EP0416914A1 - Schmierölzusammensetzungen - Google Patents

Schmierölzusammensetzungen Download PDF

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Publication number
EP0416914A1
EP0416914A1 EP90309748A EP90309748A EP0416914A1 EP 0416914 A1 EP0416914 A1 EP 0416914A1 EP 90309748 A EP90309748 A EP 90309748A EP 90309748 A EP90309748 A EP 90309748A EP 0416914 A1 EP0416914 A1 EP 0416914A1
Authority
EP
European Patent Office
Prior art keywords
oils
alpha
naphthylamine
lubricating oil
propylene
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
EP90309748A
Other languages
English (en)
French (fr)
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EP0416914B1 (de
Inventor
Hiroyuki Takashima
Noboru Ishida
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.)
Eneos Corp
Original Assignee
Nippon Oil Corp
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Publication date
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Publication of EP0416914A1 publication Critical patent/EP0416914A1/de
Application granted granted Critical
Publication of EP0416914B1 publication Critical patent/EP0416914B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
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    • 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
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/022—Well-defined aliphatic compounds saturated
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/36—Release agents or mold release agents
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • This invention relates to lubricating oil compositions utilizable as a lubricant in various industrial fields and more particularly to lubricating oil compositions which have good oxidation stability and in which sludges only form with difficulty.
  • antioxidants are added to the mineral oils or synthetic oils, however, the resulting lubricating oil compositions will exhibit high oxidation stability.
  • an undesirable problem involved in these compositions is that the solubility of antioxidants in the oils is low. Antioxidants will invariably be degraded when they are oxidized during their use, and the degradation products formed by oxidation will raise a problem if they are left as a sludge.
  • phenyl-alpha-naphthylamine is known as a good antioxidant, it has the drawback that its own solubility is low; further, the substances produced by its oxidation, as well as dimers, trimers and other oligomers of the naphthylamine are also disadvantageous because of low solubility. Accordingly, even when high oxidation stability is required, the naphthylamine which has high oxidation stability cannot be used in large amounts in order to improve the oxidation stability of lubricating oils.
  • GB-A-1,552,720 discloses a process of alkylating the phenyl group of the naphthylamine with a propylene trimer.
  • United States Patent No. 3,696,851 discloses a process of alkylating with a propylene dimer or an isobutylene dimer or trimer.
  • alkylated N-alkylphenyl-alpha-naphthylamines obtained by alkylation of the phenyl groups with a propylene or isobutylene dimer or trimer exhibit an improved solubility in oils, but they have the disadvantage that the solubility of the substances produced by oxidation is still low.
  • Diphenylamines are also excellent antioxidants, e.g, p,p′-di-t-octyldiphenylamine having a t-octyl group is known for this purpose.
  • p,p′-di-t-octyldiphenylamine having a t-octyl group is known for this purpose.
  • its oligomers like phenyl-alpha-naphthylamine have insufficient solubility.
  • Japanese Patent Laid-Open Gazette No. Sho. 59-5146 discloses an alkyldiphenylamine having a branched chain dodecyl group, a method for the production thereof and compositions including said amine. Said alkyldiphenylamines and compositions are also insufficiently effective in preventing oxidation and suppressing sludge formation.
  • An object of the present invention is to provide a lubricating oil composition which has higher oxidation stability than such compositions have had hither to and to suppress the formation of sludges.
  • the present inventors have made intensive studies to improve the sludge formation suppressing effect and oxidation stability of antioxidant by products and, as the result of the studies, they found that a lubricating oil composition including as additives an alkylphenyl-­alpha-naphthylamine and alkyldiphenylamine respectively having specific structures and used in respective amounts has very high oxidation stability and lessens sludge formation therein, thus completing the present invention.
  • a lubricating oil composition which comprises (I) a base oil selected from mineral oils having an aromatic content not higher than 30 wt.%, synthetic oils having no aromatic rings in the structural units, and mixtures thereof, (II) 0.01 to 5.0 wt.%, based on the total composition, of an N-p-alkylphenyl-alpha-naphthylamine of the general formula in which R1 represents a branched alkyl group having 12 or 15 carbon atoms and is derived from an oligomer of propylene, and (III) 0.01 to 5.0 wt.%, based on the total composition, of a p,p′-dialkyldiphenylamine of the general formula in which R2 and R3 may be identical with, or different from, each other and each represents a branched alkyl group having 12 or 15 carbon atoms which is derived from oligomers of propylene.
  • the base oils used in the present invention should be mineral oils having an aromatic content of 30 wt.% or less and/or synthetic oils which do not contain any aromatic rings in the structural units.
  • the mineral oils suitable for the purpose of the invention have generally a kinematic viscosity at 40 o C of from 5 to 10,000 centistokes, preferably from 10 to 10,000 centistokes, more preferably 20 to 1,000 centistokes.
  • the preferable mineral oils used herein are those produced by subjecting lubricating oil fractions obtained by distillation of crude oils, to a suitable refining treatment such as refining with a solvent, treatment with sulfuric acid, refining by hydrogenation of treatment with clay.
  • the preferable mineral oils should not have an aromatic content of more than 30 wt.%, preferably not more than 20 wt.%.
  • the aromatic content defined herein is intended to mean a value which is determined according to the method prescribed in ASTM D 2549-81.
  • the synthetic oils generally used in the practice of the invention should be those which are free of any aromatic rings in their structural units and which generally will have a kinematic viscosity at 40°C of from 10 to 10,000 centistokes.
