EP0406826B1 - Schmierstoffzusammensetzung - Google Patents

Schmierstoffzusammensetzung Download PDF

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Publication number
EP0406826B1
EP0406826B1 EP90112762A EP90112762A EP0406826B1 EP 0406826 B1 EP0406826 B1 EP 0406826B1 EP 90112762 A EP90112762 A EP 90112762A EP 90112762 A EP90112762 A EP 90112762A EP 0406826 B1 EP0406826 B1 EP 0406826B1
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EP
European Patent Office
Prior art keywords
formula
hydrogen
group
c18alkyl
phenyl
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 - Lifetime
Application number
EP90112762A
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German (de)
English (en)
French (fr)
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EP0406826A1 (de
Inventor
Samuel Dr. Evans
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.)
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
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Definitions

  • the present invention relates to lubricant compositions that are stabilized against oxidative degradation. Stabilization is achieved by adding at least two specific additives.
  • Organic antioxidants for lubricants are primarily organic sulfur and phosphorus compounds, but also aromatic amines and phenols, especially sterically hindered phenols (see, for example, Ullmanns Encyklopadie der Technische Chemie, 4th edition, Verlag Chemie, Volume 20 (1981); page 541- 43).
  • Sterically hindered amines have also been proposed as stabilizers for lubricating oils, e.g. in US-A-4 069 199 or JP-A-85/28496.
  • EP-A-356 677 proposes mixtures of aromatic amines and sterically hindered amines as antioxidants for lubricants, it also being possible to add phenolic antioxidants to these mixtures.
  • US-A-4 836 943 describes mixtures of antioxidants containing hindered phenols and pipecoline derivatives.
  • the weight ratio of (B) to (C) is preferably 1: 1 to 1: 100, in particular 1: 3 to 1:20.
  • the sum of (B) and (C) is preferably 0.05 to 5% by weight, in particular 0.1 to 3% by weight, of (A).
  • a and B as C1-C24 alkyl can be linear or branched alkyl, e.g. Methyl, ethyl, i-propyl, t-butyl, s-butyl, s-pentyl, t-pentyl, n-hexyl, i-hexyl, t-hexyl, i-heptyl, n-octyl, t-octyl, s- Decyl, s-dodecyl, n-dodecyl, s-tetradecyl, n-hexadecyl, n-octadecyl, s-octadecyl or n-eikosyl.
  • a and B as cycloalkyl can e.g. Cyclopentyl, cyclohexyl or cyclooctyl, especially cyclohexyl.
  • a and B as phenylalkyl can e.g. Be benzyl, phenylethyl, phenylpropyl or ⁇ , ⁇ -dimethylbenzyl.
  • R5 and R6 as C1-C12 alkyl can be, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl or dodecyl.
  • R1, R2, R3 and R8 as C1-C18 alkyl can also be, for example, tetradecyl, hexadecyl or octadecyl.
  • R4 as C1-C24 alkyl can also be, for example, eikosyl or tetraeikosyl.
  • the index a is preferably 0, 1 or 2, in particular 0 or 1; b is preferably 0, 1 or 2, in particular 1 or 2; q is preferably 1 or 2, in particular 1.
  • Component (A) is a mineral or synthetic base oil, as is common for the preparation of lubricants.
  • Synthetic oils can e.g. Esters of polycarboxylic acids or of polyols, they can be aliphatic polyesters or poly- ⁇ -olefins, silicones, phosphoric acid esters or polyalkylene glycols.
  • the lubricant can also be a grease based on an oil and a thickener. Such lubricants are e.g. described in D. Klamann "Lubricants and related products", Verlag Chemie, Weinheim 1982.
  • Component (B) is a compound which contains at least one group of the formula II where R is hydrogen or methyl.
  • R is preferably hydrogen.
  • These are derivatives of polyalkylpiperidines, in particular 2,2,6,6-tetramethylpiperidine. These compounds preferably bear one or two polar substituents or a polar spiro ring system in the 4-position of the piperidine ring. These compounds can be low molecular weight or oligomeric or polymeric compounds.
  • n is a number from 1 to 4, preferably 1 or 2
  • R is hydrogen or methyl
  • R11 is hydrogen, oxyl, hydroxyl, C1-C12-alkyl, C3-C8 alkenyl, C3-C8-alkynyl, C7-C12-aralkyl , C1-C18 alkoxy, C5-C8-cycloalkoxy, C7-C9-phenylalkoxy, C1-C8-alkanoyl, C3-C5-alkenoyl, C1-C18-alkanoyloxy, benzyloxy, glycidyl or a group -CH2CH (OH) -Z , wherein Z is hydrogen, methyl or phenyl, where R11 is preferably H, C1-C4-alkyl, allyl, benzyl, acetyl or acryloyl and R12, when n is 1, is hydrogen, C
  • substituents are C1-C12-alkyl, they represent e.g. Methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, n-undecyl or n- Dodecyl.
  • R11 or R12 can e.g. represent the groups listed above and, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl.
