkaline earth metal salt of an alkyl-substituted hydroxyaromatic carboxylic acid is an alkali or alkaline earth metal salt of an alkyl- substituted hydroxybenzoic acid that is derived from an alkyl-substituted hydroxybenzoic acid in which the alkyl groups are C20 to about C28 normal alpha-olefins.
  • the alkyl group is derived from at least two alkylated phenols.
  • the alkyl group on at least one of the at least two alkyl phenols is derived from an isornerized alpha olefin.
  • the alkyl group on the second alkyl phenol may be derived from branched or partially branched olefins, highly somerized olefins or mixtures thereof.
  • the alkali or alkaline earth metal salt of an alkyl- substituted hydroxyaromatic carboxylic acid is a salicylate derived from an alkyl group with 20-40 carbon atoms, preferably 20-28 carbon atoms, more preferably, isomerized 20-24 NAO.
  • Sulfonates may be prepared from sulfonic acids which are typically obtained by the sulfonation of alkyl substituted aromatic hydrocarbons such as those obtained from the fractionation of petroleum or by the alkylation of aromatic hydrocarbons. Examples included those obtained by alkylating benzene, toluene, xylene, naphthalene, diphenyl or their halogen derivatives.
  • the alkylation may be carried out in the presence of a catalyst with alkylating agents having from about 3 to more than 70 carbon atoms.
  • the alkaryl sulfonates usually contain from about 9 to about 80 or more carbon atoms, preferably from about 16 to about 60 carbon atoms, preferably about 16 to 30 carbon atoms, and more preferably 20-24 carbon atoms per alkyl substituted aromatic moiety.
  • Metal salts of phenols and sulfurized phenols which are sulfurized phenate detergents, are prepared by reaction with an appropriate metal compound such as an oxide or hydroxide and neutral or overbased products may be obtained by methods well known in the art.
  • Sulfurized phenols may be prepared by reacting a phenol with sulfur or a sulfur containing compound such as hydrogen sulfide, sulfur monohalide or sulfur dihalide, to form products which are generally mixtures of compounds in which 2 or more phenols are bridged by sulfur containing bridges.
  • the sulfur can be employed either as molten sulfur or as a solid (e.g., powder or particulate) or as a solid suspension in a compatible hydrocarbon liquid.
  • calcium hydroxide As the calcium base because of its handling convenience versus, for example, calcium oxide, and also because it affords excellent results.
  • Other calcium bases can also be used, for example, calcium alkoxides.
  • Suitable alkylphenols which can be used are those wherein the alkyl substituents contain a sufficient number of carbon atoms to render the resulting overbased sulfurized calcium alkylphenate composition oil-soluble. Oil solubility may be provided by a single long chain alkyl substitute or by a combination of alkyl substituents. Typically, the alkylphenol used will be a mixture of different alkylphenols, e.g., C20 to C24 alkylphenol.
  • suitable alkyl phenolic compounds will be derived from isomerized alpha olefin alkyl groups having from about 10 to about 40 carbon atoms per molecule, having an isomerized level (1) of the alpha olefin between from about 0.1 to about 0.4.
  • suitable alkyl phenolic compounds will be derived from alkyl groups which are branched olefinic propylene oligomers or mixture thereof having from about 9 to about 80 carbon atoms.
  • the branched olefinic propylene oligomer or mixtures thereof have from about 9 to about 40 carbon atoms.
  • the branched olefinic propylene oligomer or mixtures thereof have from about 9 to about 18 carbon atoms. In one embodiment, the branched olefinic propylene oligomer or mixtures thereof have from about 9 to about 12 carbon atoms.
  • suitable alkyl phenolic compounds comprise distilled cashew nut shell liquid (CNSL) or hydrogenated distilled cashew nut shell liquid.
  • Distilled CNSL is a mixture of biodegradable meta-hydrocarbyl substituted phenols, where the hydrocarbyl group is linear and unsaturated, including cardanol. Catalytic liydrogenation of distilled CNSL gives rise to a mixture of meta-hydrocarbyl substituted phenols
  • the alkylphenols can be para-alkylphenols, meta-alkylphenols or ortho alkylphenols. Since it is believed that p-alkylphenols facilitate the preparation of highly overbased calcium sulfurized alkylphenate where overbased products are desired, the alkylphenol is preferably predominantly a para alkylphenol with no more than about 45 mole percent of the alkylphenol being ortho alkylphenols; and more preferably no more than about 35 mole percent of the alkylphenol is ortho alkylphenol.
