Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Organic -co- compound
Reexamination Certificate
1995-12-13
2002-01-22
McAvoy, Ellen M. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Organic -co- compound
C508S516000
Reexamination Certificate
active
06340659
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to lubricants particularly for high temperature engines, ceramic engines, or natural gas engines, where the lubricant includes a salt of certain adducts of glyoxylic acids and phenols.
Adducts of glyoxylic acids and phenols are known. For example, U.S. Pat. No. 5,281,346, Adams, Jan. 25, 1994, discloses a two-cycle engine lubricant comprising alkali or alkaline earth metal salts of carboxylic aromatic acids having a formula
wherein T is selected from the group consisting of
U.S. Pat. No. 5,356,546, Blystone et al, Oct. 18, 1994, discloses metal salts similar to those of U.S. Pat. No. 5,281,346. The salts find utility in lubricants and fuels other than 2-cycle engine lubricants and fuels.
U.S. Pat. No. 5,175,312, Dubs et al., Dec. 29, 1992, discloses 3-phenylbenzofuran-2-ones which are suitable for stabilizing organic material against oxidative, thermal, and actinic degradation. The materials are of the structure
The R groups can be, among other things, alkyl groups. Z can be substituted phenyl.
U.S. Pat. No. 3,862,133, Layer, Jan. 21, 1975, discloses y lactones of o-hydroxyphenylacetic acids, prepared by reacting a hydroxybenzene compound and glyoxal using an acidic catalyst. R substituents on the hydroxybenzene can include alkyl. The products may be used to prepare new rubbers and plastics by ring opening polymerization. 4,7-di-t-butyl-5-hydroxybenzofuran-2(3H)-one has antioxidant activity and acts as a stabilizer.
U.S. Pat. No. 3,038,935 to Gerber et al. teaches the preparation of compounds of the formula
wherein each R is an aliphatic, cycloaliphatic or aromatic radical, Me is Na, K or Li, by reacting alkali metal salts of hindered phenols with dichloroacetic acid. Products are said to be useful for production of rubber auxiliaries, mineral oil additives and stabilizers for plastics.
U.S. Pat. No. 2,320,241, Jenkins, May 25, 1943, discloses a lubricating oil composition which includes lactone forming acids of the type represented by
SUMMARY OF THE INVENTION
The present invention provides a process for lubricating an engine which contains at least one ceramic part which requires lubrication, comprising supplying to said part a lubricant composition comprising (a) a major amount of an oil of lubricating viscosity, and (b) a minor amount of a salt of the reaction product of (i) an aliphatic carbonyl carboxylic compound and (ii) a hydroxyaromatic compound, at least a portion of the molecules of which are alkyl-substituted.
The present invention also provides a process for lubricating an internal combustion engine which operates at a temperature of at least 250° C. at the top ring reversal position, or for lubricating a natural gas powered internal combustion engine, comprising supplying to said engine the above-described lubricant.
The invention further provides a composition of matter comprising a salt of the reaction product of (i) an aliphatic carbonyl carboxylic compound and (ii) a hydroxyaromatic compound containing at least two hydrocarbyl substituents each having at least 4 carbon atoms, at least a portion of the molecules of which are substituted with an alkyl group of at least 8 carbon atoms, said hydroxyaromatic compound further containing a tertiary alkyl group in a position ortho to the hydroxy group.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to lubricants and lubricant additives specially designed for use with certain demanding engines, including high temperature engines, ceramic engines, and natural-gas fueled engines. A key to the lubrication of such engines is supplying a lubricant containing additives which exhibit good performance at high temperatures. The additives of the present invention comprise (a) a major amount of an oil of lubricating viscosity, and (b) a minor amount of a salt of the reaction product of (i) an aliphatic carbonyl carboxylic compound and (ii) a hydroxyaromatic compound, at least a portion of the molecules of which are alkyl-substituted.