  • R11 is C3-C8-alkenyl, it can e.g. 1-propenyl, allyl, methallyl, 2-butenyl, 2-pentenyl, 2-hexenyl, 2-octenyl, 4-tert. Act butyl-2-butenyl.
  • R11 is preferably as C3-C8 alkynyl propargyl.
  • R11 is especially phenethyl and especially benzyl.
  • R11 is as C1-C8 alkanoyl, for example formyl, propionyl, butyryl, octanoyl, but preferably acetyl and as C3-C5-alkenoyl in particular acryloyl.
  • R12 is a monovalent radical of a carboxylic acid, it is, for example, acetic, caproic, stearic, acrylic, methacrylic, benzoic or ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) - propionic acid residue.
  • R 12 is a divalent radical of a dicarboxylic acid, it represents, for example, malonic, succinic, glutaric, adipic, suberic, sebacic, maleic, itaconic, phthalic, dibutylmalonic, dibenzylmalonic, butyl (3 , 5-di-tert-butyl-4-hydroxybenzyl) -malonic acid or bicycloheptenedicarboxylic acid residue.
  • R 12 represents a trivalent carboxylic acid residue, it means, for example, a trimellitic acid, citric acid or nitrilotriacetic acid residue.
  • R 12 represents a tetravalent radical of a tetracarboxylic acid, it means e.g. the tetravalent residue of butane-1,2,3,4-tetracarboxylic acid or of pyromellitic acid.
  • R12 is a divalent radical of a dicarbamic acid, it represents, for example, a hexamethylene dicarbamic acid or a 2,4-tolylene dicarbamic acid radical.
  • Preferred compounds of the formula III are those in which R is hydrogen, R11 is hydrogen or methyl, n is 1 and R12 is C1-C18 alkyl or n is 2 and R12 is the diacyl radical of an aliphatic dicarboxylic acid having 4-12 C atoms.
  • R13 is hydrogen, C1-C12-alkyl, C2-C5-hydroxyalkyl, C5-C7-cycloalkyl, C7-C8-aralkyl, C2-C18 -Alkanoyl, C3-C5-alkenoyl, benzoyl or a group of the formula is and R14 when n is 1, hydrogen, C1-C18-alkyl, C3-C8-alkenyl, C5-C7-cycloalkyl, C1-C4-alkyl, glycidyl substituted with a hydroxy, cyano, alkoxycarbonyl or carbamide group, one Group of the formula -CH2-CH (OH) -Z or the formula -CONH-Z, wherein Z is hydrogen, methyl or phenyl; when n is 2, C2-C12 alkylene, C6-C12
  • any substituents are C5-C7-cycloalkyl, they represent in particular cyclohexyl.
  • R13 is especially phenylethyl or especially benzyl.
  • R13 is in particular 2-hydroxyethyl or 2-hydroxypropyl.
  • R13 is as C2-C18 alkanoyl, for example propionyl, butyryl, octanoyl, dodecanoyl, hexadecanoyl, octadecanoyl, but preferably acetyl and as C3-C5-alkenoyl, in particular acryloyl.
  • R14 is C2-C8 alkenyl, then it is e.g. allyl, methallyl, 2-butenyl, 2-pentenyl, 2-hexenyl or 2-octenyl.
  • R14 as a C1-C4-alkyl substituted with a hydroxy, cyano, alkoxycarbonyl or carbamide group can be, for example, 2-hydroxyethyl, 2-hydroxypropyl, 2-cyanoethyl, methoxycarbonylmethyl, 2-ethoxycarbonylethyl, 2-aminocarbonylpropyl or 2- (dimethylaminocarbonyl) - be ethyl.
  • substituents are C2-C12 alkylene, they are e.g. around ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
  • substituents are C6-C15 arylene, they represent e.g. o-, m- or p-phenylene, 1,4-naphthylene or 4,4'-diphenylene.
  • D is especially cyclohexylene.
  • n is the number 1 or 2
  • R and R11 have the meaning given under a) and R15, if n is 1, C2-C8-alkylene or hydroxyalkylene or C4-C22-acyloxyalkylene, if n is 2, the group ( -CH2) 2C means (CH2-) 2.
  • R15 means C2-C8-alkylene or hydroxyalkylene, it represents, for example, ethylene, 1-methyl-ethylene, propylene, 2-ethyl-propylene or 2-ethyl-2-hydroxymethylpropylene.
  • R15 means e.g. 2-ethyl-2-acetoxymethylpropylene.
  • R16 is hydrogen, C1-C12-alkyl, allyl, benzyl, glycidyl or C2-C6-alkoxyalkyl and R17, if n is 1, is hydrogen , C1-C12-alkyl, C3-C5-alkenyl, C7-C9-aralkyl, C5-C7 cycloalkyl, C2-C4-hydroxyalkyl, C2-C6-alkoxyalkyl, C6-C10-aryl, glycidyl or a group of the formula - ( CH2) p -COO-Q or of the formula - (CH2) p -O-CO-Q, where p is 1 or 2 and Q is C1-C4 alkyl or phenyl, if n is 2, C2-C12 alkylene, C4- C
  • substituents are C1-C12-alkyl, they represent e.g. Methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, n-undecyl or n- Dodecyl.
  • C1-C18 alkyl can e.g. represent the groups listed above and, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl.
  • substituents are C2-C6-alkoxyalkyl, they represent e.g. Methoxymethyl, ethoxymethyl, propoxymethyl, tert-butoxymethyl, ethoxyethyl, ethoxypropyl, n-butoxyethyl, tert-butoxyethyl, isopropoxyethyl or propoxypropyl.
  • R17 represents C3-C5-alkenyl, it means for example 1-propenyl, allyl, methallyl, 2-butenyl or 2-pentenyl.
  • T1 and T2 are especially phenethyl or especially benzyl. If T1 and T2 form a cycloalkane ring together with the C atom, this can e.g. be a cyclopentane, cyclohexane, cyclooctane or cyclododecane ring.
