Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Sulfurized compound of indeterminate structure – which is a...
Reexamination Certificate
1999-06-03
2002-02-19
McAvoy, Ellen M. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Sulfurized compound of indeterminate structure, which is a...
C508S331000, C508S460000
Reexamination Certificate
active
06348438
ABSTRACT:
The present invention relates to the production of highly overbased, alkaline earth metal, single-aromatic ring, hydrocarbyl salicylate-carboxylates. Specifically, it relates to a highly overbased calcium, single-aromatic ring, alkylsalicylate-stearate.
BACKGROUND OF THE INVENTION
The preparation of phenate-stearates is well known in the art.
European Patent Application No. 0,094,814 A2 teaches improving the stability of an overbased phenate by treating the phenate with a carboxylic acid having a C
10
to C
24
unbranched segment, such as stearic acid.
PCT Patent Applications WO 88/03944 and 88/03945 teach an overbased phenate having a TBN of more than 300. This high TBN is achieved by using an additional component: either a carboxylic acid, such as stearic acid, or a di- or poly carboxylic acid having from 36 to 100 carbon atoms, or an anhydride, acid chloride, or ester thereof.
The preparation of alkylsalicylates is also well known in the art.
U.S. Pat. No. 3,036,971 discloses preparing detergent dispersant additives based on sulfurized alkylphenates of high basicity alkaline earth metals. These additives are prepared by sulfurization of an alkylphenol, neutralization of the sulfurized alkylphenol with an alkaline earth metal base, then super-alkalization by carbonation of the alkaline earth metal base dispersed in the sulfurized alkylphenate.
French patent 1,563,557 discloses detergent additives based on sulfurized calcium alkylsalicylates. These additives are prepared by carboxylation of a potassium alkylphenate, exchange with calcium chloride, then sulfurization of the calcium alkylsalicylate obtained with sulfur in the presence of lime, a carboxylic acid and an alkylene glycol or alkyl ether of alkylene glycol.
French patent application 2,625,220 discloses superalkalized detergent-dispersant additives based on alkylphenates and alkylsalicylates. These additives are prepared by neutralization of an alkylphenol with an alkaline earth metal base in the presence of an acid and a solvent, distillation of the solvent, carboxylation, sulfurization and superalkalization by sulfur and an alkaline earth metal base in the presence of glycol and solvent, followed by carbonation and filtration.
PCT patent application PCT/FR95/00299 discloses a process that is able to improve substantially the performance of these additives, particularly in the tests relating to foaming, compatibility and dispersion in a new oil, and in the tests of stability towards hydrolysis. This process comprises neutralization with alkaline earth metal base of a mixture of linear and branched alkylphenols in the presence of a carboxylic acid, carboxylation by the action of carbon dioxide of the alkylphenate, followed by sulfurization and super-alkalization, then carbonation, distillation, filtration, and degassing in air.
European Patent Application No. 98 400 203.0 discloses an unsulfurized, alkali metal-free detergent-dispersant additive, comprising a mixture of alkaline earth metal salts (alkylphenate/alkylsalicylate) and unreacted alkylphenol. This additive improves antioxidant properties, high temperature deposit control, and black sludge control.
The addition of aliphatic carboxylic acids during the preparation of lubricating oil detergents is known. The resulting detergents can be referred to as carboxylic acid modified detergents and a variety of such detergents are known. The incorporation of aliphatic carboxylic acids into such detergents is known to modify theirs physical and/or performance properties. The most common physical modification observed by the incorporation of a fatty acids into detergents, which is also the most common reason for performing this modification, is an increase in the TBN of the detergent without deleteriously increasing the viscosity of the product to an unacceptable level.
U.S. Pat. No. 3,493,516 discloses the use of short chain carboxylic acids in the production of overbased phenates, which allows an increase in the TBN without excessive viscosity increase.
European Patent Application No. 385,616 discloses the use of fatty acids in the production of overbased phenates from alkylphenols or phenates with increased TBN's and acceptable viscosity.
