EP0535990A1 - Schmierölzusammensetzung - Google Patents

Schmierölzusammensetzung Download PDF

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Publication number
EP0535990A1
EP0535990A1 EP92309033A EP92309033A EP0535990A1 EP 0535990 A1 EP0535990 A1 EP 0535990A1 EP 92309033 A EP92309033 A EP 92309033A EP 92309033 A EP92309033 A EP 92309033A EP 0535990 A1 EP0535990 A1 EP 0535990A1
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EP
European Patent Office
Prior art keywords
carbon atoms
weight
ester
fatty acid
straight
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.)
Granted
Application number
EP92309033A
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English (en)
French (fr)
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EP0535990B1 (de
Inventor
Mineo Kagaya
Mitsuaki Ishimaru
Hiroaki Ishii
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Eneos Corp
Original Assignee
Nippon Oil Corp
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Publication of EP0535990A1 publication Critical patent/EP0535990A1/de
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    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/02—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a non-macromolecular organic compound
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    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/089—Overbased salts
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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
    • C10N2030/64—Environmental friendly compositions
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    • C10N2040/20—Metal working
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    • C10N2040/25—Internal-combustion engines
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    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol-fuelled engines
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    • C10N2040/255—Gasoline engines
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    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/26—Two-strokes or two-cycle engines
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B77/00—Component parts, details or accessories, not otherwise provided for
    • F02B77/04—Cleaning of, preventing corrosion or erosion in, or preventing unwanted deposits in, combustion engines