  • R17 is C2-C4-hydroxyalkyl, it is e.g. 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.
  • R17, T1 and T2 mean in particular phenyl, ⁇ - or ⁇ -naphthyl, which are optionally substituted by halogen or C1-C4-alkyl.
  • R17 is C2-C12 alkylene, it is e.g. around ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
  • R17 means in particular 2-butenylene, 2-pentenylene or 3-hexenylene.
  • R17 is C6-C12 arylene, it represents, for example, o-, m- or p-phenylene, 1,4-naphthylene or 4,4'-diphenylene.
  • Z 'means C2-C12 alkanoyl, for example propionyl, butyryl, octanoyl, dodecanoyl, but preferably acetyl.
  • D as C2-C10 alkylene, C6-C15 arylene or C6-C12 cycloalkylene has the meaning given under b).
  • n is the number 1 or 2 and R18 is a group of the formula means in which R and R11 have the meaning given under a)
  • E is -O- or -NR21-
  • A is C2-C6-alkylene or - (CH2) 3-O- and x is the number 0 or 1
  • R19 is the same R18 or one of the groups -NR21R22, -OR23, -NHCH2OR23 or -N (CH2OR23) 2,
  • substituents are C1-C12-alkyl, they are, for example, methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethylhexyl, n-nonyl , n-decyl, n-undecyl or n-dodecyl.
  • substituents are C1-C4-hydroxyalkyl, they represent e.g. 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.
  • R21 and R22 together represent C4-C5-alkylene or -oxaalkylene, this means e.g. Tetramethylene, pentamethylene or 3-oxapentamethylene.
  • polyalkylpiperidine compounds of this class are the compounds of the following formulas:
  • oligomers or polymeric compounds whose recurring structural unit contains a 2,2,6,6-tetraalkylpiperidine radical of the formula (I), 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.
  • R is hydrogen or methyl and R 11 is hydrogen or methyl.
  • the polyalkylpiperidines are known compounds and are used as light stabilizers for organic materials. Some of them are commercially available.
  • Component (C) is a phenolic antioxidant.
  • Preferred (C) is a compound of formula I, wherein A is hydrogen, C1-C8-alkyl, cyclohexyl, phenyl or a group means B is C1-C8-alkyl, cyclohexyl or phenyl, X C1-C8-alkyl or one of the groups -C a H 2a -S-R2, -C b H 2b -COOR3, -CH2N (R10) (R11) or means R2 is C1-C12-alkyl, phenyl or a group - (CH2) c -COOR4, R3 C1-C18 alkyl or a group is wherein Q is C2-C6-alkylene, -CH2CH2SCH2CH2- or -CH2CH2 (OCH2CH2) d -, R4 is C1-C18 alkyl, R10 and R11 are independently C1-
  • a class which is particularly suitable as component (C) are the compounds of the formula I in which A and B independently of one another are C1-C4alkyl, X is a group -C a H 2a -S q -R2, a is 0 or 1, q is 1 or 2, R2 is C4-C18-alkyl, phenyl or -CH2-CO-OR und and R4 is C1-C18-alkyl, in particular the compounds of the formula I, in which A and B independently of one another are C1-C4-alkyl , X is -CH2-S-R2, R2 is C8-C12-alkyl or -CH2-CO-OR4 and R4 is C8-C18-alkyl.
  • Particularly preferred in this class are compounds of the formula I in which A and B are tert-butyl and X is -CH2SCH2COO (C8-C13-alkyl).
  • component (C) Another class particularly suitable as component (C) are the compounds of the formula I in which A and B independently of one another are C1-C4alkyl, X is a group -C b H 2b -CO-OR3, b is 1 or 2 and R3 is one of the groups or means especially the compounds of formula I, wherein X is a group - (CH2) 2-CO-OR3 and R3 is a group means.
  • component (C) Another class particularly suitable as component (C) are the methylene bisphenols of the formula or wherein A, B and X are independently C1-C4 alkyl.
  • Mixtures of polyphenols such as are obtained by reacting at least one dialkylated phenol of the formula, are also particularly suitable as component (C) with at least one monoalkylated phenol of the formula and formaldehyde or paraformaldehyde is obtained, where C, D and E independently of one another are C1-C4-alkyl.
  • the resulting mixtures mainly contain diphenols and triphenols.
  • Examples of compounds of the formula I are: Tridecyl 4- (4-hydroxy-3,5-di-tert-butylphenyl) -3-thiabutyrate 3-thia-1,5-pentadiol-di [3- (4-hydroxy-3,5-di-tert-butylphenyl)] propionate Di (3-thiapentadecyl) di (4-hydroxy-3,5-di-tert-butylphenyl) malonate Octadecyl 4- (4-hydroxy-3,5-di-tert-butylphenyl) -3-thiabutyrate 4- (2-thiapropyl) -2,6-di-tert-butylphenol Octadecyl 3- (4-hydroxy-3,5-di-tert-butylphenyl) propionate 3-thiapentadecyl-3- (4-hydroxy-3,5-di-tert-butylphenyl) propionate Di (4-hydroxy-3,
  • butylphenol 4,4'-methylene-bis [2-tert. butyl-4- (4-hydroxy-3,5-di-tert-butylbenzyl) phenol] 4-dimethylaminomethyl-2,6-di-tert. butylphenol 4-dibutylamino-methyl-2-methyl-6-tert. butylphenol N-Di (4-hydroxy-3,5-di-tert-butylbenzyl) octylamine
