US3652411A - Polyglycol base lubricant - Google Patents

Polyglycol base lubricant Download PDF

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Publication number
US3652411A
US3652411A US882268A US3652411DA US3652411A US 3652411 A US3652411 A US 3652411A US 882268 A US882268 A US 882268A US 3652411D A US3652411D A US 3652411DA US 3652411 A US3652411 A US 3652411A
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United States
Prior art keywords
lubricant
alkyl
polyglycol
polyglycol base
amine
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US882268A
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English (en)
Inventor
Axel Klaus Commichau
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ExxonMobil Oil Corp
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Mobil Oil Corp
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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
    • 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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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/24—Aldehydes; Ketones
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
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    • 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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    • C10M133/38—Heterocyclic nitrogen compounds
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
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    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/027—Neutral salts thereof
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    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
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    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2215/26—Amines
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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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
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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
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • C—CHEMISTRY; METALLURGY
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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
    • C10M2223/04—Phosphate esters
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • 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
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties

Definitions

  • This invention relates to improved lubricant compositions, and in one of its aspects, relates to polyglycol base lubricant compositions having improved oxidation and heat stability under sustained periods of operation. More particularly, in this aspect, the invention relates to polyglycol base lubricant compositions which effectively meet modern requirements in respect of oxidation stability at relatively high temperature operating conditions, affording good loading capacity and rust protection over long periods of time.
  • polyglycol base lubricants have been suggested by the prior art. It has been found, however, that these lubricants have not always met the high demands made by modern industrial plant operations. Thus, these polyglycol lubricants have not succeeded in affording protection as lubricants in instances where oxidative stability, affording adequate rust protection, under sustained operation at relatively high temperatures is to be maintained. Hence, the ability to provide an effective polyglycol base lubricant, avoiding the aforementioned disadvantages, is highly desirable.
  • polyglycol base lubricants can be provided possessing improved oxidative stability under conditions of operation, containing, in minor proportion, as a stabilizer, a mixture comprising:
  • R,, R and R are alkyl, aryl, alkaryl, alkoxyalkyl or halogen-alkyl groups
  • g. at least one compound of the group consisting of aliphatically and aromatically substituted organic phosphites.
  • substituted amine (a) may comprise an aliphatically or aromatically substituted amine, or mixtures of such amines. Exemplary thereof are: diphenyl amine, dinaphthyl amine, phenyl beta naphthyl amine, phenyl alpha naphthyl amine, naphthyl amine, phenothiazine, paraphenylene diamine and their alkyl and/or aryl substitution products, and polytrimethyl dihydroquinoline.
  • these substituted amines can be represented by the formula:
  • R, and/or R are alkyl, cycloalkyl, phenyl, naphthyl, alkyl phenyl, alkyl naphthyl or alkyl aminophenyl and R is hydrogen, alkyl or alkoxyalkyl.
  • aliphatically substituted phenol examples include 4- tertiarybutyl catechol, 2,4-ditertiarybutyl paracresol, 2,6- ditertiarybutyl-4-methyl phenol, 4,4'-methylene-bis-(2,6- ditertiarybutyl phenol) and alkylated bis phenols.
  • these substituted phenols can be represented by the formula:
  • R, R R and/or R represent hydrogen, alkyl groups and/or hydroxy groups.
  • Component (e) as hereinbefore indicted is exemplified by benzotriazole, itself, or alkyl derivatives of benzotriazole.
  • Exemplary of the reaction product (f) of an organic acid and a substituted amine are: amine salts formed by neutralization of an organic acid such as butyric acid, benzoic acid, sulfamidoacetic acid, heptane carboxylic acid, cyclohexane sulfonic acid with a substituted amine such as butyl amine, cyclohexyl amine, octyl amine, monoethanol amine, diethanolamine, dicyclohexyl amine, morpholine, piperidine and octyl ammonium caprylate.
  • an organic acid such as butyric acid, benzoic acid, sulfamidoacetic acid, heptane carboxylic acid, cyclohexane sulfonic acid with a substituted amine such as butyl amine, cyclohexyl amine, octyl amine, monoethanol amine, diethanolamine, dicyclohex
  • the amine salt (f) can be formed by the neutralization of an organic acid R,COOI-I or R,SO H with an amine NI-IR R with R,, R and/or R representing hydrogen, alkyl, cycloalkyl, aryl and/or alkyl aryl and R, in addition representing alkyl sulfamidomethyl and R, and R also representing hydroxyalkyl or part of an alicyclic or heterocyclic saturated or unsaturated ring.
  • organic phosphite (g) are dialkyl or diaryl phosphites, including, di-n-octyl phosphite and dinonyl phenyl phosphite.
  • Representative thereof is an additive of the formula (R,O)(R O)POH, in which R, and/or R represent hydrogen, alkyl, cycloalkyl, aryl and/or alkyl aryl.
  • the aforementioned components (a) through (g) are employed in minor proportion with respect to the total weight of the lubricant composition, and are preferably employed in an amount from about 0.001 to about 5 percent by weight.
  • the additive mixture preferably is added to the polyglycol base lubricant by intimate admixture at a temperature between about 40 C. and about C.
