EP0125144B1 - Fluides fonctionnels et lubrifiants ayant une tolérance à l'eau ameliorée - Google Patents

Fluides fonctionnels et lubrifiants ayant une tolérance à l'eau ameliorée Download PDF

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Publication number
EP0125144B1
EP0125144B1 EP84303141A EP84303141A EP0125144B1 EP 0125144 B1 EP0125144 B1 EP 0125144B1 EP 84303141 A EP84303141 A EP 84303141A EP 84303141 A EP84303141 A EP 84303141A EP 0125144 B1 EP0125144 B1 EP 0125144B1
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EP
European Patent Office
Prior art keywords
alkyl
oil
carbon atoms
composition according
phosphite
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP84303141A
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German (de)
English (en)
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EP0125144A3 (en
EP0125144A2 (fr
Inventor
Lawrence Robert Brecker
Otto Ernest Loeffler
Charles Abramoff
Wiliam Kennth Cleveland
Susan Jean Wosatka
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.)
Argus Chemical Corp
ExxonMobil Technology and Engineering Co
Original Assignee
Argus Chemical Corp
Exxon Research and Engineering Co
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Publication date
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Publication of EP0125144A2 publication Critical patent/EP0125144A2/fr
Publication of EP0125144A3 publication Critical patent/EP0125144A3/en
Application granted granted Critical
Publication of EP0125144B1 publication Critical patent/EP0125144B1/fr
Expired 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • 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
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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
    • C10M2205/026—Butene
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
    • 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
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/084—Acrylate; Methacrylate
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    • 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
    • C10M2209/086—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 polycarboxylic, e.g. maleic acid
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    • C10M2215/086—Imides
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    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10M2219/089—Overbased salts
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    • 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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    • C10M2223/042—Metal salts thereof
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    • C10M2229/02—Unspecified siloxanes; Silicones
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Definitions