  • compositions are those in which (B) is a compound of formula IX or X, wherein n is 1 or 2, R11 is hydrogen or methyl and Y, when n is 1, means -O (C8-C15-alkyl), and when n is 2, a group -NH- (CH2) 6-NH- or Means -O-CO- (CH2) m -CO-O-, wherein m is 2-8, and (C) is a compound of formula I wherein A is hydrogen, C1-C4 alkyl or a group means B is C1-C4-alkyl, x C1-C4-alkyl or one of the groups -CH2-S-R2, -CH2CH2COOR3, -CH2N (R10) (R11) or means R2 is C1-C18 alkyl or - (CH2) 2-COOR4, R3 C1-C18 alkyl or means R4 is C1-C18 alkyl and R10 and R11 are
  • Components (B) and (C) can be added directly to the base oil or first (B) and (C) are dissolved in a small amount of base oil, optionally with heating, and the solution is mixed with the remaining amount of the oil.
  • a concentrated solution of (B) and (C) in a solvent can also be added to the oil.
  • the lubricant composition may additionally contain other additives such as e.g. Phosphorus III esters, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, surfactants and / or wear protection additives.
  • additives e.g. Phosphorus III esters, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, surfactants and / or wear protection additives.
  • Examples of phosphorus III esters are: Triphenyl phosphite, decyl diphenyl phosphite, phenyl didecyl phosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris- (2,4-di-tert.butylphenyl) phosphite, diisodhritol bisdi 4-di-tert.butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert.butylphenyl) -4,4'-biphenylene diphosphonite, bis- (2,6-di-tert .butyl-4-methyl
  • metal deactivators for example for copper
  • Triazoles Triazoles, benzotriazoles and their derivatives, tolutriazoles and their derivatives, 2-mercaptobenzthiazole, 2-mercaptobenztriazole, 2,5-dimercaptobenztriazole, 2,5-dimercaptobenzthiadiazole, 5,5'-methylenebisbenzotriazole, 4,5,6,7-tetrahydrobenztriazole, salicylides -propylenediamine, salicylaminoguanidine and its salts.
  • viscosity index improvers are: Polyacrylates, polymethacrylates, vinyl pyrrolidone / methacrylate copolymers, polyvinyl pyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers, polyethers.
  • pour point depressants are: Polymethacrylate, alkylated naphthalene derivatives.
  • dispersants / surfactants are: Polybutenylsuccinic acid amides or imides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.
  • wear protection additives are: Compounds containing sulfur and / or phosphorus and / or halogen, such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl di- and tri-sulfides, triphenyl phosphorothionates, diethanolaminomethyltolyltriazole, di (2-ethyltylylolyl) aminol.
  • sulfurized vegetable oils such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl di- and tri-sulfides, triphenyl phosphorothionates, diethanolaminomethyltolyltriazole, di (2-ethyltylylolyl) aminol.
  • the lubricant can also contain solid lubricants, e.g. Graphite or molybdenum sulfide.
  • the oxidation behavior of lubricating oils stabilized according to the invention is tested according to the TOST method (turbine oxidation stability test) in accordance with ASTM D-943.
  • a mineral oil Mobil STOCK 305
  • Reocor® 12 a corrosion inhibitor
  • the total amount of stabilizers is 0.25%, based on the oil.
  • the composition of the stabilizer mixture is varied. The results are shown in Table 1.
  • the total concentration is 0.25%, based on the oil.
  • the oxidation resistance of the oils stabilized according to the invention is measured in a differential scanning calorimeter.
  • a base oil with 0.025% iron (III) acetylacetonate (as an oxidation catalyst) and 0.55% of a stabilizer is mixed in an aluminum dish and isothermally heated to 160 ° C under 10 bar oxygen in the calorimeter.
  • the time until the start of the exothermic reaction T B (induction time) and the time until the end of the exothermic reaction T E are measured. The longer the induction time, the higher the resistance to oxidation.
  • the phenolic antioxidants P-1 and P-2 are used as stabilizers as well as: P-3: reaction product of 160 g of 2,6-di-tert. butylphenol, 40 g 2-tert. butylphenol, 5.8 g KOH, 50 ml ethanol and 24 g paraformaldehyde at 80 ° C, containing as main components
  • the sterically hindered amine is used
  • the oxidation resistance is tested as in Example 6 in a differential scanning calorimeter, with the difference that instead of oxygen under 8 bar of air, which is mixed with 380 ppm (NO) x , is measured and that the isothermal temperature is 170 ° C. . Only the beginning of the exotherm is measured.