  • Suitable initial products for the aforementioned addition include, for example, water, the univalent alcohols such as methanol, ethanol, propanol, butanol, 2-ethyl hexanol, isononanol, the bivalent alcohols such as ethylene glycol, propylene glycol, neopentyl glycol, cyclohexylene glycol, the trivalent alcohols such as glycerine, trimethylol ethane, trimethylol propane and, as examples, the alcohols with higher valence such as pentaerythritol, dipentaerythritol and sorbitol.
  • the univalent alcohols such as methanol, ethanol, propanol, butanol, 2-ethyl hexanol, isononanol
  • the bivalent alcohols such as ethylene glycol, propylene glycol, neopentyl glycol, cyclohexylene glycol
  • alkylene oxides added to hydroxyl groups of these compounds are ethylene oxide, propylene oxide, butylene oxide, cyclohexene oxide and decene oxide, it being possible for one or more of these oxiranes to be present as units in the end product.
  • Substitution of hydrogen atoms of the hydroxyl groups by etherization can be carried out by methyl, ethyl, butyl or cyclohexyl groups, for example; the same applies to esterization of hydrogen atoms on the hydroxyl groups to, for example,acety1,propiony1or butyryl groups.
  • Polyglycol Base Oil A polyglycol base oil was prepared by the addition reaction of propylene oxide to trimethylol propane, to produce a corresponding reaction product containing components having an average molecular weight of up to 3,000.
  • Polyglycol base lubricant A polyglycol base lubricant was prepared employing the above-described polyglycol base oil, in which this polyglycol base lubricant had the following composition:
  • Example 1 The above-described polyglycol base lubricant was subjected to a heat and oxidation test, as were also the aforementioned polyglycol base oil and an additional oil, which differed from the polyglycol base lubricant only in that they did not contain the phenyl-a-naphthyl amine (3 percent) (a). 25 ml. of the respective lubricants were individually placed in a glass tube and were maintained at a temperature of 347 F. (175 C.). liters of air were blown through the individual samples hourly in the presence of lead, aluminum, copper and iron catalysts. Oxidation or decomposition of the respective lubricants was indicated by increasing substance loss of the sample and the time was noted which elapsed before the sample showed no significant evaporation loss.
  • Example 2 The aforementioned polyglycol base lubricant was maintained in a glass tube with a bronze strip at 338 F. (170 C.) for a period of 10 days. At the end of this time 10 liters of air per hour were blown through the oil for a period of 47 hours. The same procedure was conducted with another oil which differed from the aforementioned polyglycol base lubricant only in that it did not contain the aforementioned phenol derivative (b), but in which the phenyl-a-naphthyl amine content, component (a), amounted to 5 percent. Following the above-described test, there were no apparent signs of sludge of precipitation on the bronze in the case of the polyglycol base lubricant. It was noted, however, that there was a brown precipitation in the case of the comparison sample. Surprisingly, it was noted that the component (b) did have such ef fect.
  • Example 3 Experimentation was conducted in accordance with German Industrial Standard DIN 51 354 gear test.
  • This test refers to the mechanical testing of gear oils in a gear rig by the F26 method which is described in the Journal of the Institute of Petroleum," Vol.52, No. 507, pp. 98-107 Mar. 1966, The object of the test is the prior examination and checking of gear oils by establishing their ultimate load-carrying capacity and the weight change on the teeth surfaces.
  • selected gear wheels are run using the splash lubrication method in the gear oil to be tested at a constant speed and fixed initial oil temperature. The load on the teeth surfaces is gradually increased. After every change in the load, the weight changes on the tested wheels are measured by weighing, and a record is made ofthe changes in the teeth surfaces (surface damage).
  • the polyglycol base lubricant and a comparison oil were tested.
  • the comparison oil differed from the polyglycol base lubricant only in that it did not contain the phosphorus component (c).
  • the results of the test revealed that the polyglycol base lubricant successfully met all of the requirements of the test in all of a series of 12 stages, while the comparison oil failed to do so in the ninth stage.
  • Example 4 The amount of corrosion protection afforded by two lubricating oils was determined in accordance with Standard ASTM Specification No. D 665. Different results were obtained with respect to the above-described polyglycol base lubricant and another oil, which differed from the former only in that it did not contain the amine salt component (g). The test objects in the polyglycol base lubricant oil, prepared in accordance with the present invention, were found to be entirely free from corrosion, while those in the comparison oil were found to be severely corroded.
  • Example 5 Examination of the catalysts employed in accordance with the test procedure described in Example 1 above, clearly revealed the metal protecting qualities of components (e) and (f) of the polyglycol base lubricant oil prepared in accordance with the present invention.
  • the polyglycol base lubricant it was found that the lead and copper catalyst exhibit no signs of wear after an operating time of 60 hours.
  • employing another oil, differing from the polyglycol base lubricant only in that it did not contain components (e) and (f) it was found that there was pitting on the lead catalyst and coating and discoloration on the copper catalyst under the same conditions.
  • Example 6 In accordance with the heat and oxidation test described in Example 1 above, the following polyglycol oils were subjected to aging at a temperature of 347 F. C.):
  • R R R and/or R represent hydrogen, alkyl groups 1.
  • a polyglycol base lubricant in major proportion containand/or hydroxy groups, ing a minor stabilizing proportion of a mixture comprising: e. at least one compound of the group consisting of a. a substituted amine represented by the formula: benzotriazole and its alkyl derivatives,
  • each of (a) through (g) is present in an amount of from about 0.001 to hydrogen, alkyl or alkoxyalkyl,
  • R 5 A lubricant as defined in claim 1 wherein (c) comprises & R3 diphenyl cresyl phosphate.
  • Rd 4 6.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
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US882268A 1969-12-04 1969-12-04 Polyglycol base lubricant Expired - Lifetime US3652411A (en)

