US3928219A - Lubricating oil compositions of improved rust inhibition - Google Patents

Lubricating oil compositions of improved rust inhibition Download PDF

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Publication number
US3928219A
US3928219A US391469A US39146973A US3928219A US 3928219 A US3928219 A US 3928219A US 391469 A US391469 A US 391469A US 39146973 A US39146973 A US 39146973A US 3928219 A US3928219 A US 3928219A
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Prior art keywords
oil
tetronic
poly
additives
lubricating
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US391469A
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English (en)
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Andrew G Papay
Brian W Matthews
Arthur S Thomas
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Edwin Cooper Inc
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Edwin Cooper Inc
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Priority to US391469A priority Critical patent/US3928219A/en
Priority to GB36609/74A priority patent/GB1483513A/en
Priority to FR7428678A priority patent/FR2248316B1/fr
Priority to BE147863A priority patent/BE819142A/xx
Priority to DE2440531A priority patent/DE2440531A1/de
Priority to NL7411260.A priority patent/NL162131C/xx
Priority to IT26572/74A priority patent/IT1020169B/it
Priority to CA207,716A priority patent/CA1012958A/en
Priority to JP49097473A priority patent/JPS6124436B2/ja
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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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
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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
    • C10M2207/027—Neutral salts thereof
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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
    • C10M2207/028—Overbased salts thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • 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
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • 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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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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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
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    • C10N2010/00—Metal present as such or in compounds
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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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02F—CYLINDERS, PISTONS OR CASINGS, FOR COMBUSTION ENGINES; ARRANGEMENTS OF SEALINGS IN COMBUSTION ENGINES
    • F02F7/00—Casings, e.g. crankcases or frames
    • F02F7/006—Camshaft or pushrod housings

