US3660290A - Lubricant compositions - Google Patents
Lubricant compositions Download PDFInfo
- Publication number
- US3660290A US3660290A US860035A US3660290DA US3660290A US 3660290 A US3660290 A US 3660290A US 860035 A US860035 A US 860035A US 3660290D A US3660290D A US 3660290DA US 3660290 A US3660290 A US 3660290A
- Authority
- US
- United States
- Prior art keywords
- alkylphenyl
- naphthylamine
- alkyl
- naphthylamines
- 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
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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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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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
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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- 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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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
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- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/283—Esters of polyhydroxy compounds
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- C10M2207/285—Esters of aromatic polycarboxylic acids
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- C10M2207/286—Esters of polymerised unsaturated acids
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- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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- C10M2215/064—Di- and triaryl amines
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- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
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- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- C10M2229/02—Unspecified siloxanes; Silicones
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- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- This invention relates to a novel class of phenyl-2- befo re described alkylphenyl-alkylnaphthylammes with naphtllylamme denvatlves and to 1ubnant comPosltlons 20 phenyl-2-naphthylamines having alkyl substituents exclucontainlng such compounds.
- alkyl groups may contain from 2 to 16 carbon lubricating 0115 has led to the development of numerous atoms, but Preferably having 4 to 12 carbon atoms and oxidation inhi it for eXample Phenothiazine, phenyl a tertiary alkyl structure.
- Certain alkylated phenyl-Z-naphthylamines stituted in the 4 position of the phenyl ring have been have also been Proposed these alkylated compounds found to be particularly elfective when used in combinaing Characterized by having one or more alkyl Substitu' tion with the present additives. Examples of such coments introduced into the phenyl nucleus. With the conpounds include:
- naphthylamines are efiective in improving the oxidation resistance, cleanliness and bearing performance properties 11 D y aph y mnine of lubricatin oils.
- the eifectiveness of these com unds g p0 and the like.
- the alkylphenyl-alkylnaphthylamines of the invention are generally prepared by reacting phenyl-2-naphthyl R1 amine with a 1- or 2-alkene having from 2 to 16, or more, carbon atoms at an elevated temperature in the presence of a Friedel-Crafts catalyst, e.g., aluminum chloride.
- a Friedel-Crafts catalyst e.g., aluminum chloride.
- the H reaction conditions largely govern the nature of the alkylated products formed. Conditions conducive to naphthyl wherein R and R are alkyl groups having from 2 to 80, ring substitution are described in Example 1. Employing preferably from 2 to 16, carbon atoms.
- the alkylphenyl-alkylnaphthylamines of the invention boxylic acids having from 3 to 20, especially 4 to 12 carcan be employed in lubricant compositions either singubon atoms.
- the ester base may comprise a simple ester larly, in mixtures, or in combination with alkylphenyl-2- (reaction product of a monohydroxyalcohol and a mononaphthylamines which have alkyl substituents exclusively carboxylic acid), a polyester (reaction productof an alon the phenyl nucleus.
- cohol and an acid one of which has more than one functional group
- a complex ester reaction product of a polyfunctional acid with more than one alcohol, or of a polyfunctional alcohol with more than one acid.
- excellent synthetic lubricant may be formulated from mixtures of esters, such as major proportions of complex esters and minor amounts of diesters.
- ester base oils examples include ethyl palmitate, ethyl laurate, butyl stearate, di(2-ethylhexyl)sebacate, di (2-ethylhexyl)azelate, ethylene glycol diluarate, di-(Z-ethylhexyl)phthalate, di-(3-methylbutyl) adipate, di-(Z-ethylpropyl)azelate, diisopropyloxylate, dicyclohexyl sebacate, glycerol tri-n-heptanoate, di(undecyl)azelate, and tetraethylene glycol di-(2-ethy1 hexanoate), and mixtures thereof.
- An especially preferred mixture of esters consists of about 50 80% bis(2,2,4 trimethylpentyl)azelate and 20 to 50% 1,1,1'trimethyl propane triheptanoate.
- esters for use as base stocks in the present invention are esters of monocarboxylic acids having 3 to 12 carbons and polyalcohols such as pentaerythritol, dipentaerythritol, trimethylolpropane and mixtures thereof.
- esters examples include pentaerythrityl tetrabutyrate, pentaerythrityl tetravalerate, pentaerythrityl tetracaproate, pentaerythrityl dibutyratedicaproate, pentaerythrityl butyratecaproate divalerate, pentaerythrityl butyrate trivaler-ate, .pentaerythrityl butyrate tricaproate, pentaerythrityl tributyratecaproate, mixed C -C saturated fatty acid esters of pentaerythritol, dipentaerythrityl hexavalerate, dipentaerythrityl hexacaproate, dipentaerythrityl hexaheptoate, dipentaerythirtyl hexacaprylate, dipentaerythrityl tributyratetricaproate, dipentaerythrity
- the additives of this invention may also be incorporated in mineral lubricating oils.