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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)
  • Hydrogenated Pyridines (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP90112762A 1989-07-07 1990-07-04 Schmierstoffzusammensetzung Expired - Lifetime EP0406826B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH252889 1989-07-07
CH2528/89 1989-07-07

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EP0406826A1 EP0406826A1 (de) 1991-01-09
EP0406826B1 true EP0406826B1 (de) 1993-08-11

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JP (1) JP2943004B2 (xx)
KR (1) KR0151400B1 (xx)
CN (1) CN1028243C (xx)
BR (1) BR9003187A (xx)
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US5486316A (en) * 1987-06-01 1996-01-23 Henkel Corporation Aqueous lubricant and surface conditioner for formed metal surfaces
US5198130A (en) * 1991-01-08 1993-03-30 Ciba-Geigy Corporation Lubricant compositions
JP3401349B2 (ja) * 1994-12-07 2003-04-28 新日本石油株式会社 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
JP4946063B2 (ja) * 2006-01-12 2012-06-06 日本精工株式会社 グリース組成物及び転がり軸受
PL2049630T3 (pl) * 2006-07-31 2015-10-30 Basf Se Kompozycja smarowa
WO2014017182A1 (ja) 2012-07-27 2014-01-30 Ｊｘ日鉱日石エネルギー株式会社 潤滑油組成物および銅および鉛の溶出を抑制した摺動材料の潤滑方法
FR3020377B1 (fr) * 2014-04-25 2020-11-27 Total Marketing Services Composition lubrifiante comprenant un compose anti-cliquetis
WO2016156328A1 (en) * 2015-03-31 2016-10-06 Shell Internationale Research Maatschappij B.V. Use of a lubricating composition comprising a hindered amine light stabilizer for improved piston cleanliness in an internal combustion engine
CN110273159A (zh) * 2019-07-02 2019-09-24 宜兴市中大凯水处理有限公司 一种新型高温缓蚀剂及其制备方法