Definitions

  • ABSTRACT Lubricating oil compositions containing from about 0.01 to 5.0% of a tetra poly(oxyethylene)poly(oxypropylene) derivative of ethylenediamine having a molecular weight in the range of about 1650 to 15,000. These compositions are useful as engine oils, gear oils, hydraulic fluids and other industrial oils and exhibit improved rust inhibition properties as well as sludge elimination.
  • Tetronic series of tetra polyoxyalkyleneoxy derivatives of ethylenediamine are represented by the following general formula:
  • x and y are integers which are so selected that the average molecular weight range of the poly(oxypropylene) hydrophobe unit is between about 500 and 7000 and the poly(oxyethylene) hydrophilic unit constitutes from about 10 to 80% by weight of the total molecule.
  • the total molecular weight of these commercially available derivatives fall within the broad molecular weight range of 1650 to over 26,000.
  • those amine derivatives of the class described which have a total molecular weight within the range of about 5,000 to 12,500 and a poly (oxyethylene) content of from about 10 to 40%.
  • liquid or paste products which are readily soluble or dispersible in the lubricating oil base. These materials are well known in the art and may be produced by the process disclosed in US. Pat. No. 2,979,528.
  • compositions of the invention comprise a major amount of a lubricating oil, natural or synthetic, containing from about 0.01 to 5% by weight of a tetra poly(oxyethylene)-poly(oxypropylene) derivative of the formula given above, wherein x and y are so selected as to provide a total average molecular weight within the range of about 1650 to 15,000 and wherein the poly(oxyethylene) units constitute from about to about 50% by weight of the molecule.
  • the lubricating oil compositions of this invention may optionally contain additional conventional additives such as antioxidants; dispersants, especially ashless dispersants of the succinimide type; metal based detergents; corrosion inhibitors; extreme pressure agents, viscosity index improvers; pour point depressants and other conventional additives as desired.
  • additional conventional additives such as antioxidants; dispersants, especially ashless dispersants of the succinimide type; metal based detergents; corrosion inhibitors; extreme pressure agents, viscosity index improvers; pour point depressants and other conventional additives as desired.
  • hydraulic oil and gear oil formulations as well as engine oil formulations, containing a lubricating oil base and tetra poly(oxyethylene) poly (oxypropylene) derivative of ethylene diamine are within the scope of this invention.
  • the amine derivative may be incorporated with an SA-lOW to SA-4O weight lubricating oil to provide a suitable hydraulic oil having improved antisludging and anti-rust properties.
  • the lubricating oil base may be an animal or vegetable oil, mineral oil or synthetic oil, or mixture thereof.
  • castor oil is commonly used as a base component in hydraulic oils as well as in lubricating oils, and fatty oils such as lard oil, neatsfoot oil and sperm oil are used for special purpose lubricants and greases.
  • the composition of the invention will comprise a mineral lubricating oil or synthetic lubricating oil base and will be used as a hydraulic or engine oil.
  • Such lubricating base oils are well known in the art and are described in detail, for example, in the aforementioned US. Pat. No. 3,509,052 and in other published literature.
  • ashless dispersants may be of the ester or succinimide type which includes the esters, acidic esters, half-esters-half-amides, acidic amides, amidines, amine salts and metal salts of substituted succinic acids wherein the the substituent contains at least about fifty aliphatic carbon atoms.
  • ester or succinimide type which includes the esters, acidic esters, half-esters-half-amides, acidic amides, amidines, amine salts and metal salts of substituted succinic acids wherein the the substituent contains at least about fifty aliphatic carbon atoms.
  • reaction products of high molecular weight polyalkylene substituted succinic acids and anhydrides with ethylene polyamines such as described in US. Pat. No. 3,172,892 may be used. They may be used in the engine oil compositions in the desired dispersant amounts, e.g., up to about 10% by weight based on the total weight of the composition.
  • Metal containing detergents include the well known over-based alkaline earth metal salts such as the calcium, barium and magnesium salts of alkyl benzene sulphonic acids and of phosphosulphurized hydrocarbons, for example polyisobutylenes, and such basic additives as alkaline earth metal or magnesium alkyl phenates or their corresponding sulphurized derivatives. These additives may be used in the desired detergent amounts, e.g., about 0.5% to 7.5% by weight based on the total weight of the composition.
  • any of the known extreme pressure agents, corrosion-inhibiting and oxidation inhibiting agents may be used in the composition of the invention in amounts which usually comprise no more than about 0.1 to 5% by weight of the total weight of the composition.
  • Typical corrosion inhibitors are compounds of the Group II metals with sulphur and phosphorus, e.g., the barium and zinc phosphorodithionates.
  • the invention is in no way limited to the use of these specific materials.
  • EXAMPLE 1 An SAE 30 M1L-L-2104C type oil containing a conventional calcium, barium and zinc detergent inhibitor
  • EXAMPLE 7 An oil as in Example 6, but with 0.05% wt. of Tetronic 1501 added.
  • the base stock was a Middle East Solvent refined 95V] stock, and the blended oil had the following analysis:
  • Tetronic 1101 is a tetra poly(oxyethylene)-poly(oxypropylene) derivative of ethylene diamine of the given formula which has a total molecular weight of 5600 and a poly(oxyethylene) content of about by weight based on the total weight of the molecule.
  • EXAMPLE 3 An oil as in Example 1, but with 0.1% wt. of Tetronic 1 101 added.
  • Tetronic 1501 is a derivative of the given formula which has an average molecular weight of 7900 and a poly(oxyethylene) content of about 10%.
  • Tetronic 1304 is a derivative of the given formula which has an average molecular weight of 10,500 and a poly(oxyethylene) content of about 40%.
  • EXAMPLE 6 Another area of performance in which the alkoxylated amines of the present invention offer benefits is in the control of rocker cover emulsion sludge.
  • This emulsion sludge is usually an oil in water emulsion and it is formed by the mechanical agitation of oil and water produced by condensation of blowby gases in the rocker box area.
  • This emulsion sludge can be formed under various conditions, but it is usually accentuated by low ambient temperatures and stop-start driving conditions.
  • EXAMPLE 8 An SAE l0W/30 MIL-L-46l52 type oil containing a conventional calcium and zinc detergent inhibitor system, a succinimide type ashless dispersant and a conventional non-dispersant methacrylate V1 improver was formulated using a solvent refined Middle East Vl base stock.
  • the blended oil had the following analysis:
  • EXAMPLE 9 An oil as in Example 8, but with 0.025% wt. Tetronic 1 101 added.
  • EXAMPLE 10 An oil as in Example 8, but with 0.025% wt. Tetronic l 101 added.
  • Tetronic 1301 is an amine derivative of the given formula which has a total molecular weight of 6800 and a poly(oxyethylene) content of about 10%.
  • EXAMPLE 13 An oil as in Example 8, but with 0.25% wt. Tetronic 1501 added.
  • EXAMPLE 14 An oil as in Example 8, but with 0.037% wt. Tetronic 1501 added.
  • EXAMPLE 15 An oil as in Example 8, but with 0.05% wt. Tetronic 1501 added.
  • Tetronic 904 is an amine derivative of the given formula which has a molecular weight of 7500 and a poly- (oxyethylene) content of about 40%.
  • Tetronic 1104 is an amine derivative of the given formula which has a molecular weight of 8300 and a poly(oxyethylene) content of about 40%.
  • Tetronic 1302 is an amine derivative of the given formula having a molecular weight of 7800 and a poly(oxyethylene) content of about 20%.
  • Tetronic 1504 is an amine derivative of the given formula having a molecular weight of 12,500 and a poly- (oxyethylene) content of about 40%.
  • EXAMPLE 17 An SAE l0W/30 MlL-L-46l52 type oil containing a non-dispersant VI improver and a conventional calcium, zinc and magnesium detergent inhibitor system and a conventional calcium, zinc and magnesium detergent inhibitor system with succinimide type ashless dispersant was evaluated with various demulsibility A hydraulic oil containing 0.06% Zn, 0.06% P, 0.10% S, and 0.07% Ca was tested for demulsibility according to ASTM Method D-140l whereby the time of separation of a warm, previously stirred emulsion of 40 ml. of water and 40 ml. of oil is measured. The effect of variagents by the ASTM D-1401 method.
  • Tetronic 701 is an amine derivative of the given formula having a molecular weight of 3600 and a poly (oxyethylene) content of 10%.
  • EXAMPLE 19 In addition to evaluating the Tetronic products in gear lubricants using the ASTM D-2711 method, two ethoxylated amines were evaluated. The results show that the ethoxylated amines produce considerable emulsion and are inferior to the Tetronic products.
  • a MIL-L-46152 type oil containing a conventional nondispersant VI irnprover and succinimide type ashless dispersant together with a calcium, magnesium and zinc detergent-inhibitor system containing Ca 0.06%, Zn 0.13% and Mg 0.09% was formulated.
  • a lubricating composition comprising a major amount of an oil of lubricating viscosity and conventional additives selected from the group consisting of internal combustion engine oil additives, gear oil additives and hydraulic oil additives in an amount sufficient to effect each additives attendant function, the improvement comprising as a further additive from 0.01 to 5.0 percent of a tetra poly (oxyethylene) poly (oxypropylene) derivative of ethylenediamine having the formula,
  • x and y are so selected that said derivative has a molecular weight in the range of from about 1650 to 15,000 and a poly( oxyethylene) content of about 10 to 2.
  • additives comprise an ashless dispersant selected from the group consisting of the metal salts, amine salts, amides, imides, amidines, and esters of substituted succinic acids having a substitutent containing at least about 50 aliphatic carbon atoms.