  • the synthetic oils include: poly-alpha-olefin oils, such as polybutene and decene-1-oligomers, obtained by homopolymerization or copolymerization of alpha-olefins having from 4 to 30 carbon atoms; monoesters of aliphatic monocarboxylic acids and aliphatic monohydric alcohols, typical monoesters being butyl stearate and methyl laurate; diesters of aliphatic dibasic acids and aliphatic monohydric alcohols, such as di-2-ethylhexyl sebacate, dioctyl adipate and ditridecyl glutarate; aliphatic monocarboxylic acid esters of aliphatic polyhydric alcohols.
  • trimethylolpropane caprylate trimethylolpropane pelargonate and pentnaethritol 2-ethyl-hexanoate pentaerythritol and pelargonate
  • poly-alkylene glycols such as polyethylene glycol and polypropylene glycol, their monoalkyl ethers, dialkyl ethers, monoalkyl esters and dialkyl esters
  • cycloparaffins such as cyclododecane, hydrindane, bicyclohexyl and tercyclohexyl
  • alkylcycloparaffins such as dicyclohexylbutane and dicyclohexylpropane; and mixtures thereof.
  • the N-p-alkylphenyl-alpha-naphthylamine used in the present invention is a compound of the general formula in which R1 represents a branched alkyl group having 12 or 15 carbon atoms which is derived from an oligomer (tetramer or pentamer) of propylene.
  • the p,p′-dialkyldiphenylamine used in the present invention is a compound of the general formula in which R2 and R3 may be identical with, or different from, each other and each represent a branched alkyl group having 12 or 15 carbon atoms which is derived from an oligomer of propylene.
  • each of R1, R2 and R3 be a branched alkyl group derived from an oligomer of propylene. If such a branched alkyl group is derived from an alpha-olefin, the anti-oxidizing property of the resulting product will be very inferior to that of N-p-alkylphenyl-alpha-naphthylamine as the component (II) or p,p′-dialkyldiphenylamine as the component (III) used in the present invention. In addition, when such a branched alkyl group is derived from oligomers of olefins other than propylene, e.g. isobutylene, the resulting product itself is likely to precipitate by oxidation as a sludge when used in lubricating oils.
  • N-p-alkylphenyl-alpha-naphthylamine used as the component (II) and p,p′-dialkyldiphenylamine used as the component (III) in the practice of the invention can be prepared by any known techniques. In view of the ease of preparation, it is preferred to use a Friedel-Crafts alkylation reaction between phenyl-alpha-naphthylamine or diphenylamine and a propylene oligomer.
  • the catalysts usable in this reaction include metal halides such as aluminiumchloride, zinc chloride and iron chloride, as well as acid catalysts such as sulphuric acid, phosphoric acid, phosphorus pentoxide boron fluoride, acid clay and activated Clay.
  • the amount of each of the naphthylamine (II) and the diphenylamine (III) added should be from 0.01 to 5.0 wt.%, preferably from 0.1 to 3 wt.%, of the total composition. Amounts less than 0.01 wt.% are not desirable because hardly any effect is obtained. On the other hand, when the amount exceeds 5 wt.%, no further advantage is obtained and economical disadvantage is also incurred.
  • the lubricating oil composition of the invention may be incorporated with other additives ordinarily used for various purposes including, for example, antioxidants, detergent-dispersants, pour point depressants, viscosity index improvers, oiliness improvers, wear resistant agents, extreme pressure agents, corrosion inhibitors, metal-deactivators, antifoamers, emulsifiers, demulsifiers, bactericides and colorants.
  • additives are described in detail, for example, in "The Lubrication Journal, Vol. 15, No. 6" and “Additives For Petroleum Products", written by Toshio Sakurai and published by Saiwai Bookstore.
  • the lubricating oil compositions of the invention are utilizable as lubricating oils requiring oxidation stability including, for example, motorcar engine oils, engine oils for agricultural machines, diesel engine oils, diesel engine oils, industrial multipurpose lubricating oils, turbine oils, hydraulic oils, spindle oils, film forming. oils, refrigerator oils, gear oils, automatic transmission oils, cylinder oils dynamo oils, machine oils, cutting oils, and metal processing oils.
  • N-p-alkylphenyl-alpha-naphthylamine as the component (II) and the p,p′-dialkyldiphenylamine as the component (III) according to this invention indicated in the following Table 1, were added in the respective amounts shown in Table 1 to a refined mineral oil (kinematic viscosity 34.4 cSt at 40 o C) whose aromatic content was 7 wt.% to obtain a lubricating oil composition which was then subjected to the following evaluation test to find its service life and sludge formation under oxidizing conditions with the results being shown in Table 1 (Inventive Example).
  • a rotary bomb oxidation test was carried out at a test temperature of 150 o C and an oxygen pressure of 6.3 kg/cm2 at ambient temperature in the presence of a copper wire catalyst in accordance with JIS K 2514 3.3.
  • the service life under oxidizing conditions was evaluated in terms of a time during which the oxygen pressure decreased by 1.75 kg/cm2.
  • the oil compositions of the Example and Comparative Examples were tested for service life at an oil temperature of 80 o C and an operating pressure of 7.5 kg f/cm2.
  • the service life of each oil composition was determined in terms of time which elapsed from the start of the test until one of the following points (when the oil composition properties changed) was reached:
  • the lubricating oil composition of the inventive Example has excellent properties in exhibiting a synergistically extended service life without sludge formation as compared with those (Comparative Examples 1 - 3) wherein the component (II), the component (III) and the other compound were respectively used alone as additive.
  • the oil composition of Comparative Example 4 wherein one of the compounds added had an alkyl group outside of the range prescribed in the present invention, exhibited the same service life as that obtained in the inventive Example, but it formed sludges in a large amount; thus, the composition of Comparative Example 4 showed very inferior performance to the composition of the inventive Example.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP90309748A 1989-09-08 1990-09-06 Schmierölzusammensetzungen Expired - Lifetime EP0416914B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP231426/89 1989-09-08
JP1231426A JP2587296B2 (ja) 1989-09-08 1989-09-08 潤滑油組成物