- the mineral lubricating oil can be obtained from parafiinic, naphthenic, asphaltic or mixed base crudes and/or mixtures thereof, for example neutral oils having viscosities of from 100 to 6500 SSU at 100 F.
- the alkylpienyl-alkylnaphthylamines of the invention can be incorporated into lubricant compositions in amounts of from 0.01 to 10% by weight of the total composition. Concentrations of 0.5 to 5.0% by weight are generally sufiicient to impart the desired properties to lubricating oils. These concentration ranges are also ap plicable to mixtures of alkylphenyl-alkylnaphthylamines with alkylphenyl-naphthylamines as hereinbefore described.
- a preferred embodiment of the invention therefore is an ester base lubricating composition containing a total of from 0.01 to 10% by weight of a mixture of one or more 4-a1kylphenyl-1-alkyl-2-naphthylamines with one or more 4-alkylphenyl-Z-naphthylamines, the ratio of the former compounds to the latter being from 1:2 to 10:1.
- additives recognized in the art to perform a particular function or functions can also be incorporated into the present compositions. These include viscosity improvers, e.g., methacrylate polymers and copolymers, additional antioxidants, corrosion inhibitors, antifoam agents, detergents and the like.
- EXAMPLE I 5.36 g. (0.04 mole) of aluminum trichloride was added to 87.6 g. (0.4 mole) of phenyl-2-naphthylamine and heated to 120 C. While stirring and under a nitrogen atmosphere, 89.6 g. (0.8 mole) of diisobutylene was added dropwise to the reaction mixture over a period of one hour. After the addition of the diisobutylene, the reaction mixture was heated to 148 C. over a three hour period and the temperature maintained there for an additional two hours.
- Additive B Mixture of 4-tert-octylphenyl-1-tert-octyl-2- naphthylamine, 4 tert-butylphenyl-l-tert-octy1-2-naphthylamine and 4-tert-octylphenyl-1-tert-butyl-2-naphthylamine with 4 tert-octylphenyl-Z-naphthylamine, Ratio of alkylphenyl-alkylnaphthylamines to 4-tertoctylpheny1-2-naphthylamine is approximately 3 to 1.
- Base Oils Base Oil W Mixed C acid esters of pentaerythritol and dipentaerythritol containing 0.17% w. of phosphorus extreme pressure agents, 0.1% w. of triazole corrosion inhibitors, 0.25% w. of a copolymeric dispersant, 1.5% W. of an amine antioxidant, 0.02% of a. dibasic acid corrosion inhibitor and 10 ppm. silicone fiuid antifoamant.
- Base Oil X Base Oil W minus the copolymeric dispersant plus 2.0% w. additional phosphorus extreme pressure agent.
- Base Oil Y Base Oil X minus the dibasic acid corrosion inhibitor and 1.0% of phosphorus extreme pressure agent plus 0.5% w. of a triazine oxidation inhibitor and an additional 0.5 of the amine antioxidant.
- Base Oil Z Mixed C acid esters of pentaerythritol and dipentaerythritol containing 0.2% W. phosphorus extreme pressure agent and 0.5 w. of a triazole corrosion inhibitor.
- compositions V and VI of the invention have outstanding properties in respect to overall cleanliness and viscosity change as compared to Composition IV whech contains an equal molar concentration of a phenyl-Z-naphthylamine having no alkyl substituents on the naphthyl ring. It is indeed surprising that the addition of an alkyl substituent on the naphthyl nucleus (Additive A) would bring about such a significant improvement in the eifectiveness of the inventive compounds.
- Composition VI which contains a combination of the additives of the invention with the additive employed in Composition IV, has an overall demerit rating superior to that of either Compositions IV or V containing the additives individually, i.e., a total demerit rating of 28.2 as compared to 69 and 38.6 respectively.
- EXAMPLE IV A further indication of the stability of the compositions of the invention was obtained by subjecting samples of Compositions VII and VIII to the Alcor High Temperature Deposition Test. Basically this test involves circulation of aerated oil over a heated deposition tube. The temperature of the tube is controlled at 525 F. on the inlet side and reaches 650 to 700 F. at the outlet end of the tube. The temperature profile of the tube is measured at the start and shortly before the end of the test. These temperature profiles and the tube deposits per unit length are used to determine the performance of the oil. The critical temperature is that temperature at which deposits begin to significantly affect the heat transfer characteristics of the oil. A temperature of about 600 F. is considered to be very satisfactory.