European Patent Application No. 351,052 discloses the use of long chain carboxylic acids in the production of overbased salicylate detergents with TBN's greater than 300 and viscosity's less than 1000 cSt at 100° C.
European Patent Application No. 347,104 discloses the use of long chain carboxylic acids to produce overbased carboxylic modified low overbased sulphonates and/or phenates and/or salicylate detergents with improved deposit forming properties.
European Patent Application No. 347,103 discloses a process for producing carboxylic acid modified overbased phenates with TBN's greater than 350 and viscosities less than 1000 cSt at 100° C. starting from a phenate.
European Patent Application No. 351,053 discloses the production of carboxylic acid modified overbased sulphonates with TBN's greater than 300 and viscosities less than 1000 cSt at 100° C. that have better filtration processing characteristics.
U.S. Pat. No. 5,716,914 discloses a process for producing a carboxylic acid modified overbased phenate with TBN's greater than 300 and viscosities less than 1000 cSt at 100° C.
U.S. Pat. No. 5,069,804/European Patent Application No. 0,094,814 discloses a process for the production of carboxylic acid modified overbased phenates with improved foaming properties.
U.S. Pat. No. 5,714,443 discloses a process for the production of carboxylic acid modified overbased phenates with TBN's greater than 350 and viscosites less than 1000 cSt at 100° C.
U.S. Pat. No. 5,433,871 discloses a process for the production of carboxylic acid modified overbased mixed detergents (phenate and/or salicylate and/or napthenate and/or sulfonate) with TBN's greater than 300.
SUMMARY OF THE INVENTION
The present invention provides process for producing an overbased alkaline earth metal single-aromatic ring hydrocarbyl salicylate-carboxylate useful for improving the compatibility with sulfonates, solubility in severe base stocks, BN retention, and thermal oxidation stability of a lubricating oil.
That process comprises contacting a mixture comprising an alkaline earth metal single-aromatic ring hydrocarbyl salicylate, at least one solvent, metal hydroxide, and an alkyl polyhydric alcohol containing from one to five carbon atoms with carbon dioxide under overbasing reaction conditions. The overbased alkaline earth metal single-aromatic ring hydrocarbyl salicylate is treated, before, during, or subsequent to overbasing, with a long-chain carboxylic acid, anhydride, or salt thereof to form an alkaline earth metal single-aromatic ring hydrocarbyl salicylate-carboxylate.
Preferably, the alkaline earth metal single-aromatic ring hydrocarbyl salicylate is a single-aromatic ring alkylsalicylate. More preferably, it is a sulfurized calcium single-aromatic ring alkylsalicylate.
Preferably, the metal hydroxide is an alkaline earth metal hydroxide. More preferably, it is calcium hydroxide.
Preferably, the mixture further comprises a metal chloride, more preferably an aqueous metal chloride. Preferably, the metal chloride is an alkaline earth metal chloride, more preferably calcium chloride.
Preferably, the alkyl polyhydric alcohol is ethylene glycol.
Preferably, the mixture further comprises a hydrocarbyl phenate, more preferably an alkaline earth metal alkylphenate, most preferably a sulfurized calcium alkylphenate.
Preferably, the mixture further comprises a hydrocarbyl phenol, more preferably an alkylphenol.
Preferably, the mixture further comprises a double-aromatic ring hydrocarbyl salicylate wherein the mole ratio of single-aromatic ring hydrocarbyl salicylate to double-aromatic ring hydrocarbyl salicylate is at least 8:1.
Preferably, the long-chain carboxylic acid is stearic acid.
The overbased alkaline earth metal single-aromatic ring hydrocarbyl salicylate-carboxylate prepared by this process can be used in a lubricating oil
Campbell Curt B.
Le Coent Jean-Louis Marie
Triconnet Thierry
Caroli Claude J.
Chevron Oronite S.A.
McAvoy Ellen M.
Sheridan Richard J.
Stokley Linda A.
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