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EP0416914A1 true EP0416914A1 (de) 1991-03-13
EP0416914B1 EP0416914B1 (de) 1993-07-28

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JP (1) JP2587296B2 (de)
KR (1) KR930011077B1 (de)
DE (1) DE69002426T2 (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995016765A2 (en) * 1993-12-15 1995-06-22 The B.F. Goodrich Company Synthetic ester lubricant stabilizer composition
EP0716141A3 (de) * 1994-12-07 1996-07-24 Nippon Oil Co Ltd
WO2008154334A1 (en) 2007-06-08 2008-12-18 Infineum International Limited Additives and lubricating oil compositions containing same
US8318645B2 (en) 2005-12-09 2012-11-27 Idemitsu Kosan Co., Ltd. Lubricant composition

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07188688A (ja) * 1993-12-27 1995-07-25 Nippon Oil Co Ltd アルミニウム塑性加工用潤滑油組成物
MY145889A (en) * 2004-07-08 2012-05-15 Shell Int Research Lubricating oil composition
KR20080056019A (ko) * 2005-10-17 2008-06-19 쉘 인터내셔날 리써취 마트샤피지 비.브이. 윤활유 조성물
JP2011051951A (ja) * 2009-09-03 2011-03-17 Jx Nippon Oil & Energy Corp ヒドリンダンの製造方法及び溶剤

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Publication number Priority date Publication date Assignee Title
US4096078A (en) * 1977-06-28 1978-06-20 Texaco Inc. Synthetic aircraft turbine oil
EP0097118A2 (de) * 1982-06-10 1983-12-28 Ciba-Geigy Ag Flüssige Antioxidantien für Schmierstoffe und Elastomere
EP0232154A2 (de) * 1986-02-04 1987-08-12 Nippon Oil Co. Ltd. Schmierölzusammensetzungen

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Publication number Priority date Publication date Assignee Title
JP2510088B2 (ja) * 1986-06-05 1996-06-26 日本石油株式会社 潤滑油組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4096078A (en) * 1977-06-28 1978-06-20 Texaco Inc. Synthetic aircraft turbine oil
EP0097118A2 (de) * 1982-06-10 1983-12-28 Ciba-Geigy Ag Flüssige Antioxidantien für Schmierstoffe und Elastomere
EP0232154A2 (de) * 1986-02-04 1987-08-12 Nippon Oil Co. Ltd. Schmierölzusammensetzungen

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995016765A2 (en) * 1993-12-15 1995-06-22 The B.F. Goodrich Company Synthetic ester lubricant stabilizer composition
WO1995016765A3 (en) * 1993-12-15 1995-07-27 Goodrich Co B F Synthetic ester lubricant stabilizer composition
EP0716141A3 (de) * 1994-12-07 1996-07-24 Nippon Oil Co Ltd
US5658866A (en) * 1994-12-07 1997-08-19 Nippon Oil Co., Ltd. Lubricating oil compositions
US8318645B2 (en) 2005-12-09 2012-11-27 Idemitsu Kosan Co., Ltd. Lubricant composition
WO2008154334A1 (en) 2007-06-08 2008-12-18 Infineum International Limited Additives and lubricating oil compositions containing same
US20100173811A1 (en) * 2007-06-08 2010-07-08 Stephen Arrowsmith Additives and lubricating oil compositions containing same
US8999903B2 (en) 2007-06-08 2015-04-07 Infineum International Limited Additives and lubricating oil compositions containing same

Also Published As

Publication number Publication date
EP0416914B1 (de) 1993-07-28
KR930011077B1 (ko) 1993-11-20
JPH0395297A (ja) 1991-04-19
JP2587296B2 (ja) 1997-03-05
DE69002426D1 (de) 1993-09-02
DE69002426T2 (de) 1994-03-24
KR910021468A (ko) 1991-12-20

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