  • Alkyl-hydroxy toluenes or xylenes, and other alkyl phenols having one or more alkyl substituents in addition to at least one long chained alkyl substituent can also be used.
  • the catalytic hydrogenation of distilled CNSL gives rise to a mixture of meta-hydrocarbyl substituted phenols.
  • the one or more overbased detergent can be a complex or hybrid detergent which is known in the art as compr sing a surfactant system derived from at least two surfactants described above.
  • the one or more overbased detergent can be a salicylate with an alkyl group having 20-28 carbon atoms, more preferably 20-24Ccarbon atoms.
  • the one or more overbased detergent can be a salicylate with an alkyl group derived from Ci4-isNAO and contribute less than 0.05 wt%, preferably less than 0.025 wt%, more preferably less than 0.01 wt% in terms of Ca content to the lubricating oil.
  • the amount of the detergent can be from about 0.001 wt. % to about
  • the lubricating oil composition disclosed herein can comprise one or more antiwear agent.
  • Antiwear agents reduce wear of metal parts.
  • Suitable anti-wear agents include dihydrocarbyl dithiophosphate metal salts such as zinc dihydrocarbyl dithiophosphates
  • R 1 and R 2 may be the same of different hydrocarbyl radicals having from 1 to
  • R 18 carbon atoms and including radicals such as alkyl, alkenyl, aryl, arylalkyl, alkaryl and cycloaliphatic radicals.
  • Particularly preferred as R 1 and R 2 groups are alkyl groups having from 2 to 8 carbon atoms (e.g., the alkyl radicals may be ethyl, ⁇ -propyl, isopropyl, n- butyl, isobutyl, sec-butyl, «-pentyl, isopentyl, «-hexyl, isohexyl, 2-ethylhexyl).
  • the zinc dihydrocarbyl dithiophosphate can therefore comprise zinc dialkyl dithiophosphates.
  • the zinc dialkyl dithiophosphate is a primary, secondary zinc dialkyl dithiophosphate, or a combination thereof.ZDDP may be present at 3 wt. % or less (e.g., 0.1 to 1.5 wt. %, or 0.5 to 1.0 wt %) of the lubricating oil composition.
  • the lubricating oil composition containing the magnesium salicylate detergent described herein further comprises an antioxidant compound.
  • the antioxidant is a diphenylamine antioxidant.
  • the antioxidant is a hindered phenol antioxidant.
  • the antioxidant is a combination of a diphenylamine antioxidant and a hindered phenol antioxidant.
  • the lubricating oil composition disclosed herein can comprise one or more antioxidant.
  • Antioxidants reduce the tendency of mineral oils during to deteriorate during service. Oxidative deterioration can be evidenced by sludge in the lubricant, varnish-like deposits on the metal surfaces, and by viscosity growth.
  • Suitable antioxidants include hindered phenols, aromatic amines, and sulfurized alkylphenols and alkali and alkaline earth metals salts thereof.
  • the hindered phenol antioxidant often contains a secondary butyl and/or a tertiary butyl group as a sterically hindering group.
  • the phenol group may be further substituted with a hydrocarbyl group (typically linear or branched alkyl) and/or a bridging group linking to a second aromatic group.
  • Suitable hindered phenol antioxidants include 2,6-di- fert-butylphenol; 4-methyl-2,6-di-fert-butylphenol; 4-ethyl-2,6-di-fert-butylphenol; 4-propyl- 2,6-di-fert-butylphenol; 4-butyl-2,6-di-fert-butylphenol; and 4-dodecyl-2,6-di-fert- butylphenol.
  • antioxidants include 2,6-di-alkyl-phenolic propionic ester derivatives such as IRGANOX ® L-135 from Ciba and bis-phenolic antioxidants such as 4,4'-bis(2,6-di-fert-butylphenol) and 4,4'-methylenebis(2,6-di-fert-butylphenol).
  • Typical aromatic amine antioxidants have at least two aromatic groups attached directly to one amine nitrogen.
  • Typical aromatic amine antioxidants have alkyl substituent groups of at least 6 carbon atoms.
  • Particular examples of aromatic amine antioxidants useful herein include 4,4'- dioctyldiphenylamine, 4,4'-dinonyldiphenylamine, N-phenyl-l-naphthylamine, N-(4-tert- octyphenyl)-l-naphthylamine, and N-(4-octylphenyl)-l-naphthylamine .