- the overall deposit rating is obtained from a combination of the visual deposit rating of the tube, the tube deposit weight and the filter deposit weight. An overall rating of less than 50 is considered very good, a rating of below is considered exceptional. A detailed description of this test is given in Proceedings of the USAF-Southwest Research Institute Turbine Lubrication Conference, September 13-15, 1966, Southwest Research Institute, San Antonio, Texas, page 152. Test results are shown in Table III.
- composition VIII of the invention has a significantly less tendency to form deposits than Composition V-II which is prepared from the same base oil as Composition VIII but contains an alkylated phenyl-Z-naphthylamine not in accordance with the invention.
- compositions II and III of the invention have surprisingly less tendency to form sludge than Composition I which contains a molar equivalent of an additive not in accordance with the invention.
- Composition XI of the invention had a significantly longer oxidation life than either Composition IX containing phenyl-2-naphthylamine, or Composition X containing an equivalent amount of a phenyl-Z-naphthylamine having an alkyl substituent on the phenyl ring alone.
- a lubricant composition consisting essentially of a major amount of lubricating oil and an oxidation-inhibiting amount of a mixture of at least one 4-alkylphenyl-1- alkyl-2-naphthylamine with at least one 4-alkylphenyl-2- naphthylamine wherein said alkyl substituents have up to 16 carbon atoms and are tertiary alkyl substituents and the ratio of said alkylphenylalkylnaphthylamines to the alkylphenyl-naphthylamines is from 1:2 to 10:1.
- composition of claim 1 wherein the oxidation inhibiting mixture is present in the amount of from 0.01 to 10% by weight.
- composition of claim 1 wherein the lubricating oil is an ester of a monocarboxylic acid having 3 to 12 carbon atoms and a polyhydroxy compound selected from the group consisting of pentaerythritol, dipentaerythritol, trimethylolpropane and mixtures thereof.
- composition of claim 3 wherein all of the alkyl substituents are selected from the group consisting of tertiary-butyl and tertiary-octyl.
- composition of claim 4 wherein the ester lubricating oil is a mixed C acid ester of pentaerythritol and dipentaerythritol and the oxidation-inhibiting mixture is a mixture of 4-alkylphenyl-l-alkyl-Z-naphthylamines with 4-tert-octylphenyl-Z-napthylamine.
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Abstract
4-ALKYLPHENYL-ALKYL-2-NAPHTHYLAMINES AND MIXTURES OF 4-ALKYLPHENYL-1-ALKYL-2-MAPHTHYLAMINES WITH 4-ALKYLPHENYL-2-NAPHTHYLAMINES ARE EFFECTIVE IN IMPROVING THE OXIDATION RESISTANCE, CLEANLINESS AND BEARING PERFORMANCE PROPERTIES OF LUBRICANT COMPOSITIONS.
Description
United States Patent Oflice 3,660,290
Patented May 2, 1972 Exam les of the invent' 3,660,290 p we compounds include. LUBRICANT COMPOSITIONS t" Roland T. Schlo'bohm, Bethalto, Ill., assignor to Shell N O rr Oil Company, New York, NY. L i it No Drawing. Filed Sept. 22, 1969, Ser. No. 860,035
Int CL clom 1/34 i-octylphenyl-l-butyl-E-naphthy1amine U.S. Cl. 252-515 A 5 Claims 8 1-: J
N -C H @ioixffi a 1? ABSTRACT OF THE DISCLOSURE 10 h (m1 1 1 t l 2 uh 4-alkylphenyl-1-alkyl-2-naphthylamines and mixtures of 3 0c J thylamne 4-alkylphenyl-1-alky1-2-naphthylamines with 4-alkylphena 17 N yl-2-naphthylamines are effective in improving the oxida- W0 I I O 4439 tion resistance, cleanliness and bearing performance prop- H +-butylphenyl-l-octyl-E-naphthylamine and the like.
It has been further found that mixtures of the hereinerties of lubricant compositions.
