EP0432089A1 - Compositions lubrifiantes - Google Patents

Compositions lubrifiantes Download PDF

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Publication number
EP0432089A1
EP0432089A1 EP90810831A EP90810831A EP0432089A1 EP 0432089 A1 EP0432089 A1 EP 0432089A1 EP 90810831 A EP90810831 A EP 90810831A EP 90810831 A EP90810831 A EP 90810831A EP 0432089 A1 EP0432089 A1 EP 0432089A1
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EP
European Patent Office
Prior art keywords
alkyl
tert
bis
phenyl
compounds
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
EP90810831A
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German (de)
English (en)
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EP0432089B1 (fr
Inventor
Rolf Dr. Schumacher
Horst Dr. Zinke
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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Publication of EP0432089A1 publication Critical patent/EP0432089A1/fr
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04Hydroxy compounds
    • C10M129/10Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04Hydroxy compounds
    • C10M129/10Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
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    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
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    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
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    • C10M135/20Thiols; Sulfides; Polysulfides
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    • C10M135/28Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/041Triaryl phosphates
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/02Groups 1 or 11

Definitions

  • Mineral lubricating oil mixtures and in particular steam turbine oils with improved stability are known for example from DE-AS 1 594 405.
  • Steam turbine oils are described which contain an aliphatic carboxylic acid having at least 12 carbon atoms, an alkylphenol, an aromatic amine and a dialkyldithiophosphate.
  • the alkali metal salts of dialkylthiophosphates are mentioned, preferred and only the zinc dialkyldithiophosphates have found their way into the practical examples.
  • R X , M ⁇ , X, X 1 , X 2 , a and b in compounds of the general formula I have the following meanings, for example.
  • R x represents C 7 -C 13 aralkyl which is interrupted in the alkyl radical by -0- or -S-, a typical example of this is a phenoxyethyl group.
  • compositions in which in the compounds of formula IX is sulfur furthermore those in which in the compounds of formula IX are sulfur and X 1 and X 2 are oxygen; or those in which in the compounds of the formula IX are sulfur, X 1 is oxygen and X 2 is sulfur.
  • R 1 and R 9 as cycloalkyl having 5 to 12 carbon atoms represent, for example, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl or cyclododecyl. Cyclohexyl is preferred.
  • R "or R 12 can represent, for example, the groups mentioned above and, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl.
  • R 12 represents a trivalent carboxylic acid residue, it means, for example, a trimellitic acid, citric acid or nitrilotriacetic acid residue.
  • Any C 2 -C 12 alkylene substituents are, for example, ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
  • R 15 is C 2 -C 8 -alkylene or -hydroxyalkylene, it is, for example, ethylene, 1-methyl-ethylene, propylene, 2-ethyl-propylene or 2-ethyl-2-hydroxymethylpropylene.
  • R 17 is C 2 -C 12 alkylene, it is, for example, ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
  • oligomers or polymeric compounds whose recurring structural unit contains a 2,2,6,6-tetraalkylpiperidine radical of the formula (VI), in particular polyesters, polyethers, polyamides, polyamines, polyurethanes, polyureas, polyaminotriazines, poly (meth) acrylates, poly ( meth) acrylamides and their copolymers which contain such radicals.