  • Antioxidants may be present at 0.01 to 5 wt. % (e.g., 0.1 to 2 wt. %) of the lubricating oil composition.
  • the lubricating oil composition disclosed herein can comprise one or more dispersant.
  • Dispersants maintain in suspension materials resulting from oxidation during engine operation that are insoluble in oil, thus preventing sludge flocculation and precipitation or deposition on metal parts.
  • Dispersants useful herein include nitrogen-containing, ashless (metal-free) dispersants known to effective to reduce formation of deposits upon use in gasoline and diesel engines.
  • Suitable dispersants include hydrocarbyl succinimides, hydrocarbyl succinamides, mixed ester/amides of hydrocarbyl-substituted succinic acid, hydroxyesters of hydrocarbyl-substituted succinic acid, and Mannich condensation products of hydrocarbyl- substituted phenols, formaldehyde and polyamines. Also suitable are condensation products of polyamines and hydrocarbyl-substituted phenyl acids. Mixtures of these dispersants can also be used.
  • Baseic nitrogen-containing ashless dispersants are well-known lubricating oil additives and methods for their preparation are extensively described in the patent literature.
  • Preferred dispersants are the alkenyl succinimides and succinamides where the alkenyl-substituent is a long -chain of preferably greater than 40 carbon atoms. These materials are readily made by reacting a hydrocarbyl-substituted dicarboxylic acid material with a molecule containing amine functionality. Examples of suitable amines are polyamines such as polyalkylene polyamines, hydroxy-substituted polyamines and polyoxyalkylene polyamines.
  • Particularly preferred ashless dispersants are the polyisobutenyl succinimides formed from polyisobutenyl succinic anhydride and a polyalkylene polyamine such as a polyethylene polyamine of formula 2:
  • the polyisobutenyl group is derived from polyisobutene and preferably has a number average molecular weight (M») in a range of 700 to 3000 Daltons (e.g., 900 to 2500 Daltons).
  • the polyisobutenyl succinimide may be a bis-succinimide derived from a polyisobutenyl group having a M « of 900 to 2500 Daltons.
  • the dispersants may be post-treated (e.g., with a boronating agent or a cyclic carbonate, ethylene carbonate etc).
  • Nitrogen-containing ashless (metal-free) dispersants are basic, and contribute to the TBN of a lubricating oil composition to which they are added, without introducing additional sulfated ash. Dispersants may be present at 0.1 to 10 wt. % (e.g., 2 to 5 wt. %) of the lubricating oil composition.
  • Foam Inhibitors are basic, and contribute to the TBN of a lubricating oil composition to which they are added, without introducing additional sulfated ash.
  • Dispersants may be present at 0.1 to 10 wt. % (e.g., 2 to 5 wt. %) of the lubricating oil composition.
  • the lubricating oil composition disclosed herein can comprise one or more foam inhibitor that can break up foams in oils.
  • suitable foam inhibitors or anti-foam inhibitors include silicone oils or polydimethylsiloxanes, fluorosilicones, alkoxylated aliphatic acids, polyethers (e.g., polyethylene glycols), branched polyvinyl ethers, alkyl acrylate polymers, alkyl methacrylate polymers, polyalkoxyamines and combinations thereof.
  • the lubricating oil compositions of the present disclosure may also contain other conventional additives that can impart or improve any desirable property of the lubricating oil composition in which these additives are dispersed or dissolved.
  • Any additive known to a person of ordinary skill in the art may be used in the lubricating oil compositions disclosed herein.
  • Some suitable additives have been described in Mortier et al, “Chemistry and Technology of Lubricants", 2nd Edition, London, Springer, (1996); and Leslie R. Rudnick, "Lubricant Additives: Chemistry and Applications", New York, Marcel Dekker (2003), both of which are incorporated herein by reference.
  • the lubricating oil compositions can be blended with antioxidants, anti-wear agents, detergents such as metal detergents, rust inhibitors, dehazing agents, demulsifying agents, metal deactivating agents, friction modifiers, pour point depressants, antifoaming agents, co-solvents, corrosion-inhibitors, ashless dispersants, multifunctional agents, dyes, extreme pressure agents and the like and mixtures thereof.
