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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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  • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
  • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
  • C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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  • C10M2207/283—Esters of polyhydroxy compounds
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
  • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
  • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
  • C10M2215/222—Triazines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
  • C10M2215/226—Morpholines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/30—Heterocyclic compounds
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  • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
  • C10M2227/09—Complexes with metals
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/02—Groups 1 or 11
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  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/08—Resistance to extreme temperature
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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/12—Gas-turbines
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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/12—Gas-turbines
  • C10N2040/13—Aircraft turbines

Definitions

• This invention relates to a lubricant composition containing a superior antioxidant combination. More particularly, the present invention relates to an additive combinatrion for ester base lubricant compositions having excellent stabilizing eiiects at extremely high lubricating temperatures.
• ester compositions It is an object of the present invention to provide improved ester compositions. It is a particular object of the invention to provide ester compositions having reduced tendencies to form acidic oxidation products. It is a particular object of the invention to provide ester lubricants especially useful as gas turbine lubricants and hydraulic fluids.
• a superior lubricant composition comprising an estertype base fiuid and oxidation stabilizing amounts of both an amine of the group consisting of certain triazines and certain pyridylamines in combination with critically limited proportions of complexes of such classes of amines with copper salts of fatty acids.
• the optimum mol ratio of the combination is from 2 to 75 mols of total amine for each mol of copper.
• the copper complexes which are formed between the amine and the copper salt are believed to be of the square planar type.
• the precise structure of the complexes has not been absolutely determined. They appear to exist in a ratio of about 2 mols of the amine for each mol of the copper salt.
• Part of the unexpected character of the present invention lies in the fact that copper is known to be a serious accelerator of oxidation. Consequently the present invention is based upon the discovery that an optimum ratio exists wherein an excess of firee amine is present beyond the amount necessary for forming the complex for the copper salt and within which ratio a remarkable stabilization of the oxidation properties of the ester base lubricant is observed.
• the copper salts to be employed in the preparation of the subject complexes are preferably those with the copper in the second oxidative state (copper II), while the fatty acid radical may be derived from any fatty acid having from 2-24 carbon atoms. These include the usual acids such as acetic, propionic, butyric, hexoic, octanoic, :dodecanoic, cap-ric, caprylic, caproic, stearic, oleic, linoleic, etc. It is preferred that the acid be saturated and have from 2 to 12 carbon atoms per molecule.
• the amines which are utilized in their free form and also in complex with the copper salt are of two general categories. These may be referred to as pyridylamines and triazines.
• the pyridylamines are those having at least one pyridyl radical and preferably two and comprise unsubstituted pyridylamines as well as alkyl substituted, and those pyridylamines having assiibstituent groups amino radicals, aryl radicals, aminoaryls, aminoalkyls, and triazyl radicals.
• Table A which follows, lists typical pyridylamines coming within the scope of this invention.
• the triazines may be used as the sole amine in the composition or may be combined with the pyridylamines. Suitable types are those constituted by unsubstituted triamine, or more preferably the guanamines in addition to monoarninotriazines, alkyl triazines, aryltriazines or triazinylamine. Table 13 which follows lists typical species suitable for this purpose.
• the copper salt complexes of these amine types may be formed in situ or may be preformed before dispersal in the ester base lubricants.