This invention relates to a novel class of phenyl-2- befo re described alkylphenyl-alkylnaphthylammes with naphtllylamme denvatlves and to 1ubnant comPosltlons 20 phenyl-2-naphthylamines having alkyl substituents exclucontainlng such compounds. More particularly, it relates Sively on the phenyl ring also impart excellent perfonm to i i t i' 'i' w i m Whlch ance properties to ester base lubricant compositions; propfectrve 1n increasing the oxidation resistance, cleanliness erfies which in fact are Superior to those which would be and i' perfmmancapmgerfies of lubric?ting F expected from the use of these compounds individually. Lflbncants emploYed hlgh sPeed turbme g 5 Alkylphenyl-Z-naphthylamines which are suitable for partfcularly modem 2 alrFraft engme?! must be reslstant use in conjunction with the additives of the invention are to tempefratfre oxldatlve Search for those having one or more alkyl substituents on the phenyl add tives wh ch impart the requisite properties to such ring Said alkyl groups may contain from 2 to 16 carbon lubricating 0115 has led to the development of numerous atoms, but Preferably having 4 to 12 carbon atoms and oxidation inhi it for eXample Phenothiazine, phenyl a tertiary alkyl structure. Alkylphenyl-2-naphthylamines l-naphthylamine, phenyl-2-naphthylami and Various having a single tertiary-butyl or tertiary-octyl group subphenylamines. Certain alkylated phenyl-Z-naphthylamines stituted in the 4 position of the phenyl ring have been have also been Proposed these alkylated compounds found to be particularly elfective when used in combinaing Characterized by having one or more alkyl Substitu' tion with the present additives. Examples of such coments introduced into the phenyl nucleus. With the conpounds include:
tinual development of more powerful jet engines, however, and a corresponding increase in operating temperatures, many of the prior art additives have proved to be I inadequate in providing the required oxidation stability H to lubricating oils. Therefore, there is a need in the art 40 for the development of additives which will increase a 4-butylphenyl-Z-naphthylamine cause the formation of deposits.
It has now been found that 4-alkylphenyl-1-alkyl-2- lubricants resistance to oxidative degradation and which will not form sludge, develop high acidity or viscosity, or
naphthylamines are efiective in improving the oxidation resistance, cleanliness and bearing performance properties 11 D y aph y mnine of lubricatin oils. The eifectiveness of these com unds g p0 and the like. Compositions wherein the ratio of the alkylis attributed in substantial part to the presence of an alkyl substituent on the naphthyl nucleus which was found 0 f 'i i z i i to t P Substl to have a remarkable eifect on the performance character- P any P t y ammes 1s 3 to 1 very istics of the resulting compound. satisfactory especially those wherein the ratio is from 355 iggggfigigggt 2 naphthylamnes the m The alkylphenyl-alkylnaphthylamines of the invention are generally prepared by reacting phenyl-2-naphthyl R1 amine with a 1- or 2-alkene having from 2 to 16, or more, carbon atoms at an elevated temperature in the presence of a Friedel-Crafts catalyst, e.g., aluminum chloride. The H reaction conditions largely govern the nature of the alkylated products formed. Conditions conducive to naphthyl wherein R and R are alkyl groups having from 2 to 80, ring substitution are described in Example 1. Employing preferably from 2 to 16, carbon atoms. Compounds these conditions it is possible to introduce alkyl substituwherein the R and R substituents have from 4 to 12 ents into the naphthyl nucleus thus forming the unique carbon atoms and have a tertiary alkyl structure are compounds of the present invention. especially advantageous for use in the present composi- Lubricant base stocks suitable for the practice of the tions, particularly those wherein R and R are tertiarypresent invention include esters of alcohols having 1 to butyl or tertiary-octyl groups. 20, especially 4 to 12 carbon atoms andaliphatic car- The alkylphenyl-alkylnaphthylamines of the invention boxylic acids having from 3 to 20, especially 4 to 12 carcan be employed in lubricant compositions either singubon atoms. The ester base may comprise a simple ester larly, in mixtures, or in combination with alkylphenyl-2- (reaction product of a monohydroxyalcohol and a mononaphthylamines which have alkyl substituents exclusively carboxylic acid), a polyester (reaction productof an alon the phenyl nucleus. cohol and an acid, one of which has more than one functional group), or a complex ester (reaction product of a polyfunctional acid with more than one alcohol, or of a polyfunctional alcohol with more than one acid). Also, excellent synthetic lubricant may be formulated from mixtures of esters, such as major proportions of complex esters and minor amounts of diesters.
Examples of suitable ester base oils are ethyl palmitate, ethyl laurate, butyl stearate, di(2-ethylhexyl)sebacate, di (2-ethylhexyl)azelate, ethylene glycol diluarate, di-(Z-ethylhexyl)phthalate, di-(3-methylbutyl) adipate, di-(Z-ethylpropyl)azelate, diisopropyloxylate, dicyclohexyl sebacate, glycerol tri-n-heptanoate, di(undecyl)azelate, and tetraethylene glycol di-(2-ethy1 hexanoate), and mixtures thereof. An especially preferred mixture of esters consists of about 50 80% bis(2,2,4 trimethylpentyl)azelate and 20 to 50% 1,1,1'trimethyl propane triheptanoate.