  • detergents such as metal detergents, rust inhibitors, dehazing agents, demulsifying agents, metal deactivating agents, friction modifiers, pour point depressants, antifoaming agents, co-solvents, corrosion-inhibitors, ashless dispersants, multifunctional agents, dyes, extreme pressure agents and the like and mixtures thereof.
  • detergents such as metal detergents, rust inhibitors, dehazing agents, demulsifying agents, metal deactivating agents, friction modifiers, pour point depressants, antifoaming agents, co-solvents, corrosion-inhibitors, ashless
  • additives in the form of 10 to 100 wt. % active ingredient concentrates in hydrocarbon oil, e.g. mineral lubricating oil, or other suitable solvent.
  • these concentrates may be diluted with 3 to 100, e.g., 5 to 40, parts by weight of lubricating oil per part by weight of the additive package in forming finished lubricants, e.g. crankcase motor oils.
  • the purpose of concentrates is to make the handling of the various materials less difficult and awkward as well as to facilitate solution or dispersion in the final blend.
  • Each of the foregoing additives when used, is used at a functionally effective amount to impart the desired properties to the lubricant.
  • a functionally effective amount of this friction modifier would be an amount sufficient to impart the desired friction modifying characteristics to the lubricant.
  • the concentration of each of the additives in the lubricating oil composition when used, may range from about 0.001 wt. % to about 20 wt. %, from about 0.01 wt. % to about 15 wt. %, or from about 0.1 wt. % to about 10 wt. %, from about 0.005 wt.% to about 5 wt.%, or from about 0.1 wt.% to about 2.5 wt.%, based on the total weight of the lubricating oil composition.
  • the total amount of the additives in the lubricating oil composition may range from about 0.001 wt.% to about 20 wt.%, from about 0.01 wt.% to about 10 wt.%, or from about 0.1 wt.% to about 5 wt.%, based on the total weight of the lubricating oil composition.
  • Oil of lubricating viscosity Oil of lubricating viscosity
  • the oil of lubricating viscosity (sometimes referred to as “base stock” or “base oil”) is the primary liquid constituent of a lubricant, into which additives and possibly other oils are blended, for example to produce a final lubricant (or lubricant composition).
  • a base oil is useful for making concentrates as well as for making lubricating oil compositions therefrom, and may be selected from natural and synthetic lubricating oils and combinations thereof.
  • Natural oils include animal and vegetable oils, liquid petroleum oils and hydrorefined, solvent-treated mineral lubricating oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale are also useful base oils.
  • Synthetic lubricating oils include hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(l-hexenes), poly(l-octenes), poly(l-decenes); alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2- ethylhexyl)benzenes; polyphenols (e.g., biphenyls, terphenyls, alkylated polyphenols); and alkylated diphenyl ethers and alkylated diphenyl sulfides and the derivatives, analogues and homologues thereof.
  • hydrocarbon oils such as polymerized and interpolymerized olefins (e.g
  • Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids (e.g., malonic acid, alkyl malonic acids, alkenyl malonic acids, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, fumaric acid, azelaic acid, suberic acid, sebacic acid, adipic acid, linoleic acid dimer, phthalic acid) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol).
  • dicarboxylic acids e.g., malonic acid, alkyl malonic acids, alkenyl malonic acids, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, fumaric acid, azelaic acid, suberic acid, sebac
  • esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di- «-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
  • Esters useful as synthetic oils also include those made from C5 to C12 monocarboxylic acids and polyols, and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol.
  • the base oil may be derived from Fischer-Tropsch synthesized hydrocarbons.
  • Fischer-Tropsch synthesized hydrocarbons are made from synthesis gas containing H2 and CO using a Fischer-Tropsch catalyst. Such hydrocarbons typically require further processing in order to be useful as the base oil.
  • the hydrocarbons may be hydroisomerized; hydrocracked and hydroisomerized; dewaxed; or hydroisomerized and dewaxed; using processes known to those skilled in the art.
  • Unrefined, refined and re-refined oils can be used in the present lubricating oil composition.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from retorting operations a petroleum oil obtained directly from distillation or ester oil obtained directly from an esterification process and used without further treatment would be unrefined oil.
  • Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques, such as distillation, solvent extraction, acid or base extraction, filtration and percolation are known to those skilled in the art.
  • Re-refined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in service. Such re-refined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques for approval of spent additive and oil breakdown products.
  • the base oil which may be used to make the present lubricating oil composition may be selected from any of the base oils in Groups I-V as specified in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines (API Publication).