Definitions

  • the present invention relates to a lubricating oil composition and more particularly to a lubricating oil composition which is excellent in biodegradability, high-temperature cleanliness and anti-seizure performance and is therefore conductive to environmental protection.
  • Two-cycle engines raise problems as to possible environmental pollution since they discharge an unburned engine oil as an accompaniment of their exhaust gases due to their lubrication mechanism.
  • outboard engines used in rivers, lakes or oceans discharge exhaust gases containing unburned oil into the water thereby to raise problems as to water pollution due to the unburned oil.
  • Chain saws and other forestry machinery may also cause the polution of forests and rivers due to the unburned oil.
  • An object of the present invention is to provide a lubricating oil having excellent performances in biodegradability, high-temperature cleanliness, lubricity and anti-seizure performance.
  • Another object is to provide a method for lublication comprising the use of such a lubricating oil as above.
  • the present inventors made intensive studies to aim mainly at solving the above problems and, as the result of their studies, they found out that a lubricating oil comprising predetermined esters as main components satisfies the above-mentioned requirements, thus achieving the present invention.
  • a lubricating oil composition comprises as the main component an ester mixture consisting of (A) 60 - 95 % by weight of an ester of a hindered alcohol with a straight-chain saturated fatty acid having 8 - 12 carbon atoms, and (B) 5 - 40 % by weight of a complex ester of a hindered alcohol with a straight-chain saturated fatty acid having 8 - 12 carbon atoms and also with a dibasic acid having 2 - 50 carbon atoms.
  • a lubricating oil composition comprises (I) 100 parts by weight of an ester mixture consisting essentially of (A) 60 - 95 % by weight of an ester of a hindered alcohol and a straight-chain saturated fatty acid having 8 - 12 carbon atoms, and (B) 5 - 40 % by weight of a complex ester of a hindered alcohol with both a straight-chain saturated fatty acid having 8 - 12 carbon atoms and a dibasic acid having 2 - 50 carbon atoms, and (II) not more than 30 parts by weight of a hydrocarbon-based solvent and/or a lubricating base oil.
  • the ester mixture used in the present invention as the main ingredient is a mixture of (A) an ester of a hindered alcohol and a straight-chain saturated fatty acid having 8 - 12 carbon atoms, and (B) a complex ester of a hindered alcohol with both a straight-chain saturated fatty acid having 8 - 12 carbon atoms and a dibasic acid having 2 - 50 carbon atoms.
  • the hindered alcohol used means one in which the ⁇ carbon atom of the hydroxyl group is a quarternary carbon atom. More specifically, the hindered alcohol preferably used include dihydric to tetrahydric alcohols having 5 - 10 carbon atoms, and a dimer and trimer thereof, and they are exemplified by neopentyl glycol, 2-methyl-2-propyl-1, 3- propanediol, trimethylol ethane, trimethylol propane (TMP), trimethylol butane, pentaerythritol (PET), di- (trimethylol propane), tri-(trimethylol propane), di- (pentaerythritol) and tri-(pentaerythritol).
  • the straight-chain saturated fatty acid having 8 - 12 carbon atoms used in the present invention include caprylic acid, pelargonic acid, capric acid and lauric acid. Furthermore, such fatty acids may be used in the form of a derivative such as an acid anhydride, acid halide and metal salt of the acids. In the preparation of the component (A), at least two different acids among these fatty acids may be esterified with the same hindered alcohol, or the resulting ester may have a hydroxyl group therein which remains without being esterified.
  • the same hindered alcohol and the saturated fatty acid having 8 - 12 carbon atoms as those used in the preparation of the above component (A) may be employed.
  • the dibasic acids having 2 - 50 carbon atoms used in said preparation include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimeric acid, suberic acid, azelaic acid and sebacic acid, as well as other acids having more carbon atoms than the above-mentioned acids.
  • these acids those having 6 - 40 carbon atoms are desirably used.
  • the component (B) may be exemplified by a complex ester represented by the following general formula (I).
  • X1 to X4 may be identical with or different from each other and each represent an alkyl group having 1 - 4 carbon atoms or a group having the following general formula of -CH2-OCO-R4 (R4 being an alkyl group having 7 - 11 carbon atoms).
  • R1 represents an alkylene or alkenylene group having 1 - 48 carbon atoms with the proviso that when the number of carbon atoms of a dibasic acid is 2, R1 does not exist in the formula I.
  • R2 to R4 may be identical with or different from each other and each represent a straight-chain alkyl group having 7 - 11 carbon atoms.
  • R1 corresponds to the alkylene group of a dibasic acid having 3 - 50 carbon atoms
  • R2 to R4 each correspond to the alkyl group of a straight-chain saturated fatty acid having 8 - 12 carbon atoms.
  • the content of the above component (A) is 60 to 95%, preferably 70 to 90%, by weight based on the total weight of the specific base oil.
  • the content of the above component (B) is 5 to 40%, preferably 10 to 30%, by weight based on the total weight of the specific base oil.
  • the resulting composition will not be appropriate in viscosity.
  • the content of the above component (B) exceeds 40% by weight, the resulting composition will undesirably be insufficient in biodegradability.
  • the composition of the present invention shoud have a kinematic viscosity of preferably 6 to 15 mm2/s at a temperature of 100 °C.
  • the lubricating oil composition of the present invention may contain the above ester mixture alone, and, however, it may further contain a known hydrocarbon-based solvent and/or a known lubricating base oil as required.
  • This hydrocarbon-based solvent may be one which is usually used for two-cycle engine oils, and it is exemplified by a petroleum-based hydrocarbon solvent and/or a synthesized hydrocarbon solvent each having a boiling point of 150 to 300 °C at atmospheric pressure. Specifically, these solvents are illustrated by Stoddard solvent, mineral spirits, kerosene fractions, n-paraffins, i-paraffins and propylene oligomers.