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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)
US391469A 1973-08-24 1973-08-24 Lubricating oil compositions of improved rust inhibition Expired - Lifetime US3928219A (en)

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US391469A US3928219A (en) 1973-08-24 1973-08-24 Lubricating oil compositions of improved rust inhibition
GB36609/74A GB1483513A (en) 1973-08-24 1974-08-20 Lubricating oil compositions
FR7428678A FR2248316B1 (ja) 1973-08-24 1974-08-21
DE2440531A DE2440531A1 (de) 1973-08-24 1974-08-23 Schmiermittelgemisch, seine verwendung als hydraulikfluessigkeit und additivkonzentrat zu seiner herstellung
BE147863A BE819142A (fr) 1973-08-24 1974-08-23 Conpositions d'huiles lubrifiantes et de fluides hydrauliques
NL7411260.A NL162131C (nl) 1973-08-24 1974-08-23 Werkwijze ter bereiding van een smeermiddel- samenstelling.
IT26572/74A IT1020169B (it) 1973-08-24 1974-08-23 Composizioni di oli lubrificanti
CA207,716A CA1012958A (en) 1973-08-24 1974-08-23 Lubricating oil compositions
JP49097473A JPS6124436B2 (ja) 1973-08-24 1974-08-23

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Cited By (8)

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US4278555A (en) * 1978-11-15 1981-07-14 Ethyl Corporation Lubricant composition
US4305834A (en) * 1980-01-02 1981-12-15 Ethyl Corporation Lubricating composition containing emulsion-sludge inhibitors
US4317741A (en) * 1981-01-29 1982-03-02 Olin Corporation Use of poly(oxyalkylated) hydrazines as corrosion inhibitors
US4552686A (en) * 1984-04-09 1985-11-12 Texaco Inc. Corrosion inhibiting composition and method
US4636323A (en) * 1983-11-24 1987-01-13 Nippon Oil And Fats Co., Ltd. Lubricating oil composition for metal rolling
US5747430A (en) * 1994-07-28 1998-05-05 Exxon Research And Engineering Company Lubricant composition
US5957005A (en) * 1997-10-14 1999-09-28 General Electric Company Wire drawing die with non-cylindrical interface configuration for reducing stresses
US6001071A (en) * 1998-02-06 1999-12-14 Butler; Brian R. Aquatic exercise and rehabilitation device