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US3888776A (en) * 1973-02-12 1975-06-10 Ore Lube Corp Two-cycle engine oil
US4248726A (en) * 1977-05-13 1981-02-03 Nippon Oil Co., Ltd. High-viscosity refrigerator oil compositions
US4267064A (en) * 1978-10-25 1981-05-12 Nippon Oil Company, Ltd. Refrigeration lubricating oil compositions
US4283296A (en) * 1978-08-21 1981-08-11 Texaco Inc. Amine salt of N-triazolyl-hydrocarbyl succinamic acid and lubricating oil composition containing same
US4582943A (en) * 1983-12-23 1986-04-15 Ciba-Geigy Corporation Stabilization of polyalkylene glycols
US4652385A (en) * 1985-07-15 1987-03-24 Petro-Canada Inc. Lubricating oil compositions containing novel combination of stabilizers
US5124057A (en) * 1990-09-14 1992-06-23 Petro-Canada Inc. Synergistic antioxidant system for severely hydrocracked lubricating oils
US5279752A (en) * 1989-02-22 1994-01-18 Nippon Oil Co., Ltd. Composition for lubricating oil
US5328619A (en) * 1991-06-21 1994-07-12 Ethyl Petroleum Additives, Inc. Oil additive concentrates and lubricants of enhanced performance capabilities
US5342531A (en) * 1990-06-08 1994-08-30 Ethyl Petroleum Additives Limited Polyalkylene glycol lubricant compositions
US5560854A (en) * 1992-09-18 1996-10-01 Nissan Motor Co., Ltd. Working fluid composition for HFC refrigerant compressor containing benzotriazole derivatives, and a process for improving lubrication in a compressor
USH1652H (en) * 1992-08-20 1997-06-03 Shell Oil Company Stabilized polymer compositions comprising one or more lubricating additives
US5739167A (en) * 1992-06-03 1998-04-14 Novartis Corporation Desferrioxamine-B salts and their use as orally effective iron chelators
US5902777A (en) * 1995-10-19 1999-05-11 Idemitsu Kosan Co., Ltd. Hydraulic working oil composition
US20060069000A1 (en) * 2004-09-29 2006-03-30 Jun Dong Stabilized lubricant compositions
WO2009013275A1 (en) * 2007-07-23 2009-01-29 Shell Internationale Research Maatschappij B.V. Lubricating composition for use in diesel engines compatible with biofuel
US20100016196A1 (en) * 2008-06-27 2010-01-21 Gelbin Michael E Phosphite stabilizer for lubricating base stocks and thermoplastic polymers

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AU2584884A (en) * 1983-09-16 1985-03-21 Bankamerica Corp. Lubricant for use with alcoholic fuels
IN163879B (de) * 1984-09-17 1988-12-03 Bank Of America
JPS61156615U (de) * 1985-03-20 1986-09-29
DE68907763T2 (de) * 1988-04-06 1993-12-16 Nippon Oil Co Ltd Verwendung von Schmierölzusammensetzungen für Kühlapparate.
JP2588287B2 (ja) * 1989-02-22 1997-03-05 日本石油株式会社 冷凍機油組成物
FR2679246A1 (fr) * 1991-07-15 1993-01-22 Exxon France Composition d'huile et son utilisation comme isolant electrique.