  • This invention relates to functional fluids and lubricants which exhibit improved water tolerance properties. More particularly, the invention relates to mineral oil or synthetic oil based functional fluid compositions which contain effective amounts of certain oil-soluble, alkoxypolyethyleneoxy mono- or diacid phosphite ester additives, which additives are highly effective in improving the water tolerance properties of such compositions.
  • U.S. Patent No. 2,280,450 describes hydrocarbon oils of improved resistance to corrosion containing a small amount of a substantially stable oil-soluble water-in-soluble reaction product of tricresyl phosphite and octyl phenoxyethanol.
  • the mole ratio of tricresyl phosphite to octyl phenoxyethanol varies from 1:1 to about 1:2.5.
  • the reaction product is described as a complex ester of phosphorous acid, which may or may not contain unreacted octyl phenoxyethanol.
  • the product is not however an acid phosphite, and it is not suggested that the water tolerance of the resulting composition is improved.
  • U.S. Patent No. 3,583,915 provides industrial fluid compositions and lubricant compositions containing improved load-carrying additives, including diorgano hydrogen phosphonate in which at least one organic group is an aliphatic group containing at least fourteen carbon atoms in admixture with an active sulfur compound.
  • U.S. Patent No. 3,652,410 provides multifunctional lubricant additive compositions and lubricating oils containing, among other things, an organic acid phosphate or organic phosphite containing at least one alkyl or alkenyl group having from about 12 to about 24 carbon atoms. Also present is a mineral oil soluble or dispersible basic detergent, a mineral oil antioxidant, a sulfurized fat, or an alkyl sulfide or alkyl polysulfide.
  • U.S. Patent No. 4,346,148 and U.S. Patent No. 4,358,509 describe reaction products of alkoxylated alkyl phenol and a phosphorus trihalide which are included in lubricating compositions useful in metal-working operations, imparting corrosion resistance, extreme pressure properties, and protection against wear of working parts.
  • U.S. Patent No. 3,115,465 provides antioxidant combinations for organic materials, including lubricants, comprising an oil-soluble phosphite ester having the formula: wherein R 1 and R 2 are alkyl, alkoxyalkyl, haloalkyl, cycloalkyl, halocycloaikyl, aralkyl, aryl, alkaryl, haloaryl, or haloalkaryl radicals and R 3 is hydrogen or one of the aforesaid radicals; and from about 0.01 to about 5, preferably 0.25 to 2%, by weight based on the oil of a methylene bis-phenol having the formula: wherein R 4 is an alkyl group containing 3 to 12 carbon atoms, the group being branched on its alpha carbon atom, and R s is an alkyl group of 1 to 12 carbon atoms.
  • United States Patent 2241244 discloses lubricants containing certain similar phosphite esters with alkyl groups
  • Water compatability is a highly significant property of functional fluids and lubricants, which, under severe conditions, come into contact with water and in the absence of acceptable water tolerance properties the fluid will have its lubricating and power transmission properties substantially reduced.
  • the specifications of many equipment manufacturers require that fluids and lubricants used therein have certain water tolerance properties, for example, fluids for use in agricultural machinery, such as tractor fluids.
  • improved function fluids and lubricating compositions comprising major amount of a synthetic or mineral oil or lubricating viscosity and an amount, effective to improve the water tolerance properties of the composition, of an oil-soluble alkoxypolyethyleneoxy acid phosphite ester additive of the formula: wherein R 1 is alkyl or alkenyl containing 9 or more carbon atoms and R 2 is OH, alkoxy, oxy-alkenyl, or R 1 O[CH 2 CH 2 O] x ; in which the total number of carbon atoms in the alkyl, alkenyl, alkoxy or oxyalkenyl groups is 9 to 36; and x is a number (which can be a whole number or a fractional number) representing the average number of [CH 2 CH 2 0] groups and ranges from 2 to 4.
  • Preferred phosphite additives are those wherein x is 2, 2.5, 3.5 or 4.
  • the alkyl and alkenyl groups include octyl, 2-ethylhexyl, isooctyl, tertiary-octyl and octenyl and in R, and R 2 they include onyl, isononyl, tertiary-nonyl, secondary nonyl, decyl, isodecyl, undecyl, doecyl, tridecyl, palmityl (i.e., hexadecyl), stearyl, (i.e., octadecyl), and isostearyl (i.e., isooctadecyl); octenyl, nonenyl, decenyl, dodecenyl, oleyl (i.e., octadecenyl), linoleyl (i.e., octadecadineyl) and
  • Acid phosphites include di(nonyl-di(ethyleneoxy)) phosphite, di(isodecyl- tri(ethyleneoxy)) phosphite, di(hexadecyl-tetra-(ethyleneoxy)) phosphite, di(octadecyl-tri(ethyleneoxy)) phosphite, octadecyl-di(ethyleneoxy)phosphite, nonyl-di(ethyleneoxy) nonyl phosphite, isodecyl- tri(ethyleneoxy) octadecatrienyl phosphite, hexadecyl-tetra(ethyleneoxy) octadecyl phosphite, octadecyl- tri(ethyleneoxy) octadecyl phosphite, and octadecyl di(ethyleneoxy) o
  • the oil-soluble phosphite ester additive of this invention will provide effective water tolerance properties to a wide variety of functional fluid and lubricating compositions and these include hydraulic fluids, compressor oils, pumps oils, tractor fluids and universal tractor fluid compositions, gear oils, hydrostatic transmission oils, power shift transmission fluids and the like.
  • Such functional fluids and lubricating compositions will also contain a number of conventional additives in amounts as required to provide their normal attendant functions.
  • Such additives include viscosity modifiers or viscosity index improvers, corrosion inhibitors, oxidation inhibitors, friction modifiers, dispersants, demulsifiers, anti-foam agent, anti-wear agents, pour point depressants, seal swellants and other special purpose additives.
  • Typical viscosity modifiers include polyisobutylene, ethylene-propylene copolymers, polymethacrylates, styrene-acrylic ester copolymers and vinyl monomer unsaturated dicarboxylic acid (or ester) copolymers.
  • Corrosion inhibitors include zinc dialkyl dithiophosphates and phosphosulfurized hydrocarbons and reaction products thereof with alkaline earth metal oxides or hydroxides, preferably in the presence of alkyl phenols and alkyl phenol thioethers. Oxidation inhibitors are illustrated by alkaline earth metal salts of alkyl (C 5 ⁇ C 12 ) phenorthioethers.
  • Dispersants are well known in the art and include oil-soluble alkenyl succinimides, e.g., the reaction products of polyisobutenyl succinic anhydrides with ethylene amines and borated derivatives.
  • Exemplary pour point depressents are C 8 ⁇ C 18 dialkylfumarate/vinyl acetate copolymers, polymethacrylates and wax- . naphthalene condensation products.
  • Anti-foam agents are typically polysiloxane materials such as silicone oil and polydimethyl siloxane; anti-wear agents include zinc dialkyl (or diaryl) dithio-phosphates and magnesium sulfonates.
  • Seal swellants are typified by mineral oils that provoke swelling, C s -C, 3 aliphatic alcohols and C 10 ⁇ C 60 hydrocarbon esters having 2-4 ester linkages such as dihexylphthalate.
  • the oil-soluble phosphite ester additive of this invention will be present in amounts effective to provide acceptable water tolerance properties to the particular composition and the desired amount will vary according to the service conditions but generally the additives of this invention will be present in an amount of about 0.05 to 5% by weight, based on the weight of the total lubricating oil or functional fluid composition and preferably from about 0.2 to 2% by weight percent.
  • Typical base oils for such functional fluids and lubricating compositions include a wide variety of hydrocarbon mineral oils such as naphthene base, paraffin base, and mixtures thereof having a lubricating viscosity range of about 34 to 45 Saybolt Universal Seconds (SUS) at 35°C.
  • Examples of synthetic oils useful in the composition of the present invention include olefin oligomers, alkylated aromatics, polybutene oils, cycloaliphatic compounds, dibasic acid esters, polyol esters, polyglycerol fluids, phosphate esters, silicone oils and halogenated hydrocarbon fluids and mixtures thereof.
  • Di(C 12 ⁇ C 15 alkyl-3EO) phosphite was prepared from triphenyl phosphite (97%), and (mixed alkyl)oxyethylene) 3 alcohols, the alkyl having from eleven to fifteen carbon atoms) using the procedure of Example I.
  • the compound has the formula:
  • Di(C 12 ⁇ C 15 alkyl-7EO) phosphite was prepared from triphenyl phosphite (97%), and mixed C 12 ⁇ C 15 (oxyethylene) 7 alcohols, using the procedure of Example I.
  • the compound has the formula:
  • Ethoxylated nonyl phenol (9.5EO) phosphite was prepared from triphenyl phosphite and ethoxylated nonylphenol using the procedure of Example I.
  • the compound has the formula:
  • Mono (C 9-11 alkyl 2.5EO) mono oleyl phosphite was prepared from triphenyl phosphite ((mixed alkyl oxyethylene) 2 . s alcohols, the alkyl having from nine to eleven carbon atoms), and oleyl alcohol using the procedure of Example I.
  • the compound has the formula:
  • Typical functional fluids or lubricating composition of the present invention will contain a number of conventional additives in typical amounts as required to provide their normal attendant functions. Such additive components and their usual ranges are set forth below.
  • the foregoing composition is referred to as Base Fluid and a tractor hydraulic fluid corresponding to the Base Fluid was evaluated for water tolerance with various additives as set forth below.
  • the mineral oil used in the Base Fluid had a kinematic viscosity of 69.8 centistokes (69.8 x 10 -2 m 2 S -1 at 37.08°C and 14.5 centistokes (14.5 x 10 -2 m 2 S -1 at 98.9°C .
  • the test used was the International Harvester Water Tolerance Test IH BI-7; January, 1980 contained in the International Harvester Engineering Materials Specification for Combination Hydraulic and Transmission Fluid.
  • the results of evaluations are tabulated below in the Table, The data include comparisons with Control A, Control B and two commercially available Surfactants A (sorbitan oleate) and B (ethoxylated fatty acid ester of sorbitol anhydride). All additives were employed in the same Base Fluid at concentration of 1 % by weight.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Claims (10)