Especially preferred esters for use as base stocks in the present invention are esters of monocarboxylic acids having 3 to 12 carbons and polyalcohols such as pentaerythritol, dipentaerythritol, trimethylolpropane and mixtures thereof. Examples of these esters are pentaerythrityl tetrabutyrate, pentaerythrityl tetravalerate, pentaerythrityl tetracaproate, pentaerythrityl dibutyratedicaproate, pentaerythrityl butyratecaproate divalerate, pentaerythrityl butyrate trivaler-ate, .pentaerythrityl butyrate tricaproate, pentaerythrityl tributyratecaproate, mixed C -C saturated fatty acid esters of pentaerythritol, dipentaerythrityl hexavalerate, dipentaerythrityl hexacaproate, dipentaerythrityl hexaheptoate, dipentaerythirtyl hexacaprylate, dipentaerythrityl tributyratetricaproate, dipentaerythrityl trivalerate tripelargonate, dipentaerythrityl mixed hexaesters of -0 fatty acids and trimethylyl-propane heptanoate. Mixtures of pentaerythrityl and dipentaerythrityl esters of C -C acids are particularly advantageous base oils, and are commercially available from Hercules, Inc.
In addition to the aforementioned synthetic oils, the additives of this invention may also be incorporated in mineral lubricating oils. The mineral lubricating oil can be obtained from parafiinic, naphthenic, asphaltic or mixed base crudes and/or mixtures thereof, for example neutral oils having viscosities of from 100 to 6500 SSU at 100 F.
The alkylpienyl-alkylnaphthylamines of the invention can be incorporated into lubricant compositions in amounts of from 0.01 to 10% by weight of the total composition. Concentrations of 0.5 to 5.0% by weight are generally sufiicient to impart the desired properties to lubricating oils. These concentration ranges are also ap plicable to mixtures of alkylphenyl-alkylnaphthylamines with alkylphenyl-naphthylamines as hereinbefore described. A preferred embodiment of the invention therefore is an ester base lubricating composition containing a total of from 0.01 to 10% by weight of a mixture of one or more 4-a1kylphenyl-1-alkyl-2-naphthylamines with one or more 4-alkylphenyl-Z-naphthylamines, the ratio of the former compounds to the latter being from 1:2 to 10:1.
Other additives recognized in the art to perform a particular function or functions can also be incorporated into the present compositions. These include viscosity improvers, e.g., methacrylate polymers and copolymers, additional antioxidants, corrosion inhibitors, antifoam agents, detergents and the like.
The invention will be further described by means of the following examples which demonstrate the manner of preparation and effectiveness of the inventive compounds and compositions. It should be understood, however, that these examples are given for illustrative purposes only and that the invention in its broader aspects is not limited thereto.
EXAMPLE I 5.36 g. (0.04 mole) of aluminum trichloride was added to 87.6 g. (0.4 mole) of phenyl-2-naphthylamine and heated to 120 C. While stirring and under a nitrogen atmosphere, 89.6 g. (0.8 mole) of diisobutylene was added dropwise to the reaction mixture over a period of one hour. After the addition of the diisobutylene, the reaction mixture was heated to 148 C. over a three hour period and the temperature maintained there for an additional two hours. The reaction mixture was then allowed to cool, mixed with two volumes of benzene, poured over ice and water, Washed with a 10% aqueous NaOH solu* tion and with distilled water until neutral, after which the benzene layer was dried over CaSO After filtering and removal of the benzene by distillation, the crude product (146 g.) was vacuum distilled over the range of 210/ 50 to 260 C./45/L, yielding 139 g. of product. 4-tertoctylphenyl-l-tert-octyl 2 naphthylamine was isolated by means of gas chromatographic preparative techniques and was identified by infra-red spectroscopy, nuclear magnetic resonance (NMR) and elemental analysis. This compound constituted 54.99% of the reaction product.
Gas chromatographic analysis also demonstrated the presence of a mixture of two other naphthyl-substituted henyI-Z-naphthylarnines constituting 15.79% of the reaction product. This mixture was separated from distilled product and identified by infra-red spectroscopy and nuclear magnetic resonance as being 4-tert-octylphenyl-ltert-butyl-2-naphthylamine and 4-tert-butylphenyl-l-tertoctyl-Z-naphthylamine.
EXAMPLE II TABLE I Additive, percent weight 4-tertoetyl- Phenylphenyl- 2-naph- Z-naph- Ease thyl thyl- Addi- Addi 01]. amine amine tive A tivo B 1 Equal molar concentrations equivalent to 1.0% w. phenyl-Z-naphthyl 2.1111116 in base oil.