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GB732086A (en) * 1952-11-29 1955-06-15 Standard Oil Dev Co Complex formal lubricating composition
DE1168729B (de) * 1956-03-19 1964-04-23 Bayer Ag Verwendung von í¬(CH)-O-Gruppen enthaltenden Polyaethern bzw. Polyaetherestern als Schmiermittel
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Cited By (22)

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US3888776A (en) * 1973-02-12 1975-06-10 Ore Lube Corp Two-cycle engine oil
US4248726A (en) * 1977-05-13 1981-02-03 Nippon Oil Co., Ltd. High-viscosity refrigerator oil compositions
US4283296A (en) * 1978-08-21 1981-08-11 Texaco Inc. Amine salt of N-triazolyl-hydrocarbyl succinamic acid and lubricating oil composition containing same
US4267064A (en) * 1978-10-25 1981-05-12 Nippon Oil Company, Ltd. Refrigeration lubricating oil compositions
US4582943A (en) * 1983-12-23 1986-04-15 Ciba-Geigy Corporation Stabilization of polyalkylene glycols
US4652385A (en) * 1985-07-15 1987-03-24 Petro-Canada Inc. Lubricating oil compositions containing novel combination of stabilizers
US5279752A (en) * 1989-02-22 1994-01-18 Nippon Oil Co., Ltd. Composition for lubricating oil
US5342531A (en) * 1990-06-08 1994-08-30 Ethyl Petroleum Additives Limited Polyalkylene glycol lubricant compositions
US5124057A (en) * 1990-09-14 1992-06-23 Petro-Canada Inc. Synergistic antioxidant system for severely hydrocracked lubricating oils
US5328619A (en) * 1991-06-21 1994-07-12 Ethyl Petroleum Additives, Inc. Oil additive concentrates and lubricants of enhanced performance capabilities
US5739167A (en) * 1992-06-03 1998-04-14 Novartis Corporation Desferrioxamine-B salts and their use as orally effective iron chelators
USH1652H (en) * 1992-08-20 1997-06-03 Shell Oil Company Stabilized polymer compositions comprising one or more lubricating additives
US5560854A (en) * 1992-09-18 1996-10-01 Nissan Motor Co., Ltd. Working fluid composition for HFC refrigerant compressor containing benzotriazole derivatives, and a process for improving lubrication in a compressor
US5902777A (en) * 1995-10-19 1999-05-11 Idemitsu Kosan Co., Ltd. Hydraulic working oil composition
US20060069000A1 (en) * 2004-09-29 2006-03-30 Jun Dong Stabilized lubricant compositions
US20060073992A1 (en) * 2004-09-29 2006-04-06 Jun Dong Stabilized lubricant compositions
US7799101B2 (en) 2004-09-29 2010-09-21 Chemtura Corporation Stabilized lubricant compositions
US7829511B2 (en) 2004-09-29 2010-11-09 Chemtura Corporation Stabilized lubricant compositions
WO2009013275A1 (en) * 2007-07-23 2009-01-29 Shell Internationale Research Maatschappij B.V. Lubricating composition for use in diesel engines compatible with biofuel
US20100269774A1 (en) * 2007-07-23 2010-10-28 Noriaki Shinoda Lubricating composition for use in diesel engines compatible with biofuel
US20100016196A1 (en) * 2008-06-27 2010-01-21 Gelbin Michael E Phosphite stabilizer for lubricating base stocks and thermoplastic polymers
US8049041B2 (en) 2008-06-27 2011-11-01 Chemtura Corporation Phosphite stabilizer for lubricating base stocks and thermoplastic polymers

Also Published As

Publication number Publication date
CA953280A (en) 1974-08-20
NL166059C (nl) 1981-06-15
DE2057196A1 (de) 1971-06-09
ZA705671B (en) 1972-03-29
AT303944B (de) 1972-12-11
DE2057196C2 (de) 1983-12-08
NL166059B (nl) 1981-01-15
JPS491339B1 (de) 1974-01-12
NL7017560A (de) 1971-06-08
GB1290560A (de) 1972-09-27
FR2068771A1 (de) 1971-09-03
FR2068771B1 (de) 1975-01-10

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