  • Groups I-III are mineral oil base stocks.
  • Base oils suitable for use herein are any of the variety corresponding to API
  • the oil of lubricating viscosity for use in the lubricating oil compositions of this disclosure is typically present in a major amount, e.g., an amount of greater than 50 wt. %, preferably greater than about 70 wt. %, more preferably from about 80 to about 99.5 wt. % and most preferably from about 85 to about 98 wt. %, based on the total weight of the composition.
  • base oil as used herein shall be understood to mean a base stock or blend of base stocks which is a lubricant component that is produced by a single manufacturer to the same specifications (independent of feed source or manufacturer's location); that meets the same manufacturer's specification; and that is identified by a unique formula, product identification number, or both.
  • the base oil for use herein can be any presently known or later-discovered oil of lubricating viscosity used in formulating lubricating oil compositions for any and all such applications, e.g., engine oils, marine cylinder oils, functional fluids such as hydraulic oils, gear oils, transmission fluids, etc.
  • the base oils for use herein can optionally contain viscosity index improvers, e.g., polymeric alkylmethacrylates; olefinic copolymers, e.g., an ethylene-propylene copolymer or a styrene- butadiene copolymer; and the like and mixtures thereof.
  • viscosity index improvers e.g., polymeric alkylmethacrylates
  • olefinic copolymers e.g., an ethylene-propylene copolymer or a styrene- butadiene copolymer; and the like and mixtures thereof.
  • the viscosity of the base oil is dependent upon the application. Accordingly, the viscosity of a base oil for use herein will ordinarily range from about 2 to about 2000 centistokes (cSt) at 100° Centigrade (C).
  • the base oils used as engine oils will have a kinematic viscosity range at 100° C. of about 2 cSt to about 30 cSt, preferably about 3 cSt to about 16 cSt, and most preferably about 4 cSt to about 12 cSt and will be selected or blended depending on the desired end use and the additives in the finished oil to give the desired grade of engine oil, e.g., a lubricating oil composition having an SAE Viscosity Grade of 0W, 0W-8, OW-12, OW-16, 0W- 20, OW-26, 0W-30, OW-40, 0W-50, OW-60, 5W, 5W-20, 5W-30, 5W-40, 5W-50, 5W-60, 10W, 10W-20, 10W-30, 10W-40, 10W-50, 15W, 15W-20, 15W-30, 15W-40, 30, 40 and the like.
  • the level of sulfur in the lubricating oil compositions of the present invention is less than or equal to about 0.7 wt. %, based on the total weight of the lubricating oil composition, e.g., a level of sulfur of about 0.01 wt. % to about 0.70 wt. %, 0.01 to 0.6 wt.%, 0.01 to 0.5 wt.%, 0.01 to 0.4 wt.%, 0.01 to 0.3 wt.%, 0.01 to 0.2 wt.%, 0.01 wt. % to 0.10 wt. %.
  • the level of sulfur in the lubricating oil compositions of the present invention is less than or equal to about 0.60 wt. %, less than or equal to about 0.50 wt. %, less than or equal to about 0.40 wt. %, less than or equal to about 0.30 wt. %, less than or equal to about 0.20 wt. %, less than or equal to about 0.10 wt. % based on the total weight of the lubricating oil composition.
  • the levels of phosphorus in the lubricating oil compositions of the present invention is less than or equal to about 0.12 wt. %, based on the total weight of the lubricating oil composition, e.g., a level of phosphorus of about 0.01 wt. % to about 0.12 wt. %. In one embodiment, the levels of phosphorus in the lubricating oil compositions of the present invention is less than or equal to about 0.11 wt. %, based on the total weight of the lubricating oil composition, e.g., a level of phosphorus of about 0.01 wt. % to about 0.11 wt.
  • the levels of phosphorus in the lubricating oil compositions of the present invention is less than or equal to about 0.10 wt. %, based on the total weight of the lubricating oil composition, e.g., a level of phosphorus of about 0.01 wt. % to about 0.10 wt.
  • the levels of phosphorus in the lubricating oil compositions of the present invention is less than or equal to about 0.09 wt. %, based on the total weight of the lubricating oil composition, e.g., a level of phosphorus of about 0.01 wt. % to about 0.09 wt.