Additives Additive 4-tert-octylphenyl-l-tert-octyl-Z-naphthylamine Additive B: Mixture of 4-tert-octylphenyl-1-tert-octyl-2- naphthylamine, 4 tert-butylphenyl-l-tert-octy1-2-naphthylamine and 4-tert-octylphenyl-1-tert-butyl-2-naphthylamine with 4 tert-octylphenyl-Z-naphthylamine, Ratio of alkylphenyl-alkylnaphthylamines to 4-tertoctylpheny1-2-naphthylamine is approximately 3 to 1.
Base Oils Base Oil W: Mixed C acid esters of pentaerythritol and dipentaerythritol containing 0.17% w. of phosphorus extreme pressure agents, 0.1% w. of triazole corrosion inhibitors, 0.25% w. of a copolymeric dispersant, 1.5% W. of an amine antioxidant, 0.02% of a. dibasic acid corrosion inhibitor and 10 ppm. silicone fiuid antifoamant.
Base Oil X: Base Oil W minus the copolymeric dispersant plus 2.0% w. additional phosphorus extreme pressure agent.
Base Oil Y: Base Oil X minus the dibasic acid corrosion inhibitor and 1.0% of phosphorus extreme pressure agent plus 0.5% w. of a triazine oxidation inhibitor and an additional 0.5 of the amine antioxidant.
Base Oil Z: Mixed C acid esters of pentaerythritol and dipentaerythritol containing 0.2% W. phosphorus extreme pressure agent and 0.5 w. of a triazole corrosion inhibitor.
EXAMPLE III To demonstrate the advantages of the present compositions in respect to oxidation stability and high temperature bearing performance, Compositions IV, V and VI, all prepared from Base Oil X, were subjected to a Bearing Rig Test under the very severe Type 2% conditions. The results of these tests are shown in Table II.
The Bearing Rig Test is described in Military Specification MIL-L-23699.
From the above data it is evident that Compositions V and VI of the invention have outstanding properties in respect to overall cleanliness and viscosity change as compared to Composition IV whech contains an equal molar concentration of a phenyl-Z-naphthylamine having no alkyl substituents on the naphthyl ring. It is indeed surprising that the addition of an alkyl substituent on the naphthyl nucleus (Additive A) would bring about such a significant improvement in the eifectiveness of the inventive compounds. Moreover, it is equally remarkable that Composition VI, which contains a combination of the additives of the invention with the additive employed in Composition IV, has an overall demerit rating superior to that of either Compositions IV or V containing the additives individually, i.e., a total demerit rating of 28.2 as compared to 69 and 38.6 respectively.
EXAMPLE IV A further indication of the stability of the compositions of the invention was obtained by subjecting samples of Compositions VII and VIII to the Alcor High Temperature Deposition Test. Basically this test involves circulation of aerated oil over a heated deposition tube. The temperature of the tube is controlled at 525 F. on the inlet side and reaches 650 to 700 F. at the outlet end of the tube. The temperature profile of the tube is measured at the start and shortly before the end of the test. These temperature profiles and the tube deposits per unit length are used to determine the performance of the oil. The critical temperature is that temperature at which deposits begin to significantly affect the heat transfer characteristics of the oil. A temperature of about 600 F. is considered to be very satisfactory. The overall deposit rating is obtained from a combination of the visual deposit rating of the tube, the tube deposit weight and the filter deposit weight. An overall rating of less than 50 is considered very good, a rating of below is considered exceptional. A detailed description of this test is given in Proceedings of the USAF-Southwest Research Institute Turbine Lubrication Conference, September 13-15, 1966, Southwest Research Institute, San Antonio, Texas, page 152. Test results are shown in Table III.
The foregoing results indicate that Composition VIII of the invention, has a significantly less tendency to form deposits than Composition V-II which is prepared from the same base oil as Composition VIII but contains an alkylated phenyl-Z-naphthylamine not in accordance with the invention.
EXAMPLE V In order to further evaluate the antioxidation and anticorrosion properties of the present compositions, a series of Corrosion and Oxidation Stability Tests were run in accordance with the procedures set forth in Military Specification MIL-b23699. In addition, Compositions IX, X, and XI were subjected to a Micro-Air Oxidation Test. In this test, air at the rate of 30 ml./min. was passed through a 20 g. sample of the test lubricant which was maintained at a temperature of 425 F. The results of the test are expressed as oxidation life of the lubricant, which is defined as the time required for the adsorption of 3 millimoles of oxygen per gram of oil sample. The results of the Micro-Air Oxidation Test and the Corrosion and Oxidation Stability Test are shown in Table IV.