  • the lubricating base oil may be one which is usally used as a base oil for lubricating oils and it is exemplified by paraffinic and naphthenic mineral oils prepared by refining lubricating oil fractions which are obtained by distilling crude oils under atmospheric or a reduced pressure; poly- ⁇ -olefin (1-octene oligomer, 1-decene oligomer, etc.); polybutene, alkylbenzenes; alkylnaphthalenes; polyglycol; diester (ditridecylgultarate, di,2-ethylhexyl adipate); diisodecyl adipate; di,tridecyl adipate; di,2-ethyl hexyl cebacate; esters of polyol with a straight-chain chain fatty acid having up to 7 or at least 13 carbon atoms or with a branched-chain fatty acid (trimethylolpropane stea
  • the solvent and/or a lubricating base oil other than the above-mentioned ester mixture are/is to be added to the ester mixture
  • composition of this invention may be incorporated with various kinds of known additives for the purpose of further improving the performance of the composition, as required.
  • the additives include basic calcium sulfonate, basic calcium phenate, basic calcium salicylate, alkenyl succinic acid imide, benzyl amine, a detergent such as a polyalkenyl amine, a pour point depressant such as polymethacrylate, a rust preventing agent and anti-foaming agent.
  • additives may be added alone or jointly. They may be added in any optional amount and, usually, they may each be added in an amount of up to 30, preferably 0.5 - 15, parts by weight per 100 parts by weight of the specific base oil.
  • the lubricating oil compositions of this invention are suited especially for two-cycle engines such as outboards and chain saws since they are excellent in biodegradability, they are preferably used in engines for two-wheeled vehicles such as mopet (motorlike) and motorcycles, and in portable power unit engines for lawnmowers and power generators. Furthermore, they can be used as a four-cycle engine oil, a hydraulic oil, a gear oil and a metal processing oil.
  • biodegradability and thermal stability The biodegradability and thermal stability which are fundamental performances of this invention were evaluated.
  • the biodegradability was measured by the coulometer method using a closed-system oxygen consumption measurement apparatus, and this method is usually called the MITI method which is one of the test methods prescribed by the Chemical Substances Control Law in Japan. This method is the one in which incubation is effected at a temperature of 25°C for a period of time of 14 days.
  • a decomposition degree is represented by the following formula.
  • Decomposition degree [(BOD-B)/TOD] X 100
  • BOD Biological Oxygen Demand of a test substance (Value found, mg)
  • B Oxygen consumption of a culture medium into which activated sludge has been inoculated (Value found, mg)
  • TOD Theoretical Oxygen Demand required for complete oxidation of the test substance (Value calculated, mg). The value for TOD was determined by calculating the molecular formula obatined from the elemental analysis of the test substance (oil).
  • a test substance which showed a decomposition degree of 35 to 40 % in this test is considered to have undergone almost complete biodegradation, and, therefore, the biodegradability standard for the compositions of this invention has been determined in conformity with said decomposition degree.
  • HTT hot tube test
  • Example 3 As shown in Table 2, the composition of this invention in Example 3 was excellent in anti-seizure performance between the piston and the cylinder as compared with Comparative Examples 7 and 8 which were commercially-available biodegradable two-cycle engine oils. This composition of Example 3 was also extremely excellent in piston cleanliness without ring sticking after the test. Table 2 Test oils Ex. 3 Comp. Ex. 7 Comp. Ex.
  • Example 4 As shown in Table 3, the composition of Example 4 according to this invention was excellent in piston cleanliness without causing ring sticking as compared with Comparative Example 7 which was a commercially available biodegradable two-cycle engine oil and with Comparative Example 8 which has a mineral base oil. The composition of Example 4 was also extremely low in cylinder head deposits. Table 3 Test oils Ex. 4 Comp. Ex. 7 Comp. Ex.10 ring sticking, top ring 10 8 10 second ring 10 10 10 ring land, top 6.7 1.0 1.6 second 8.2 5.3 4.4 piston skart 10 9.3 9.2 undercrown 10 2.2 1.6 cylinder head 10 8.9 5.7 Total: 70 points (full marks) 64.9 44.7 42.5
  • An engine cleanliness test was carried out on a 1-cylinder engine used for a chain saw engine and having a displacement of 45 cc, under conditions of an engine speed of 9000rpm, full engine load, a plug gasket temperature of 280°C, a fuel oil mixing ratio of 50:1 and testing time of 30 hrs (mixing lubrication).
  • Example 4 As shown in Table 4, the composition of Example 4 according to this invention was extremely excellent in ring sticking resistance and piston cleanliness as compared with Comparative Example 11 which was an oil for a commercially-available low-smoke type two-cycle engine oil.
  • Table 4 Test oils Ex. 4 Comp. Ex. 11 ring sticking, top ring 7.0 5.0 second ring 10 10 ring land, top 8.4 3.9 second 9.5 5.2 piston skart 10 9.0 undercrown 2.4 0.9 Total: 60 points (full marks) 47.3 34.0
  • composition according to this invention has already passed the TC-WII which is a standard of NMMA (National Marine Manufacturers Association) for two-cycle engine oils for use in outboard engines and has also passed the CEC L-33-T-82 which is a test method of evaluating biodegradability of two-cycle engine oils for outboard engines (the method of biodegradability test is different from the MITI method of Japan) and which indicates that a standard of the biodegradability is at least 67 % (for example, Example 4 exhibited a decomposition degree of 87 %, and, on the other hand, Comparative Example 7 showed 67 % in this test method).
  • NMMA National Marine Manufacturers Association
  • the composition according to this invention is a lubricating oil which can solve the problems as to the piston ring sticking and piston seizure which have become problems in the market.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
EP92309033A 1991-10-04 1992-10-02 Schmierölzusammensetzung Expired - Lifetime EP0535990B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP284083/91 1991-10-04
JP3284083A JP2872465B2 (ja) 1991-10-04 1991-10-04 潤滑油組成物