  • the levels of phosphorus in the lubricating oil compositions of the present invention is less than or equal to about 0.08 wt. %, based on the total weight of the lubricating oil composition, e.g., a level of phosphorus of about 0.01 wt. % to about 0.08 wt. %. In one embodiment, the levels of phosphorus in the lubricating oil compositions of the present invention is less than or equal to about 0.07 wt. %, based on the total weight of the lubricating oil composition, e.g., a level of phosphorus of about 0.01 wt. % to about 0.07 wt. %.
  • the levels of phosphorus in the lubricating oil compositions of the present invention is less than or equal to about 0.05 wt. %, based on the total weight of the lubricating oil composition, e.g., a level of phosphorus of about 0.01 wt. % to about 0.05 wt.
  • the level of sulfated ash produced by the lubricating oil compositions of the present invention is less than or equal to about 1.60 wt. % as determined by ASTM D 874, e.g., a level of sulfated ash of from about 0.10 to about 1.60 wt. % as determined by ASTM D 874. In one embodiment, the level of sulfated ash produced by the lubricating oil compositions of the present invention is less than or equal to about 1.00 wt. % as determined by ASTM D 874, e.g., a level of sulfated ash of from about 0.10 to about 1.00 wt. % as determined by ASTM D 874.
  • the level of sulfated ash produced by the lubricating oil compositions of the present invention is less than or equal to about 0.80 wt. % as determined by ASTM D 874, e.g., a level of sulfated ash of from about 0.10 to about 0.80 wt. % as determined by ASTM D 874. In one embodiment, the level of sulfated ash produced by the lubricating oil compositions of the present invention is less than or equal to about 0.60 wt. % as determined by ASTM D 874, e.g., a level of sulfated ash of from about 0.10 to about 0.60 wt. % as determined by ASTM D 874.
  • the isomerization level (I) of the olefin was determined by hydrogen- 1 (1H)
  • the isomerization level (I) represents the relative amount of methyl groups (-
  • n NMR integral for methylene groups with chemical shifts between 1.01 ⁇ 0.03 to 1.38 ⁇ 0.10 ppm.
  • the isomerized level (I) of the alpha olefin is between from about 0.1 to about
  • the isomerization level of the NAO is about 0.16, and having from about 20 to about 24 carbon atoms.
  • the isomerization level of the NAO is about 0.26, and having from about 20 to about 24 carbon atoms.
  • a 5W-40 lubricating oil composition was prepared that contained a major amount of a base oil of lubricating viscosity and the following additives:
  • An alkylated phenol and a Ca alkylhydroxybenzoate were prepared in substantially the same manner as in U.S. Patent No. 8,993,499 using a C20-24 isomerized normal alpha olefin.
  • the isomerization level of the alpha olefin is about 0.16.
  • the resulting alkylhydroxybenzoate composition has a TBN of about 630 and Ca content of about 22.4 wt.% on an oil-free basis.
  • An alkylated phenol and Ca alkylhydroxybenzoate were prepared in substantially the same manner as in U.S. Patent No. 8,993,499 using a C20-24 isomerized normal alpha olefin.
  • the isomerization level of the alpha olefin is about 0.16.
  • the resulting alkylhydroxybenzoate composition has a TBN of about 225 and Ca content of about 8 wt.% on an oil -free basis.
  • An alkylhydroxybenzoate was prepared from an alkylphenol with an alkyl group derived from C14-18 NAO and a TBN about 300 and Ca content about 10.6 wt. % on an oil -free basis.
  • alkylated phenol and alkylhydroxybenzoate were prepared in substantially the same manner as in U.S. Patent No. 8,030,258 using a C20-28 NAO available from CP Chem.
  • the resulting alkylhydroxybenzoate composition has a TBN of about 520 and Ca content of about 18.7 wt.% on an oil-free basis.
  • the ASTM D6594 HTCBT test is used to test diesel engine lubricants to determine their tendency to corrode various metals, specifically alloys of lead and copper commonly used in cam followers and bearings.
  • Four metal specimens of copper, lead, tin and phosphor bronze are immersed in a measured amount of engine oil.
  • the oil, at an elevated temperature (170 °C), is blown with air (5 1/h) for a period of time (168 h).
  • the copper specimen and the stressed oil are examined to detect corrosion and corrosion products, respectively.
  • the concentrations of copper, lead, and tin in the new oil and stressed oil and the respective changes in metal concentrations are reported. To be a pass the concentration of lead should not exceed 120 ppm and the copper 20 ppm.
