Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Organic compound containing boron
Reexamination Certificate
1993-06-03
2001-05-08
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
C508S364000, C508S322000
Reexamination Certificate
active
06228818
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to borate esters of hydroxy-containing organophosphorus compounds, and lubricants and aqueous fluids containing borate esters.
INTRODUCTION TO THE INVENTION
Boron-, phosphorus-, and sulfur-containing compositions have been utilized in lubricating compositions as multi-functional additives such as extreme pressure and anti-wear agents.
U.S. Pat. No. 3,031,401 relates to lubricating oil composition containing amine salts of boronated partially esterified thiophosphates. These materials are the reaction product of an oil-soluble primary, secondary or tertiary alkyl, alkenyl, alkylol mono- or diamine and an anhydride prepared by reacting a partially esterified thiophosphoric acid with boric acid, boric oxide or an anhydride of boric acid and an aliphatic monocarboxylic acid.
U.S. Pat. No. 3,213,022 relates to lubricants containing metal phosphorodithioic-epoxide reaction products. These products are the reaction of a metal salt of phosphorodithioic acid and an organic epoxide.
U.S. Pat. No. 3,291,734 relates to boron-, phosphorus- and sulfur-containing additives and methods of making the same. These products were prepared by reacting an alpha-olefin with phosphorus pentasulfide to form an intermediate. The intermediate is then reacted with glycols or mixtures of glycols and alcohols to form a second intermediate, and finally the second intermediate is reacted with glycol borates or precursors thereof, such as a mixture of boric acid and glycol. These additives are useful in lubricating oils.
U.S. Pat. No. 4,368,129 relates to multi-functional lubricant additives which are metal salts of partially borated, partially phosphosulfurized polyols and hydroxy-containing esters. These additives are useful as friction reducing, antioxidant and copper strip passivating additives in lubricating media. The additives may be prepared by first partially phosphosulfurizing a hydroxyl-containing ester by reacting the hydroxyl-containing ester with a phosphosulfur compound such as phosphorus pentasulfide and then reacting the partially phosphosulfurized compound with a metal compound and thereafter borating the metal salt of the partially phosphosulfurized hydroxyl-containing ester.
U.S. Pat. No. 4,529,528 relates to boratedamine-phosphite reaction products and lubricants and fuels containing the same. The products are prepared by reacting a (2-hydroxyethyl)alkylamine or certain higher oxylated members, a dihydrocarbylphosphite in a boron compound. These additives are useful as friction reducers in lubricating compositions.
U.S. Pat. No. 4,536,306 relates to borated phosphorus-containing compounds and lubricant compositions containing the same. The compounds are prepared by reacting a phosphorus oxyhalide, a vicinal diol and a boron compound. These additives are useful in reducing friction in lubricating compositions.
U.S. Pat. No. 4,784,780 relates to lubricant additives comprising mixed hydroxyester or diol/phosphorodithioate-derived borate. The additives are prepared by reacting dialkyl or diaryl phosphorodithioate-derived alcohols and hydrocarbyl diols, hydroxyesters or related polydiols with a boronating agent.
SUMMARY OF THE INVENTION
This invention relates to a borate ester prepared by reacting a hydroxy-containing organophosphorus compound with a borating agent. In one embodiment, these reaction products may be represented by the following formulae alone or in combination:
wherein each R
1
is independently hydrogen, a hydrocarbyl, hydrocarbyloxy or hydrocarbylthio group or both R
1
on the same phosphorus atom taken together form a heterocyclic group each X
1
and X
2
is independently an oxygen or sulfur; and each R
2
is independently a hydrocarbylene group, provided that at least one R
1
is other than hydrogen. These reaction products are useful as lubricant additives for oil-based and water-based functional fluids. These materials act as anti-wear, extreme pressure and friction modifying agents.
DETAILED DESCRIPTION OF THE INVENTION
The term “hydrocarbyl” includes hydrocarbon as well as substantially hydrocarbon groups. Substantially hydrocarbon describes groups which contain non-hydrocarbon substituents which do not alter the predominantly hydrocarbon nature of the group.
Examples of hydrocarbyl groups include the following:
(1) hydrocarbon substituents, that is, aliphatic (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl, cycloalkenyl) substituents, aromatic-, aliphatic- and alicyclic-substituted aromatic substituents and the like as well as cyclic substituents wherein the ring is completed through another portion of the molecule (that is, for example, any two indicated substituents may together form an alicyclic radical);
(2) substituted hydrocarbon substituents, that is, those substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent; those skilled in the art will be aware of such groups (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, sulfoxy, etc.);
(3) hetero substituents, that is, substituents which will, while having a predominantly hydrocarbon character within the context of this invention, contain an atom other than carbon present in a ring or chain otherwise composed of carbon atoms. Suitable heteroatoms will be apparent to those of ordinary skill in the art and include, for example, sulfur, oxygen, nitrogen, phosphorus and such substituents as, e.g., pyridyl, furyl, thienyl, imidazolyl, etc. In general, no more than about 2, preferably no more than one, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group. Typically, there will be no such non-hydrocarbon substituents in the hydrocarbyl group. Therefore, the hydrocarbyl group is purely hydrocarbon.
In one embodiment, the borate esters of the present invention may be represented by one of the following formulae alone or in combination:
wherein each R
1
is independently hydrogen, a hydrocarbyl, a hydrocarbyloxy or a hydrocarbylthio group or both R
1
on the same phosphorus atom taken together form a heterocyclic group; each X
1
and X
2
is independently an oxygen or sulfur; and each R
2
is independently a hydrocarbylene group, provided that when one R
1
is hydrogen, the other R
1
is other than hydrocarbon.
Preferably, each R
1
is independently hydrogen, an alkyl, aryl, alkoxy, aryloxy, alkylthio or arylthio group, with an alkoxy or aryloxy group being more preferred. In one embodiment, each R
1
independently contains from 1, or about 3, to about 30 or about 24, or about 18 carbon atoms. Each R
1
may be independently derived from any of the monohydroxy organic compounds listed below. Examples of R
1
include propyl, propoxy, propylthio, butyl, butoxy, butylthio, amyl, amyloxy, amylthio, hexyl, hexyloxy and hexylthio groups. The above list is meant to include all isomeric arrangements of the above groups. For instance, butyl is meant to include isobutyl, sec-butyl, n-butyl, etc. In a preferred embodiment, one R
1
is a isopropoxy or isobutoxy group and the other R
1
is an amyloxy or a methylamyloxy group.
When R
1
is an aryl, aryloxy or arylthio group, R
1
contains from 6 to about 18 carbon atoms, more preferably 6 to about 10. Examples of aromatic R
1
groups include cresyl, cresyloxy, cresylthio, xylyl, xylyloxy, xylylthio, heptylphenol, and heptylphenolthio groups, preferably cresyl or cresyloxy groups.
X
1
and X
2
are each independently oxygen or sulfur, preferably sulfur. In one embodiment, X
1
or X
2
is sulfur and correspondingly X
2
or X
1
is oxygen. In another embodiment, both X
1
and X
2
are sulfur or both X
1
and X
2
are oxygen. A s described, the organophosphoryl borates of the present invention are prepared by reacting a hydroxy-containing organophosphorus compound with a boron compound. The hydroxy-containing organophosphorus compound is prepared by reacting an organophosphorus acid with an epoxide.
The organophosphorus acids useful in preparing the
Dibiase Stephen A.
Rizvi S. Q. Abbas
Schwind James J.
Esposito Michael F.
Howard Jacqueline V.
The Lubrizol Corporation
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