1. Composition de fluide fonctionnel, comprenant une quantité dominante d'une huile synthétique ou minerale der viscosité propre à la lubrication et 0,05 à 5% en poids, par rapport au poids d'huile, d'une additif qui est un ester phosphitique soluble dans l'huile, répondant à la formule:
Figure imgb0021
dans laquelle R, est un groupe alkyle ou alcènyle contenant 9 ou plus de 9 atomes de carbone et R2 est un groupe OH, alkoxy, oxy-alcényle ou R1O (CH2CH20)x, où le nombre total d'atomes de carbone dans les groupes alkyle, alcényle alkoxy ou oxyalcényle est de 9 à 36 et x est un nombre représentant le nombre moyen de groupes (CH2CH20) et se situe dans l'intervalle de 2 à 4.
2. Composition suivant la revendication 1, dans laquelle x est égal 2, 2,5, 3, 3,5 ou 4.
3. Composition suivant la revendication 1 ou la revendication 2, dans lauelle R1 est un groupe alkyle ayant neuf à onze atomes de carbone.
4. Composition suivant la revendication 1 ou la revendication 2, dans lauelle R1 est un groupe alkyle ayant douze à quinze atomes de carbone.
5. Composition suivant la revendication 1, dans laquelle l'ester phosphitique répond à la formule:
Figure imgb0022
6. Composition suivant la revendication 1, dans laquelle l'ester phosphitique répond à la formule:
Figure imgb0023
et l'huile est une huile minérale hydrocarbonée.
7. Composition suivant la revendication 1, dans laquelle l'ester phosphitique répond à la formule:
Figure imgb0024
8. Composition suivant l'une quelconque des revendications 1 à 7, destinée à être utilisée comme fluide pour tracteur.
9. Composition d'huile hydrocarbonée suivant l'une quelconque des revidications 1 à 8, dans laquelle la quantité d'additif se situe dans l'intervalle de 0,2 à 2% en poids de l'huile.
10. Utilisation pour améliorer la tolérance à l'eau d'une composition de fluide fonctionnel comprenant une quantité dominante d'une huile synthétique ou minérale de viscosité propre à la lubrication et 0,05 à 5% en poids, par rapport au poids de l'huile, d'un additif qui est un ester phosphitique soluble dans l'huile de formule
Figure imgb0025
dans laquelle R1 est un groupe alkyle ou alcènyle contenant 9 ou plus de 9 atomes de carbone et R2 est un groupe OH, alkoxy, oxy-alcényle ou R10 (CH2CH20)x, où le nombre total d'atomes de carbone dans les groupes alkyle, alcényle alkoxy ou oxyalcényle est de 9 à 36 et x est un nombre représentant le nombre moyen de groupes (CH2CH20) et se situe dans l'intervalle de 2 à 4.
EP84303141A 1983-05-10 1984-05-09 Fluides fonctionnels et lubrifiants ayant une tolérance à l'eau ameliorée Expired EP0125144B1 (fr)