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JPS5821958B2 (ja) * 1978-03-28 1983-05-04 三洋化成工業株式会社 水↓−グリコ−ル系不燃性作動液
BR8701840A (pt) * 1986-04-21 1988-01-26 Nisshin Oil Mills Ltd Oleo de laminagem a frio para placas de aco
WO2023190361A1 (ja) * 2022-03-30 2023-10-05 出光興産株式会社 潤滑油組成物、並びに潤滑油組成物の使用方法及び製造方法

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US2510063A (en) * 1948-07-20 1950-06-06 Hercules Powder Co Ltd Corrosion inhibitor
US3005776A (en) * 1959-12-31 1961-10-24 Union Carbide Corp Hydraulic fluid composition
US3117931A (en) * 1955-08-01 1964-01-14 Exxon Research Engineering Co Inhibitors for oleaginous compositions
US3203904A (en) * 1962-09-24 1965-08-31 Betz Laboratories Corrosion inhibition for flowing steam and condensate lines
US3235501A (en) * 1962-06-11 1966-02-15 Socony Mobil Oil Co Inc Foam-inhibited oil compositions
US3464925A (en) * 1965-10-15 1969-09-02 Progil Hydraulic fluids containing aminotriols and derivatives thereof
US3657129A (en) * 1969-05-05 1972-04-18 Economics Lab Lubricating compositions
US3794586A (en) * 1971-03-18 1974-02-26 Nippon Oil Co Ltd Lubricating oil composition
US3801506A (en) * 1971-07-12 1974-04-02 Texaco Inc Water-resistant greases

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US2510063A (en) * 1948-07-20 1950-06-06 Hercules Powder Co Ltd Corrosion inhibitor
US3117931A (en) * 1955-08-01 1964-01-14 Exxon Research Engineering Co Inhibitors for oleaginous compositions
US3005776A (en) * 1959-12-31 1961-10-24 Union Carbide Corp Hydraulic fluid composition
US3235501A (en) * 1962-06-11 1966-02-15 Socony Mobil Oil Co Inc Foam-inhibited oil compositions
US3203904A (en) * 1962-09-24 1965-08-31 Betz Laboratories Corrosion inhibition for flowing steam and condensate lines
US3464925A (en) * 1965-10-15 1969-09-02 Progil Hydraulic fluids containing aminotriols and derivatives thereof
US3657129A (en) * 1969-05-05 1972-04-18 Economics Lab Lubricating compositions
US3794586A (en) * 1971-03-18 1974-02-26 Nippon Oil Co Ltd Lubricating oil composition
US3801506A (en) * 1971-07-12 1974-04-02 Texaco Inc Water-resistant greases

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4278555A (en) * 1978-11-15 1981-07-14 Ethyl Corporation Lubricant composition
US4305834A (en) * 1980-01-02 1981-12-15 Ethyl Corporation Lubricating composition containing emulsion-sludge inhibitors
US4317741A (en) * 1981-01-29 1982-03-02 Olin Corporation Use of poly(oxyalkylated) hydrazines as corrosion inhibitors
US4636323A (en) * 1983-11-24 1987-01-13 Nippon Oil And Fats Co., Ltd. Lubricating oil composition for metal rolling
US4552686A (en) * 1984-04-09 1985-11-12 Texaco Inc. Corrosion inhibiting composition and method
US5747430A (en) * 1994-07-28 1998-05-05 Exxon Research And Engineering Company Lubricant composition
US5957005A (en) * 1997-10-14 1999-09-28 General Electric Company Wire drawing die with non-cylindrical interface configuration for reducing stresses
US6314836B1 (en) 1997-10-14 2001-11-13 General Electric Company Wire drawing die with non-cylindrical interface configuration for reducing stresses
US6001071A (en) * 1998-02-06 1999-12-14 Butler; Brian R. Aquatic exercise and rehabilitation device

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IT1020169B (it) 1977-12-20
DE2440531A1 (de) 1975-03-06
BE819142A (fr) 1974-12-16
NL162131B (nl) 1979-11-15
JPS5051104A (ja) 1975-05-07
JPS6124436B2 (ja) 1986-06-11
GB1483513A (en) 1977-08-24
NL162131C (nl) 1980-04-15
NL7411260A (nl) 1975-02-26
CA1012958A (en) 1977-06-28
DE2440531C2 (ja) 1990-09-06
FR2248316A1 (ja) 1975-05-16
FR2248316B1 (ja) 1981-05-29

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