TABLE IV [Corrosion and oxidation stability, 400 F., 72 hours] Composition- I II III Weigl {it change of specimens:
*It is evident from the Corrosion and Oxidation Test results, that Compositions II and III of the invention have surprisingly less tendency to form sludge than Composition I which contains a molar equivalent of an additive not in accordance with the invention. In the Micro-Air Oxidation Test, Composition XI of the invention had a significantly longer oxidation life than either Composition IX containing phenyl-2-naphthylamine, or Composition X containing an equivalent amount of a phenyl-Z-naphthylamine having an alkyl substituent on the phenyl ring alone.
I claim as my invention:
1. A lubricant composition consisting essentially of a major amount of lubricating oil and an oxidation-inhibiting amount of a mixture of at least one 4-alkylphenyl-1- alkyl-2-naphthylamine with at least one 4-alkylphenyl-2- naphthylamine wherein said alkyl substituents have up to 16 carbon atoms and are tertiary alkyl substituents and the ratio of said alkylphenylalkylnaphthylamines to the alkylphenyl-naphthylamines is from 1:2 to 10:1.
2. The composition of claim 1 wherein the oxidation inhibiting mixture is present in the amount of from 0.01 to 10% by weight.
3. The composition of claim 1 wherein the lubricating oil is an ester of a monocarboxylic acid having 3 to 12 carbon atoms and a polyhydroxy compound selected from the group consisting of pentaerythritol, dipentaerythritol, trimethylolpropane and mixtures thereof.
4. The composition of claim 3 wherein all of the alkyl substituents are selected from the group consisting of tertiary-butyl and tertiary-octyl.
5. The composition of claim 4 wherein the ester lubricating oil is a mixed C acid ester of pentaerythritol and dipentaerythritol and the oxidation-inhibiting mixture is a mixture of 4-alkylphenyl-l-alkyl-Z-naphthylamines with 4-tert-octylphenyl-Z-napthylamine.
8 References Cited UNITED STATES PATENTS 2,009,480 7/1935 Craig 252-50 3,052,632 9/1962 Loefiier 25251.5 A
3,121,691 2/ 1964 Eickemeyer 252-50 X 3,505,225 4/ 1970 Wheeler 25250 X 3,509,214 4/1970 Braid et a1. 252-50 X FOREIGN PATENTS 1,429,495 1/1966 France 252-50 DANIEL E. WYMAN, Primary Examiner W. J. SHINE, Assistant Examiner US. Cl. X.R. 252-50, 390, 401
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---|---|
US (1) | US3660290A (en) |
JP (1) | JPS4910962B1 (en) |
BE (1) | BE756024A (en) |
CA (1) | CA924328A (en) |
DE (1) | DE2005843C3 (en) |
FR (1) | FR2068867A5 (en) |
GB (1) | GB1296087A (en) |
NL (1) | NL7013904A (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3767575A (en) * | 1971-11-16 | 1973-10-23 | Mobil Oil Corp | Oxidation resistant lubricant compositions |
US3944492A (en) * | 1966-04-07 | 1976-03-16 | Uniroyal, Inc. | Lubricant compositions containing N-substituted naphthylamines as antioxidants |
USRE28805E (en) * | 1971-11-17 | 1976-05-11 | Mobil Oil Corporation | Lubricants containing amine antioxidants |
US3990985A (en) * | 1973-03-26 | 1976-11-09 | Hoechst Aktiengesellschaft | Stable and storable aqueous dispersions of primary aromatic amines, their preparation and use |
JPS5316710A (en) * | 1976-07-30 | 1978-02-16 | Uniroyal Inc | Liquid antioxidant |
US4770802A (en) * | 1986-02-04 | 1988-09-13 | Nippon Oil Co., Ltd. | Lubricating oil compositions |
US5283367A (en) * | 1989-08-30 | 1994-02-01 | Ciba-Geigy Corporation | Substituted 1,4-diamino-2-butene stabilizers |
US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
US6426324B1 (en) | 1993-12-15 | 2002-07-30 | Noveon Ip Holdings Corp. | Lubricant composition |
US20070142243A1 (en) * | 2005-12-21 | 2007-06-21 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine |
US20070142246A1 (en) * | 2005-12-21 | 2007-06-21 | Chevron Oronite Company Llc | Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions |
US20070142245A1 (en) * | 2005-12-21 | 2007-06-21 | Chevron Oronite Company Llc | Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions |
US20080318815A1 (en) * | 2007-06-20 | 2008-12-25 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a dairylamine |
EP2077315A1 (en) | 2007-12-20 | 2009-07-08 | Chevron Oronite Company LLC | Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant |
US20100152079A1 (en) * | 2007-12-20 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51111457U (en) * | 1975-03-05 | 1976-09-09 | ||