Publications (2)

Publication Number Publication Date
EP0535990A1 true EP0535990A1 (de) 1993-04-07
EP0535990B1 EP0535990B1 (de) 1997-01-02

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Country Status (5)

Country Link
EP (1) EP0535990B1 (de)
JP (1) JP2872465B2 (de)
AT (1) ATE147096T1 (de)
CA (1) CA2079512A1 (de)
DE (1) DE69216346D1 (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0572273A1 (de) * 1992-05-29 1993-12-01 Tonen Corporation Dispergatoren enthaltende Schmierölzusammensetzungen für Zweitaktmotoren
DE4217961A1 (de) * 1992-05-30 1993-12-02 Fuchs Petrolub Ag Oel & Chemie Umweltverträgliche und biologisch schnell aubbaubare Betriebsstoffe zur Umlaufschmierung von Motoren und sonstigen Aggregaten in Fahrzeugen und Arbeitsmaschinen
WO1994025548A1 (de) * 1993-04-28 1994-11-10 Henkel Kommanditgesellschaft Auf Aktien Hydrauliköle mit verbesserter dichtungsverträglichkeit
EP0652280A2 (de) * 1993-10-15 1995-05-10 Oronite Japan Limited Mehrzwecke funktionelle Flüssigkeit für landwirtschaftliche Maschine oder Baumaschine
EP0656931A1 (de) * 1992-08-28 1995-06-14 Henkel Corporation Biologisch abbaubare dieselmotorölzusammensetzungen und esterhaltige basisöle
WO1995018201A1 (en) * 1993-12-30 1995-07-06 Exxon Chemical Patents Inc. Biodegradable two-cycle oil composition
US5817607A (en) * 1994-12-08 1998-10-06 Exxon Chemical Patents Inc. Biodegradable branched synthetic ester base stocks and lubricants formed therefrom
WO1999016849A1 (en) * 1997-10-01 1999-04-08 Unichema Chemie B.V. Complex esters, formulations comprising these esters and use thereof
FR2792325A1 (fr) * 1999-06-30 2000-10-20 Renault Fluides fonctionnels de non toxiques et biodegradables a base d'esters a chaines grasses de neopolyols pour vehicules automobiles
EP2428552B1 (de) 2009-05-08 2015-07-01 Idemitsu Kosan Co., Ltd. Biologisch abbaubare schmiermittelzusammensetzung

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000044972A (ja) * 1998-08-03 2000-02-15 General Sekiyu Kk 潤滑剤の生分解性を向上させる方法、生分解性向上剤および生分解性潤滑剤組成物
WO2005077876A1 (ja) 2004-01-28 2005-08-25 Idemitsu Kosan Co., Ltd. 長鎖分岐アルキル基含有カルボニル化合物

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3218256A (en) * 1959-01-14 1965-11-16 Castrol Ltd Lubricating compositions
US3505230A (en) * 1967-03-29 1970-04-07 Monsanto Co Functional ester base fluids containing corrosion inhibitors
FR2144559A1 (de) * 1971-07-05 1973-02-16 Inst Francais Du Petrole
FR2311088A1 (fr) * 1975-05-15 1976-12-10 Inst Francais Du Petrole Nouvelles compositions d'esters de trimethylolpropane et leur utilisation dans la lubrification des moteurs 2 temps
DE2551173A1 (de) * 1975-11-14 1977-05-26 Henkel & Cie Gmbh Hochviskose, neutrale komplexester
EP0410170A1 (de) * 1989-07-25 1991-01-30 Profi-Gas Ltd. Flüssiges Treibstoffgemisch, Verfahren zu seiner Herstellung und seine Verwendung für Zweitaktmotoren
EP0435253A1 (de) * 1989-12-28 1991-07-03 Nippon Oil Company, Limited Kühlschranköle zum Gebrauch mit Hydrogen enthaltenden Halogenocarbonkühlmitteln