• the complexes are immediately formed by combining solutions such as alcohol solutions of the amine and copper salt and evaporating to dryness. However, complexes appear to be just as efficiently" formed by combining the free amine and the copper salt in the ester lubricant.
• metal complex is an equilibrium reaction; therefore, an excess of free amine appears to serve two principal purposes. First, it minimizes the amount of free soluble copper ion which would act as a pro-oxidant and secondly it assures as large an amount of active inhibitor as possible by displacing the equilibrium toward the product, namely, the complex. If excessive amounts of the copper compound are present, then the pro-oxidant effect of copper becomes predominant and causes an acceleration rather than a retardation of oxidation. On the other hand, if excessive amounts of free amine are present (or not enough copper to form sufficient amounts of the complex, the active inhibitor) then the oxidation inhibition is minimized since the free amines do not appear to be very eifective inhibitors. Thus, it was found by means of comparative testing that the maximum oxidation inhibition was obtained when the mol ratio of total amine to copper was between about 2 and about 75, preferably be tween about and about 35.
• aliphatic esters which are used primarily for synthetic hydraulic fluids and gas turbine lubricants as well as for other associated purposes.
• the principal classes included within this broad class of aliphatic esters comprise esters formed between dicarboxylic acids and monohydric alcohols; esters formed between neopentyl glycols and monohydric-alcohols; esters of pentaerythritol or its dimers with monohydric alcohols; and the so-called complex esters which constitute various'combinations of dibasic acids, glycols and alcohols or dibasic acids, glycols and nonobasic acids.
• Table C outlines the various alternative structures contemplated as complex esters" as well as listing briefly typical starting materials for the formation of such esters.
• Alcohol-(dibasic acid-glycol)-monobasic acid R OOCR COOR -OOCR See UJS. 2,575,195 Alcohol-dibasic acid-(glycol-dibasic acid) -alcohol 4 R OOCR COO(R -OOR COO) R See US. 2,703,811 Monobasic acid-glycol-(dibasic acid-glycol) monobasic acid R COOR -(OOCR COO--R -OOCR See US. 2,575,196 Monohydric alcohols:
• Sebacic acid Azelaic acid As diesters there may be used one or more of the compounds of the formula ROOC-Z-COOR wherein Z is an alkylene chain of four to eight carbon atoms and R is an alkyl group of four to fourteen carbon atoms, being the residue of an aliphatic monohydric alcohol from butyl to tetradecyl alcohols.
• Dicarboxylic acids which provide the above esters are adipic, pimelic, suberic, azelaic, and sebacic.
• the alcohols include butyl, isobutyl, or sec-butyl alcohols and the various amyl, hexyl, octyl, nonyl, decyl, undecyl, dodecyl, and tetradecyl alcohols.
• the alcohols with branched hydrocarbon chains provide diesters with particularly desirable properties.
• Typical of these are isobutyl, 2-ethylbutyl, 2-ethylhexyl, l-rnethylhexyl, l-methylheptyl, 1-methyl-4-ethyloctyl, 2,2, 4-trimethylhexyl, 2-isopropyl-3,3-dimethylbutyl, 1,4-dimethylbutyl, and 1-isobutyl-4-ethyloctyl alcohols.
• the aliphatic polyesters which may be utilized as the lubricating fluids are preferably tetraesters, such as the pentaerythritol esters or the dimers or trimers of the same.
• each radical contains from 4 to 18 carbon atoms each and preferably from 6 to 14 carbon atoms each.
• Typical species include pentaerythritol tetracaproate, dipentaerythritol hexavalerate, pentaerythritol tetraheptoate, pentaerythiritol dicaproate divalerate, pentaerythritol tricaproate heptoate and mixtures thereof.
• the esters may be either mixed esters or mixtures of homo esters, the best rheological properties being obtained with mixed esters and with mixtures of esters. For use at elevated temperatures the dipentaerythritol esters are preferred due to their greater molecular weight and consequently higher boiling points.
• the course of oxidation as indicated by the rate of oxygen absorption in the composition of this invention indicates that the amine in complex form with the copper salt is oxidized prior to its assumingits intended function of acting as an oxidation inhibitor.
• the oxidation of the amine may take place prior to or subsequent to incorporation of the amine in the ester base lubricant. Consequently, the invention will be understood to include the use of not only the amines per sebut also their oxidation products as' well as the copper complexes of such oxidized products.
• the fraction of the oxidized product found to be most active in the prevention of oxidation of the ester base lubricant has a nitrogen-to-copper molar ratio in the order of about 20-30, while the less effective fractions of the oxidized product have nitrogen-to-copper molar ratios in the order of 36.