JPS5280751U (en) * | 1975-12-15 | 1977-06-16 | ||
JPS52171560U (en) * | 1976-06-18 | 1977-12-27 | ||
ES2050413T3 (en) * | 1989-08-30 | 1994-05-16 | Ciba Geigy Ag | AROMATIC BUTENYL AMIN STABILIZERS. |
GB2294696A (en) * | 1994-11-04 | 1996-05-08 | Exxon Research Engineering Co | Marine lubricant composition |
EP1937767B1 (en) * | 2005-10-11 | 2013-05-22 | Chemtura Corporation | Diaromatic amines |
US20080287328A1 (en) * | 2007-05-16 | 2008-11-20 | Loper John T | Lubricating composition |
-
0
- BE BE756024D patent/BE756024A/en unknown
-
1969
- 1969-09-22 US US860035A patent/US3660290A/en not_active Expired - Lifetime
-
1970
- 1970-02-09 JP JP45011067A patent/JPS4910962B1/ja active Pending
- 1970-02-09 GB GB1296087D patent/GB1296087A/en not_active Expired
- 1970-02-09 DE DE2005843A patent/DE2005843C3/en not_active Expired
- 1970-03-12 FR FR7008859A patent/FR2068867A5/fr not_active Expired
- 1970-09-21 NL NL7013904A patent/NL7013904A/xx not_active Application Discontinuation
- 1970-09-21 CA CA093647A patent/CA924328A/en not_active Expired
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3944492A (en) * | 1966-04-07 | 1976-03-16 | Uniroyal, Inc. | Lubricant compositions containing N-substituted naphthylamines as antioxidants |
US3767575A (en) * | 1971-11-16 | 1973-10-23 | Mobil Oil Corp | Oxidation resistant lubricant compositions |
USRE28805E (en) * | 1971-11-17 | 1976-05-11 | Mobil Oil Corporation | Lubricants containing amine antioxidants |
US3990985A (en) * | 1973-03-26 | 1976-11-09 | Hoechst Aktiengesellschaft | Stable and storable aqueous dispersions of primary aromatic amines, their preparation and use |
JPS5316710A (en) * | 1976-07-30 | 1978-02-16 | Uniroyal Inc | Liquid antioxidant |
US4770802A (en) * | 1986-02-04 | 1988-09-13 | Nippon Oil Co., Ltd. | Lubricating oil compositions |
US5492954A (en) * | 1989-08-30 | 1996-02-20 | Ciba-Geigy Corporation | Substituted 1,4-diamino-2-butene stabilizers and stabilized compositions |
US5283367A (en) * | 1989-08-30 | 1994-02-01 | Ciba-Geigy Corporation | Substituted 1,4-diamino-2-butene stabilizers |
US5391808A (en) * | 1989-08-30 | 1995-02-21 | Ciba-Geigy Corporation | Substituted 1,4-diamino-2-butene stabilizers |
US6426324B1 (en) | 1993-12-15 | 2002-07-30 | Noveon Ip Holdings Corp. | Lubricant composition |
US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
US7501386B2 (en) | 2005-12-21 | 2009-03-10 | Chevron Oronite Company, Llc | Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine |
US20070142243A1 (en) * | 2005-12-21 | 2007-06-21 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine |
US20070142246A1 (en) * | 2005-12-21 | 2007-06-21 | Chevron Oronite Company Llc | Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions |
US20070142245A1 (en) * | 2005-12-21 | 2007-06-21 | Chevron Oronite Company Llc | Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions |
US7285518B2 (en) | 2005-12-21 | 2007-10-23 | Chevron Oronite Company Llc | Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions |
US8003583B2 (en) | 2005-12-21 | 2011-08-23 | Chevron Oronite Company Llc | Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions |
EP2009082A2 (en) | 2007-06-20 | 2008-12-31 | Chevron Oronite Company LLC | Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine |
US7683017B2 (en) | 2007-06-20 | 2010-03-23 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine |
US20080318815A1 (en) * | 2007-06-20 | 2008-12-25 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a dairylamine |
EP2077315A1 (en) | 2007-12-20 | 2009-07-08 | Chevron Oronite Company LLC | Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant |
US20100152079A1 (en) * | 2007-12-20 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant |
US8623798B2 (en) | 2007-12-20 | 2014-01-07 | Chevron Oronite Company Llc | Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant |
Also Published As
Publication number | Publication date |
---|---|
FR2068867A5 (en) | 1971-09-03 |
DE2005843A1 (en) | 1971-03-25 |
DE2005843B2 (en) | 1980-07-17 |
CA924328A (en) | 1973-04-10 |
NL7013904A (en) | 1971-03-24 |
BE756024A (en) | 1971-03-11 |
DE2005843C3 (en) | 1981-05-14 |
GB1296087A (en) | 1972-11-15 |
JPS4910962B1 (en) | 1974-03-14 |
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