  • 2,2,6,6-polyalkylpiperidine light stabilizers of this class are the compounds of the following formulas, where m is a number from 2 to about 200. g) compounds of the formula XII wherein R and R "have the meaning given under a).
  • compositions containing compounds of the formula V in which R 4 has the meaning of hydrogen or alkyl having 1 to 4 C atoms and preferably the meaning of alkyl having 1 to 4 C atoms and in particular tert-butyl are particularly useful.
  • R " Cs-C 18 alkyl and in particular iC 8 H 17 or iC 13 H 27 .
  • Preferred alkyl groups for A are methyl, ethyl, propyl and butyl groups; methyl and tert-butyl are particularly preferred.
  • A is the radical -CqH 2 qN (R ') (R ")
  • typical examples are -CH 2 -N (C 1 -C 4 alkyl) 2 and especially -CH 2 -N (CH 3 ) 2 .
  • the molar ratio of diphenylamine to diisobutylene can vary over a wide range, but is preferably kept in the range from 1: 1.11 to 1: 2.5, particularly preferably 1: 1.3 to 1: 1.75, in order to reduce the cost of To reduce the starting material and to keep the addition time of diisobutylene as short as possible.
  • the compounds of the formula III are obtainable, for example, by reacting diphenylamine with sulfur (US 2,433,658).
  • the compounds of the cyclic sterically hindered amine series are obtainable by processes which are known per se and which can be found in the relevant literature.
  • compositions according to the present invention can contain A) a lubricant and, for example, 0.01 to 10% by weight, based on the composition, of a mixture of B), C) and D), as described above.
  • 0.1 to 5% by weight, based on the composition, of a mixture of B), C) and D) is present.
  • the mixture of B), C) and D) can contain, for example, 20 to 88% by weight of B), 10 to 60% by weight of C) and 2 to 20% by weight of D), the percentages are based on the mixture.
  • B) 30 to 80% by weight, C) 10 to 60% by weight and D) 4 to 15% by weight are preferably present in the mixture of B), C) and D).
  • This device is based on the following principle: A steel ball (100 Cr 6), on which a force F N acts, oscillates on a steel cylinder.
  • the ball is fixed in a holder and therefore carries out an oscillating sliding movement.
  • the horizontal and vertical force is determined by a piezoelectric force transducer.
  • the maximum Hertzian normal stress is 2740 N / mm 2
  • the maximum shear stress is 850 N / mm 2 .
  • Ball and cylinder are made from the same tool steel.
  • the process works according to the following principle:
  • the PDSC cell (thermal analysis system 1090 from DuPont) consists of a heating block made of silver. In this heating block a constantan plate is inserted, which contains the thermocouples (Chromel-Alumel). Sample pans and reference pans are placed on the slightly elevated thermocouples. The interior of the DSC cell is covered with a thin gold film (corrosion protection). The reference pan remains empty, three drops of the respective formulation are poured into the sample pan. The temperature difference between sample and reference pans is determined under isothermal conditions. The enthalpy change dH / dt is given in mW. All measurements are carried out in air containing 400 ppm NO x . The pressure is 8 bar.
  • Aral RL 136 a commercially available "black sludge reference oil", is used as the base oil. In order to increase the susceptibility to oxidation of the oil, 1% 1-decene is added to this oil.
  • the concentration of the added additives decreases continuously.
  • the heat flow dQ / dt increases.
  • the time that passes until this increase occurs is called the induction time (onset). Accordingly, long induction times indicate a high aging stability of the oils.
  • the formulations characterized by PDSC are from Table 2 evident.
  • Example 15 Thermal stabilization of a mineral oil.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP90810831A 1989-11-08 1990-10-30 Compositions lubrifiantes Expired - Lifetime EP0432089B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH401889 1989-11-08
CH4018/89 1989-11-08