  • a heavy duty automotive lubricating oil composition was prepared that contained a major amount of a base oil of lubricating viscosity and the following additives, to provide an SAE 15W-40 finished oil:
  • a 25 g sample was weighted into a special glass oxidator cell.
  • a catalyst was added, followed by inserting a glass stirrer.
  • the cell was then sealed and placed in an oil bath maintained at 340 °F and connected to the oxygen supply.
  • One liter of oxygen was fed into the cell while the stirrer agitated the oil sample.
  • the test was run until 1 liter of oxygen was consumed by the sample and the total time, in hours, of the sample run was reported. Higher hours to 1 Liter means better oxidation performance. Results are given in Table 4 below.
  • An alkylated phenol and a Ca alkylhydroxybenzoate were prepared in substantially the same manner as in U.S. Patent No. 8,993,499 using a C20-24 isomerized normal alpha olefin.
  • the isomerization level of the alpha olefin is about 0.16.
  • the resulting alkylhydroxybenzoate composition has a TBN of about 120 and Ca content of about 4.2 wt.% on an oil -free basis.
  • a passenger car automotive lubricating oil composition was prepared that contained a major amount of a base oil of lubricating viscosity and the following additives, to provide an SAE 5W-30 finished oil:
  • Example 6 alkylhydroxybenzoate of Example A (32.3 mMol) and Example C (23.3 mMol) in a total amount of 0.2230 wt.%.
  • Example 6
  • alkylhydroxybenzoate derived from a C20-28 NAO with a TBN of 135 on an oil free basis (24.1 mMol) and Comparative Example B (31.6 mMol) in a total amount of 0.2230 wt.%.
  • alkylhydroxybenzoate derived from a C20-28 NAO with a TBN of 135 on an oil free basis (27.7 mMol) and an HOB sulfonate (29.6 mMol) derived from a C20-24 NAO in a total amount of 0.2300 wt.%.
  • a passenger car automotive lubricating oil composition was prepared that contained a major amount of a base oil of lubricating viscosity and the following additives, to provide an SAE 5W-40 finished oil:
  • test oil is first heated, and then cooled to test temperature, in this case -40° C, in a mini-rotary viscometer cell.
  • test temperature in this case -40° C
  • Each cell contains a calibrated rotor-stator set, in which the rotor is rotated by means of a string wound around the rotor shaft and attached to a weight.
  • a series of increasing weights are applied to the string starting with a 10 g weight until rotation occurs to determine the yield stress. Results are reported as Yield Stress as the applied force in Pascals.
  • a 150 g weight is then applied to determine the apparent viscosity of the oil. The larger the apparent viscosity, the more likely it is that the oil will not be continuously and adequately supplied to the oil pump inlet. Results are reported as Viscosity in centipoise.
  • lubricating oils formulated with an alkylhydroxybenzoate detergent of the invention perform as well as or better than formulations containing alkyhydroxybenzoates which are not derived from isomerized NAO having from about 10 to about 40 carbon atoms.

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Abstract

La présente invention concerne de manière générale une composition d'huile lubrifiante comprenant : une quantité majeure d'une huile de viscosité lubrifiante, ainsi qu'un ou plusieurs détergents, au moins un détergent étant un composé d'alkylhydroxybenzoate.