The oil of lubricating viscosity can include natural and synthetic lubricating oils and mixtures thereof. Natural oils include animal oils, vegetable oils, mineral lubricating oils, solvent or acid treated mineral oils, and oils derived from coal or shale. Synthetic lubricating oils include hydrocarbon oils, halo-substituted hydrocarbon oils, alkylene oxide polymers, esters of carboxylic acids and polyols, esters of polycarboxylic acids and alcohols, esters of phosphorus-containing acids, polymeric tetrahydrofurans, silicon-based oils and mixtures thereof.
Specific examples of oils of lubricating viscosity are described in U.S. Pat. No. 4,326,972. A basic, brief description of lubricant base oils appears in an article by D. V. Brock, “Lubricant Base Oils”,
Lubrication Engineering
, volume 43, pages 184-185, March, 1987.
In a preferred embodiment the oil of lubricating viscosity is an ester. A variety of ester lubricants are known and have been employed for their superior thermal stability properties. The ester lubricant of the present invention preferably contains at least one carboxylic ester of a monocarboxylic acylating agent, preferably having 4 to 15 carbon atoms, or alternatively a combination of a dicarboxylic acylating agent and a monocarboxylic acylating agent, again preferably having 4 to 15 carbon atoms, with a polyhydroxy compound containing at least two hydroxyl groups. The ester is characterized by the general formula
[R
1
COO]
n
R
In the above formula, R is a hydrocarbyl group, each R
1
is independently hydrogen, a straight chain hydrocarbyl group, a branched chain hydrocarbyl group, each preferably containing from 3 to 14 carbon atoms, or a carboxylic acid- or carboxylic ester-containing hydrocarbyl group, and n is at least 2.
The carboxylic ester lubricants utilized in the present invention are thus the reaction products of one or more carboxylic acylating agents, e.g. acids, anhydrides, acid chloride, or lower esters such as methyl or ethyl, with polyhydroxy compounds containing at least two hydroxyl groups. The polyhydroxy compounds may be represented by the general formula
R(OH)
n
wherein R is a hydrocarbyl group and n is at least 2. The hydrocarbyl group will preferably contain 4 to 20 or more carbon atoms, and the hydrocarbyl group may also contain one or more nitrogen and/or oxygen atoms. The polyhydroxy compounds generally will contain from 2 to 10 hydroxyl groups and more preferably from 3 to 10 hydroxyl groups.
The polyhydroxy compound may contain one or more oxyalkylene groups, and, thus, the polyhydroxy compounds include compounds such as polyetherpolyols. The number of carbon atoms and number of hydroxyl groups contained in the polyhydroxy compound used to form the carboxylic esters may vary over a wide range.
The polyhydroxy compounds used in the preparation of the carboxylic esters may also contain one or more nitrogen atoms. For example, the polyhydroxy compound may be an alkanolamine containing from 3 to 6 hydroxyl groups. In one preferred embodiment, the polyhydroxy compound is an alkanolamine containing at least two hydroxyl groups and more preferably at least three hydroxyl groups.
Specific examples of polyhydroxy compounds useful in the present invention include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, glycerol, neopentyl glycol, 1,2-, 1,3- and 1,4-butanediols, glycerol, pentaerythritol, dipentaerythritol, tripentaerythritol, triglycerol, trimethylolpropane, di-trimethylolpropane, sorbitol, inositol, hexaglycerol, decaglycerol, 2,2,4-trimethyl-1,3-pentanediol, etc. Preferably, the mixtures of any of the above polyhydroxy compounds can be utilized.
The carboxylic acylating agents utilized in the preparation of the carboxylic esters useful in the liquid compositions can be characterized by the following general formula
R
1
COOH
wherein R
1
is hydrogen, a hydrocarbyl group (including alkyl, aryl, and alkaryl hydrocarbyl groups), preferably of 3 to 14 carbon atoms, or a carboxylic acid- or carboxylic acid ester-contain
Bardasz Ewa A.
Blystone Sheri L.
DeTar Marvin B.
Kocsis Jody A.
Esposito Michael F.
McAvoy Ellen M.
Shold David M.
The Lubrizol Corporation
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