Publications (2)

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EP0432089A1 true EP0432089A1 (fr) 1991-06-12
EP0432089B1 EP0432089B1 (fr) 1996-09-04

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Country Status (6)

Country Link
US (1) US5167844A (fr)
EP (1) EP0432089B1 (fr)
JP (1) JPH03168297A (fr)
CA (1) CA2029402A1 (fr)
DE (1) DE59010484D1 (fr)
ES (1) ES2091236T3 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2671354A1 (fr) * 1991-01-08 1992-07-10 Ciba Geigy Ag Compositions lubrifiantes renfermant une association de stabilisants.
EP0716141A3 (fr) * 1994-12-07 1996-07-24 Nippon Oil Co Ltd
EP0781834A3 (fr) * 1995-12-28 1997-08-20 Nippon Oil Co Ltd Composition d'huile lubrifiante
WO2009013275A1 (fr) * 2007-07-23 2009-01-29 Shell Internationale Research Maatschappij B.V. Composition lubrifiante destinée à être utilisée dans des moteurs diesel compatibles avec un biocarburant
CN114657545A (zh) * 2021-03-12 2022-06-24 塞尔纳新材料(武汉)有限公司 一种生态除鳞型快速沉降钝化液及其制备工艺

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DE4138481A1 (de) * 1991-11-22 1993-05-27 Kempten Elektroschmelz Gmbh Wiederaufarbeitung von gebrauchten verdampferschiffchen
JP2859077B2 (ja) * 1993-04-09 1999-02-17 出光興産株式会社 潤滑油組成物
JP3527555B2 (ja) * 1994-12-09 2004-05-17 出光興産株式会社 熱処理油組成物
JP3508785B2 (ja) * 1994-12-13 2004-03-22 出光興産株式会社 ギヤ用潤滑油組成物
JP3527556B2 (ja) * 1994-12-14 2004-05-17 出光興産株式会社 内燃機関用潤滑油組成物
GB0011189D0 (en) * 2000-05-10 2000-06-28 Great Lakes Chemical Europ Anti-oxidant additives
BR0310057A (pt) 2002-05-17 2007-04-10 Othera Pharmaceuticals Inc melhoria do desenvolvimento de catarata e outras doenças oftálmicas
US6797677B2 (en) 2002-05-30 2004-09-28 Afton Chemical Corporation Antioxidant combination for oxidation and deposit control in lubricants containing molybdenum and alkylated phenothiazine
US6599865B1 (en) 2002-07-12 2003-07-29 Ethyl Corporation Effective antioxidant combination for oxidation and deposit control in crankcase lubricants
US7825134B2 (en) 2003-05-19 2010-11-02 Othera Holding, Inc. Amelioration of cataracts, macular degeneration and other ophthalmic diseases
US8466096B2 (en) * 2007-04-26 2013-06-18 Afton Chemical Corporation 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions
RU2493243C2 (ru) * 2009-02-02 2013-09-20 Ар.Ти. ВАНДЕРБИЛТ КОМПАНИ, ИНК. Беззольная смазывающая композиция
US8716359B2 (en) * 2010-03-18 2014-05-06 Vanderbilt Chemicals, Llc Polyurethane foam scorch inhibitor

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EP0059168A1 (fr) * 1981-02-19 1982-09-01 Ciba-Geigy Ag Elastomères organiques et huiles lubrifiantes minérales et synthétiques contenant des esters phénolmercaptocarboxyliques comme stabilisants
EP0267875A2 (fr) * 1986-11-11 1988-05-18 Ciba-Geigy Ag Composition lubrifiante pour haute température
EP0346283A2 (fr) * 1988-06-09 1989-12-13 Ciba-Geigy Ag Composition lubrifiante
EP0356677A1 (fr) * 1988-07-18 1990-03-07 Ciba-Geigy Ag Composition lubrifiante

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DE2364121A1 (de) * 1972-12-27 1974-07-11 Ciba Geigy Ag Verfahren zur herstellung von hydroxyalkylphenylderivaten
EP0059168A1 (fr) * 1981-02-19 1982-09-01 Ciba-Geigy Ag Elastomères organiques et huiles lubrifiantes minérales et synthétiques contenant des esters phénolmercaptocarboxyliques comme stabilisants
EP0267875A2 (fr) * 1986-11-11 1988-05-18 Ciba-Geigy Ag Composition lubrifiante pour haute température
EP0346283A2 (fr) * 1988-06-09 1989-12-13 Ciba-Geigy Ag Composition lubrifiante
EP0356677A1 (fr) * 1988-07-18 1990-03-07 Ciba-Geigy Ag Composition lubrifiante

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2671354A1 (fr) * 1991-01-08 1992-07-10 Ciba Geigy Ag Compositions lubrifiantes renfermant une association de stabilisants.
BE1004925A5 (fr) * 1991-01-08 1993-02-23 Ciba Geigy Ag Compositions lubrifiantes renfermant une association de stabilisants.
EP0716141A3 (fr) * 1994-12-07 1996-07-24 Nippon Oil Co Ltd
EP0781834A3 (fr) * 1995-12-28 1997-08-20 Nippon Oil Co Ltd Composition d'huile lubrifiante
US5912212A (en) * 1995-12-28 1999-06-15 Nippon Oil Co., Ltd. Lubricating oil composition
WO2009013275A1 (fr) * 2007-07-23 2009-01-29 Shell Internationale Research Maatschappij B.V. Composition lubrifiante destinée à être utilisée dans des moteurs diesel compatibles avec un biocarburant
CN114657545A (zh) * 2021-03-12 2022-06-24 塞尔纳新材料(武汉)有限公司 一种生态除鳞型快速沉降钝化液及其制备工艺
CN114657545B (zh) * 2021-03-12 2023-11-24 塞尔纳新材料(武汉)有限公司 一种生态除鳞型快速沉降钝化液及其制备工艺

Also Published As

Publication number Publication date
EP0432089B1 (fr) 1996-09-04
ES2091236T3 (es) 1996-11-01
US5167844A (en) 1992-12-01
CA2029402A1 (fr) 1991-05-09
DE59010484D1 (de) 1996-10-10
JPH03168297A (ja) 1991-07-22

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