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3218256A (en) * 1959-01-14 1965-11-16 Castrol Ltd Lubricating compositions
US3505230A (en) * 1967-03-29 1970-04-07 Monsanto Co Functional ester base fluids containing corrosion inhibitors
FR2144559A1 (de) * 1971-07-05 1973-02-16 Inst Francais Du Petrole
FR2311088A1 (fr) * 1975-05-15 1976-12-10 Inst Francais Du Petrole Nouvelles compositions d'esters de trimethylolpropane et leur utilisation dans la lubrification des moteurs 2 temps
DE2551173A1 (de) * 1975-11-14 1977-05-26 Henkel & Cie Gmbh Hochviskose, neutrale komplexester
EP0410170A1 (de) * 1989-07-25 1991-01-30 Profi-Gas Ltd. Flüssiges Treibstoffgemisch, Verfahren zu seiner Herstellung und seine Verwendung für Zweitaktmotoren
EP0435253A1 (de) * 1989-12-28 1991-07-03 Nippon Oil Company, Limited Kühlschranköle zum Gebrauch mit Hydrogen enthaltenden Halogenocarbonkühlmitteln

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5547597A (en) * 1992-05-29 1996-08-20 Tonen Corporation Lubricating oil composition for two-cycle engines
EP0572273A1 (de) * 1992-05-29 1993-12-01 Tonen Corporation Dispergatoren enthaltende Schmierölzusammensetzungen für Zweitaktmotoren
DE4217961A1 (de) * 1992-05-30 1993-12-02 Fuchs Petrolub Ag Oel & Chemie Umweltverträgliche und biologisch schnell aubbaubare Betriebsstoffe zur Umlaufschmierung von Motoren und sonstigen Aggregaten in Fahrzeugen und Arbeitsmaschinen
EP0572866A1 (de) * 1992-05-30 1993-12-08 Fuchs Petrolub Ag Oel + Chemie Umweltverträgliche und biologisch schnell abbaubare Betriebsstoffe zur Umlaufschmierung von Motoren und sonstigen Aggregaten in Fahrzeugen und Arbeitsmaschinen
EP0656931A1 (de) * 1992-08-28 1995-06-14 Henkel Corporation Biologisch abbaubare dieselmotorölzusammensetzungen und esterhaltige basisöle
EP0656931A4 (de) * 1992-08-28 1997-05-02 Henkel Corp Biologisch abbaubare dieselmotorölzusammensetzungen und esterhaltige basisöle.
WO1994025548A1 (de) * 1993-04-28 1994-11-10 Henkel Kommanditgesellschaft Auf Aktien Hydrauliköle mit verbesserter dichtungsverträglichkeit
EP0652280A2 (de) * 1993-10-15 1995-05-10 Oronite Japan Limited Mehrzwecke funktionelle Flüssigkeit für landwirtschaftliche Maschine oder Baumaschine
EP0652280A3 (de) * 1993-10-15 1995-06-21 Oronite Japan Limited Mehrzwecke funktionelle Flüssigkeit für landwirtschaftliche Maschine oder Baumaschine
WO1995018201A1 (en) * 1993-12-30 1995-07-06 Exxon Chemical Patents Inc. Biodegradable two-cycle oil composition
US5817607A (en) * 1994-12-08 1998-10-06 Exxon Chemical Patents Inc. Biodegradable branched synthetic ester base stocks and lubricants formed therefrom
WO1999016849A1 (en) * 1997-10-01 1999-04-08 Unichema Chemie B.V. Complex esters, formulations comprising these esters and use thereof
US6462001B1 (en) 1997-10-01 2002-10-08 Unichema Chemie Bv Complex esters, formulations comprising these esters and use thereof
MY119806A (en) * 1997-10-01 2005-07-29 Unichema Chemie Bv Esters, formulations comprising these esters and use thereof
FR2792325A1 (fr) * 1999-06-30 2000-10-20 Renault Fluides fonctionnels de non toxiques et biodegradables a base d'esters a chaines grasses de neopolyols pour vehicules automobiles
EP2428552B1 (de) 2009-05-08 2015-07-01 Idemitsu Kosan Co., Ltd. Biologisch abbaubare schmiermittelzusammensetzung

Also Published As

Publication number Publication date
JPH0598276A (ja) 1993-04-20
CA2079512A1 (en) 1993-04-05
EP0535990B1 (de) 1997-01-02
ATE147096T1 (de) 1997-01-15
DE69216346D1 (de) 1997-02-13
JP2872465B2 (ja) 1999-03-17

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