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US4880553A (en) * 1985-12-30 1989-11-14 The Lubrizol Corporation Methylene linked aromatic pour point depressant
US4753745A (en) * 1985-12-30 1988-06-28 The Lubrizol Corporation Methylene linked aromatic pour point depressant
US4784781A (en) * 1987-02-27 1988-11-15 The Lubrizol Corporation Lubricating oil compositions containing multi-functional additive component
US5250203A (en) * 1987-02-27 1993-10-05 The Lubrizol Corporation Lubricating oil compositions containing a polyoxyalkylene carboxylic acid salt additive
JPH05230488A (ja) * 1992-02-20 1993-09-07 Nippon Oil Co Ltd フッ化アルカン冷媒用冷凍機油組成物

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US2241244A (en) * 1939-03-25 1941-05-06 Texas Co Organic phosphite compound and method of manufacturing same
US4346148A (en) * 1979-05-04 1982-08-24 The Lubrizol Corporation Phosphorus-containing compositions, lubricants containing them and metal workpieces coated with same
JPS6043394B2 (ja) * 1983-02-07 1985-09-27 出光興産株式会社 金属加工油

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CA1238034A (fr) 1988-06-14
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AU2785984A (en) 1984-11-15
EP0125144A2 (fr) 1984-11-14
JPS59230093A (ja) 1984-12-24

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