PCT/IB2018/054806 2017-06-30 2018-06-28 Compositions d'huile lubrifiante contenant des composés détergents WO2019003178A1 (fr)

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JP2019571442A JP7348079B2 (ja) 2017-06-30 2018-06-28 清浄剤化合物を含有する潤滑油組成物

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021005457A1 (fr) * 2019-07-05 2021-01-14 Chevron Japan Ltd. Composition d'huile lubrifiante

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020003071A1 (fr) * 2018-06-27 2020-01-02 Chevron Oronite Technology B.V. Composition d'huile lubrifiante
JP2022547073A (ja) * 2019-09-05 2022-11-10 シェブロン・オロナイト・カンパニー・エルエルシー 潤滑油組成物
CN113249157B (zh) * 2020-02-13 2023-03-10 中国石油化工股份有限公司 黏度指数改进剂及其制备方法、用途
JP2023520938A (ja) * 2020-04-10 2023-05-22 シェブロン・オロナイト・カンパニー・エルエルシー バイオベース基油を含む潤滑油組成物
EP4185677A1 (fr) * 2020-07-21 2023-05-31 Chevron Japan Ltd. Composition d'huile lubrifiante contenant du salicylate pour véhicules hybrides
WO2024030899A1 (fr) * 2022-08-01 2024-02-08 Chevron Oronite Company Llc Composition d'huile lubrifiante pour lutter contre la corrosion

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2680096A (en) 1951-02-12 1954-06-01 California Research Corp Process for preparing sulfurized polyvalent metal phenates
US3178368A (en) 1962-05-15 1965-04-13 California Research Corp Process for basic sulfurized metal phenates
US3801507A (en) 1972-08-18 1974-04-02 Chevron Res Sulfurized metal phenates
US20090170737A1 (en) * 2007-12-28 2009-07-02 Chevron Oronite LLC Low temperature performance lubricating oil detergents and method of making the same
US20110003726A1 (en) * 2009-07-01 2011-01-06 Chevron Oronite Company Llc Low temperature performance lubricating oil detergents and method of making the same
US8030258B2 (en) 2005-07-29 2011-10-04 Chevron Oronite Company Llc Overbased alkaline earth metal alkylhydroxybenzoates having low crude sediment
US8580717B2 (en) 2009-11-24 2013-11-12 Chevron Oronite Company Llc Process for making an overbased, sulfurized salt of an alkylated hydroxyaromatic compound

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8709988B2 (en) * 2004-11-30 2014-04-29 Infineum International Limited Lubricating oil compositions
US20100029525A1 (en) * 2008-07-31 2010-02-04 Chevron Oronite Company Llc Antiwear hydraulic fluid composition with useful emulsifying and rust prevention properties
US9206374B2 (en) * 2011-12-16 2015-12-08 Chevron Oronite Sas Trunk piston engine lubricating oil compositions
SG11201405647XA (en) * 2012-03-26 2014-10-30 Lubrizol Corp Manual transmission lubricants with improved synchromesh performance
CN105814180B (zh) * 2013-11-06 2019-12-10 雪佛龙奥伦耐技术有限责任公司 船用柴油机汽缸润滑剂油组合物
JP6509239B2 (ja) * 2013-11-06 2019-05-08 シェブロン・オロナイト・テクノロジー・ビー．ブイ． 船舶用ディーゼルシリンダー潤滑油組成物
WO2016071519A1 (fr) * 2014-11-06 2016-05-12 Chevron Oronite Technology B.V. Compositions d'huiles lubrifiantes pour cylindres de moteurs diesel marins
CN104531269B (zh) * 2014-12-05 2017-06-13 中国石油天然气股份有限公司 一种船用柱塞式发动机润滑油组合物
US11168280B2 (en) * 2015-10-05 2021-11-09 Infineum International Limited Additive concentrates for the formulation of lubricating oil compositions
JP6235549B2 (ja) * 2015-12-07 2017-11-22 Ｅｍｇルブリカンツ合同会社 潤滑油組成物
JP6334503B2 (ja) * 2015-12-07 2018-05-30 出光興産株式会社 潤滑油組成物及びその製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2680096A (en) 1951-02-12 1954-06-01 California Research Corp Process for preparing sulfurized polyvalent metal phenates
US3178368A (en) 1962-05-15 1965-04-13 California Research Corp Process for basic sulfurized metal phenates
US3801507A (en) 1972-08-18 1974-04-02 Chevron Res Sulfurized metal phenates
US8030258B2 (en) 2005-07-29 2011-10-04 Chevron Oronite Company Llc Overbased alkaline earth metal alkylhydroxybenzoates having low crude sediment
US20090170737A1 (en) * 2007-12-28 2009-07-02 Chevron Oronite LLC Low temperature performance lubricating oil detergents and method of making the same
US8993499B2 (en) 2007-12-28 2015-03-31 Chevron Oronite Company Llc Low temperature performance lubricating oil detergents and method of making the same
US20110003726A1 (en) * 2009-07-01 2011-01-06 Chevron Oronite Company Llc Low temperature performance lubricating oil detergents and method of making the same
US8580717B2 (en) 2009-11-24 2013-11-12 Chevron Oronite Company Llc Process for making an overbased, sulfurized salt of an alkylated hydroxyaromatic compound

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021005457A1 (fr) * 2019-07-05 2021-01-14 Chevron Japan Ltd. Composition d'huile lubrifiante

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US20190002791A1 (en) 2019-01-03
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