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US4069199A (en) * 1973-12-28 1978-01-17 Ciba-Geigy Corporation Metal salts of hindered piperidine carboxylic acids and stabilized compositions

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US3336226A (en) * 1965-12-28 1967-08-15 Chevron Res Phenolic pour point depressants
US3480635A (en) * 1966-09-28 1969-11-25 Universal Oil Prod Co N-piperidyl substituted phenylenediamines
DE3266599D1 (en) * 1981-02-19 1985-11-07 Ciba Geigy Ag Organic elastomers and mineral and synthetic lubricating oils containing phenolmercaptocarboxylic esters as stabilizers
US4362887A (en) * 1981-04-10 1982-12-07 The Goodyear Tire & Rubber Company Synergistic antioxidant mixtures
US4582943A (en) * 1983-12-23 1986-04-15 Ciba-Geigy Corporation Stabilization of polyalkylene glycols
US4607104A (en) * 1985-07-11 1986-08-19 Uniroyal Chemical Company, Inc. Process for the production of 2,2,6,6-tetraalkyl-4-piperidylamines
CA1248516A (en) * 1985-07-15 1989-01-10 Stephen C. Cohen Lubricating oil compositions containing novel combination of stabilizers
DE3671241D1 (de) * 1985-11-13 1990-06-21 Ciba Geigy Ag Substituierte phenole als stabilisatoren.
EP0273013B2 (de) * 1986-12-24 1996-07-24 Ciba-Geigy Ag Substituierte Phenole als Stabilisatoren
US4836943A (en) * 1987-07-15 1989-06-06 Texaco Inc. Anti-oxidant system
EP0346283B1 (de) * 1988-06-09 1992-07-29 Ciba-Geigy Ag Schmierölzusammensetzung
US5073278A (en) * 1988-07-18 1991-12-17 Ciba-Geigy Corporation Lubricant composition

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US4069199A (en) * 1973-12-28 1978-01-17 Ciba-Geigy Corporation Metal salts of hindered piperidine carboxylic acids and stabilized compositions

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CA2020558C (en) 2001-11-06
CA2020558A1 (en) 1991-01-08
EP0406826A1 (de) 1991-01-09
DE59002284D1 (de) 1993-09-16
JP2943004B2 (ja) 1999-08-30
KR910003079A (ko) 1991-02-26
KR0151400B1 (ko) 1998-10-01
ZA905305B (en) 1991-05-29
BR9003187A (pt) 1991-08-27
CN1048560A (zh) 1991-01-16
DD297443A5 (de) 1992-01-09
CN1028243C (zh) 1995-04-19
JPH0345696A (ja) 1991-02-27

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