Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Organic compound containing boron
Reexamination Certificate
2001-01-16
2001-10-30
Howard, Jacqueline V. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Organic compound containing boron
C508S578000, C508S584000, C508S585000, C508S586000
Reexamination Certificate
active
06310009
ABSTRACT:
FIELD OF THE INVENTION
The present invention provides certain saligenin derivatives used in lubricating compositions. Heavy duty diesel engine oil formulations that contain, especially, borated or non-borated magnesium saligenin derivatives of the present invention exhibit significantly improved seal compatibility and reduced copper and lead corrosion. They also exhibit improved upper piston deposit performance, which can minimize excessive oil consumption and piston scuffing and can improve engine life.
BACKGROUND OF THE INVENTION
Saligenin, also known as salicyl alcohol and o-hydroxybenzyl alcohol, is represented by the structure
U.S. Pat. No. 2,250,188 (Wilson, Jul. 22, 1941) relates to mineral lubricating oils modified by addition of constituents to impart characteristics adapting them to conditions such as found in Diesel engines. In the lubricating oil is dissolved a small quantity of the calcium or other oil-soluble salt of the condensation product of formaldehyde with an alkyl phenol in which the alkyl group contains preferably 4 or 5 carbon atoms to insure oil solubility. Other metals than calcium, particularly the other alkaline earth metals and the light metals aluminum and zinc, may be employed in the formation of the oil-soluble metal salts.
U.S. Pat. No. 3,256,183 (Greenwald, Jun. 14, 1966) relates to lubricant compositions for use in engines of the diesel type, which include, among other components, an oil-soluble calcium phenate compound prepared by the process comprising the steps of reacting a mixture comprising 1 mole of an alkyl phenol and from about 1 to about 2 moles of a formaldehyde producing reagent in the presence of a catalyst at a temperature of from about 10° C. to about 99° C. and thereafter reacting said mixture with a calcium reagent selected from the class consisting of calcium hydroxide and calcium oxide at a temperature of at least about 30° C.
U.S. Pat. No. 5,516,441 (Denis, May 14, 1996) relates to a metal salt or boron compound of a hydrocarbyl-substituted aromatic hydroxy compound having at least two hydroxy-substituted aromatic rings bridged by sulfur, where at least one aromatic ring bears a substituent ortho to a hydroxy group, provides a useful lubricant additive. The substituent on the aromatic ring is an &Dgr;-hydroxy aliphatic hydrocarbyl group or a —C(O)R
2
group, where R
2
is hydrogen or aliphatic hydrocarbyl. Reaction of aldehyde with the sulfur-coupled aromatic hydroxy compound should be conducted under non-condensing conditions. Preferred salts are magnesium.
SUMMARY OF THE INVENTION
The present invention provides a composition comprising a saligenin derivative represented by the formula
wherein each X independently is —CHO, or —CH
2
OH, each Y independently is —CH
2
— or —CH
2
OCH
2
—, and wherein such —CHO groups comprise at least 10 mole percent of the X and Y groups;
each M is independently hydrogen, ammonium, or a valence of a metal ion;
each R
1
is independently a hydrocarbyl group containing 1 to 60 carbon atoms;
m is 0 to 10; and
each p is independently 0, 1, 2, or 3;
provided that at least one aromatic ring contains an R
1
substituent and that the total number of carbon atoms in all R
1
groups is at least 7;
further provided that if m is 1 or greater, then one of the X groups can be —H.
The invention further provides a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of the above saligenin derivative.
The invention further provides a process for preparing a saligenin derivative as above, particularly where M is magnesium, comprising combining a phenol substituted by said R
1
group with formaldehyde or a source of formaldehyde and magnesium oxide or magnesium hydroxide under reactive conditions, in the presence of a catalytic amount of a strong base; wherein the equivalent ratio of the substituted phenol to formaldehyde or source thereof is 1:1 to 1:4; whereby the saligenin derivative is formed such that X is at least in part —CHO and such —CHO groups comprise at least 10% of the X and Y groups.
REFERENCES:
patent: 2250188 (1941-07-01), Wilson
patent: 2647873 (1953-08-01), Matthews et al.
patent: 3256183 (1966-06-01), Greenwald
patent: 4053428 (1977-10-01), Pindar et al.
patent: 4701354 (1987-10-01), Kitamura et al.
patent: 4916031 (1990-04-01), Kitamura et al.
patent: 5240624 (1993-08-01), Koch
patent: 5259967 (1993-11-01), Ripple
patent: 5371140 (1994-12-01), Parks
patent: 5378791 (1995-01-01), Lancaster et al.
patent: 5516441 (1996-05-01), Denis
patent: 5916851 (1999-06-01), Hosonuma et al.
patent: 6103672 (2000-08-01), Dunn et al.
Abraham William D.
Adams Paul E.
Carrick Virginia A.
Cowling Susan V
Denis Richard A.
Esposito Michael F.
Howard Jacqueline V.
Shold David M.
The Lubrizol Corporation
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