• phenolic compounds may be modified by the presence of alkyl radicals on one or both of the phenolic nuclei. Typical compounds are as follows:
• EXAMPLE III Oxidation inhibition of a mix d pentaerythritol ester.-- A pentaerythritol ester of a mixture of fatty acids averaging C C per ester linkage was modified with 0.025 mol of 2,2-dip-yridylamine (22DPA) and with other TAB LE 1 Oxidation Inhibitor, 0.025 M time, hours 0 22-DgA/Cu acetate comple N Cu, Fe, Ag, AL- 68 o Copper octoate None 16 Metal washers.
• 22DPA 2,2-dip-yridylamine
• the pentaerythritol ester base fluid was modified with 0.025 mol of benzoguanamine per liter of solution.
• the table which follows shows the effect upon oxidation inhibition of adding copper octoate to this composition. Copper octoate added in this manner forms a complex with a part of the amine in situ.
• the above material was separated into 4 fractions by solvent extraction.
• the first portion was insoluble in ethanol, M.P. 400 C.
• Dilution of the alcohol solution with water gave a water insoluble second fraction, M.P. 132-135 C.
• the third portion was a precipitate obtained by adding ether to an ethanol solution of fraction 2, M.P. 18l-l92 C.
• the filtnate of fraction 3 gave fraction 4 on evaporation of solvent; it was a dark green viscous liquid and was ether, water and ethanol soluble.
• a synthetic ester base lubricant composition comprising a major proportion of a pentaerythritol tetraester of a fatty acid and minor oxidation-inhibiting proportions each of benzoguanamine and a copper octoate complex with benzoguanamine, the mol ratio of total amine to copper being between about 5 and about 35.
• a synthetic ester base lubricant composition comprising a major proportion of a pentaerythritol tetraester of a fatty acid and minor oxidation-inhibiting proportions each of 2,2-dipyridylamine and a copper diacet-ate complex with 2,2'-dipyridylamine, the mol ratio of total amine to copper being between about 5 and about 35.
• a synthetic ester base lubricant composition comprising a major proportion of a pentaerythritol tetraester of a fatty acid and minor oxidation-inhibiting proportions each of an aryldiaminotriazine and a copper complex of a copper C 24 fatty acid salt with a triazine, the mol ratio of total amine to copper being between about 5 and about 35.
• a synthetic ester base lubricant composition comprising .a major proportion of a pentaerythritol tetraester of a fatty acid and minor oxidation-inhibiting proportions each of 2,2'-dipyridylamine and a copper dioctoate complex with 2,2'-dipyridylamine, the mol ratio of total amine to copper being between about 5 and about 35.
• a synthetic ester base lubricant composition comprising a major proportion of a pentaerythritol tetraes-ter of a fatty acid and minor oxidation-inhibiting proportions each of 2,2'-dipyridylamine and a copper C -24 fatty acid salt complex with 2,2'-dipyridylamine, the mol ratio of total amine to copper being between about 5 and about 35.
• a synthetic ester base lubricant composition comprising a major proportion of a pen-taerythritol ester of an aliphatic monocarboxylic acid and minor oxidationinhibiting amounts each of diaminotriazine and a copper C 24 fatty acid salt complex with a pyridylamine, the mol ratio of total amine to copper being between about 2 and about 75.
• a synthetic ester base lubricant composition comprising a major proportion of a pentaerythritol ester and minor oxidation-inhibiting amounts each of a triazine and a copper C 24 fatty :acid salt complex, with a pyridylamine, the mol ratio of total amine to copper being between about 2 and about 75.
• a synthetic ester base lubricant composition comprising a major proportion of a pentaerythritol ester and minor oxidation-inhibiting amounts each of a pyridylamine and a copper C 24 fatty acid salt complex with a pyridylamine, the mol ratio of 'total amine to copper being between about 2 and about 75.
• a synthetic ester base lubricant composition comprising (a major proportion of a pentaerythritol ester of an aliphatic monocarboxylic acid and minor oxidationinhibiting amounts each of a dipyridylamine and a copper of the same group, the mol ratio of total amine to cop- 10 per being between about 2 and about 75.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Lubricants (AREA)

Priority Applications (7)

Applications Claiming Priority (1)

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Cited By (10)

Citations (3)

• 0
  • BE BE604610D patent/BE604610A/xx unknown
  • NL NL265537D patent/NL265537A/xx unknown
• 1960
  • 1960-06-06 US US33952A patent/US3093585A/en not_active Expired - Lifetime
• 1961
  • 1961-06-05 GB GB20209/61A patent/GB942161A/en not_active Expired
  • 1961-06-05 FR FR863909A patent/FR1297944A/fr not_active Expired
  • 1961-06-05 DE DES74206A patent/DE1146995B/de active Pending
  • 1961-06-05 DE DES81917A patent/DE1148684B/de active Pending

Patent Citations (3)

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