Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Compound of indeterminate structure – prepared by reacting a...
Reexamination Certificate
2002-06-07
2004-03-02
McAvoy, Ellen M. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Compound of indeterminate structure, prepared by reacting a...
C508S405000, C508S410000, C508S412000, C508S452000, C252S391000, C252S395000
Reexamination Certificate
active
06699822
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to sulfated dicarboxylic acids, amine salts thereof, or inorganic salts thereof, their use as corrosion-inhibiting additives in oil-field drilling applications and in metalworking applications, their use as emulsifiers in metalworking applications, and their use as boundary lubricity additives in metalworking applications.
BACKGROUND
Liquid media present in various mechanical systems, such as hydrocarbon-containing liquids in internal combustion engines, pipelines, or storage tanks, may be very corrosive to metal parts that make up the systems. Additionally, because moisture or liquid water is almost always present as contamination from some source in such systems, rusting due to the presence of water can often pose a problem. Moreover, with changing temperatures over the course of a day, vapor present in a tank or pipeline may expand or contract. When it contracts, ambient air may be drawn into the tank or pipeline (and subsequently into any connected system, such as an engine), and any moisture contained in that air then may condense inside the tank, pipeline, or engine. A considerable volume of water may be introduced into a tank during an extended storage period, especially when located in a humid environment. Additional dangers potentially resulting from rusting during storage lie in the damage to costly equipment, contamination of the fuel due to the presence of particles of iron oxide (i.e., from the rust or corrosion) that may scale off the walls of a tank or pipeline, and contamination of the environment because of a leak resulting from the corrosion of the walls of a tank or pipeline. Thus, inhibiting corrosion or rusting of metal surfaces is an important factor in maintaining such systems in proper and efficient working condition, in assuring longevity of the systems, and in protecting the environment.
As is known, fatty acids, and in particular, polymerized fatty acids known as “dimer acids,” may be used as corrosion inhibitors in numerous systems. Examples of dimer acids used as corrosion inhibitors are provided in U.S. Pat. No. 2,482,761 to Goebel, U.S. Pat. No. 2,631,979 to McKermott, and U.S. Pat. No. 2,632,695 to Landis. These patents discuss polymerized diunsaturated monocarboxylic acids, e.g., dilinoleic acid and the dimeric acids obtained by the distillation of castor oil in the presence of sodium hydroxide, as being particularly suitable. Other sources of dimeric acids include tall oil fatty acids, such as oleic or linoleic acids.
Various dicarboxylic acids also are known in the art for various applications. For example, U.S. Pat. No. 3,753,968 (to Ward) discloses the preparation of a C
21
dicarboxylic acid that may be used as a plasticizer or an epoxy curing agent. U.S. Pat. No. 3,842,119 (to Bills) describes a hydroxypropane sulfonated adduct of a soap of the dicarboxylic acid of Ward's '968 Patent. This adduct is used as a lime dispersant.
U.S. Pat. No. 3,981,682 to Ward describes another use of the dicarboxylic acid according to the '968 Patent. This patent describes the use of the dicarboxylic acid, an alkali metal salt thereof, a mono or bis-alkanolamide derivative thereof, or an alkali metal salt of the alkanolamide derivative as a corrosion inhibitor to inhibit rust formation on metallic surfaces contact by petroleum hydrocarbons and aqueous media.
The DuVernet patents, U.S. Pat. Nos. 4,476,055 and 4,514,335, describe hemi- and bis-isethionate products prepared by reacting an alkali metal, ammonium or substituted ammonium 2-hydroxyethane sulfonate with a C
21
dicarboxylic acid. DuVernet discloses the use of these products as detergents for cleaning clay-soiled fabrics and notes their use as surfactants.
U.S. Pat. No. 4,614,600 to Schilling describes using an adduct of a polyamine, such as a di- or tri-ethyleneamine, and the dicarboxylic acid of the '968 Patent, as an anti-corrosive composition in well-drilling operations. Another Schilling patent, U.S. Pat. No. 4,494,992, describes amphoteric emulsifiers for making bituminous emulsions. The emulsifiers include a modified reaction product of a polycarboxylic acid.
The Woodward patents, U.S. Pat. Nos. 4,956,106 and 5,008,039, describe a low-foaming, rust-inhibiting composition including a blend of a dicarboxylic acid product according to the '968 Patent (as a rust inhibitor) and a vegetable oil adduct that is a triglyceride addition product with the dicarboxylic acid (as a foam inhibitor).
Lege, U.S. Pat. No. 4,571,309, describes emulsifiers prepared by reacting an ammonium or substituted ammonium methyl isethionate alcohol with a C
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-cycloaliphatic tricarboxylic acid.
Each of the above-identified patents is entirely incorporated herein by reference.
SUMMARY
In one aspect, this invention relates to certain sulfated cyclic dicarboxylic acids, their amine salts, and their inorganic salts. Compositions according to some examples of this invention may be obtainable by reacting sulfuric acid and at least one reactant selected from the group consisting of:
wherein, in these formulae:
(a) x and y each independently represents an integer from 3 to 9, wherein x and y together equal 12, and (b) Z represents a moiety selected from the group consisting of hydrogen and COOH, wherein at least one Z is hydrogen and one Z is COOH. Any suitable source of sulfuric acid can be used in the reaction without departing from this invention.
In another aspect, this invention relates to sulfated cyclic dicarboxylic acids and amine salts and inorganic salts thereof according to the formula:
wherein:
(a) x and y each independently represents an integer from 3 to 9, wherein x and y together equal 12, (b) Z represents a moiety selected from the group consisting of hydrogen and COOM, wherein at least one Z is hydrogen and one Z is COOM, (c) W represents a member selected from the group consisting of hydrogen and —O—SO
3
M, wherein at least one W represents —O—SO
3
M, and (d) M represents a member selected from the group consisting of hydrogen, an inorganic ion, or an amine radical, wherein each M may be the same or different. The reaction between sulfuric acid and the cyclic dicarboxylic acid or lactone thereof as described in the preceding paragraph may result, at least in part, in a composition containing a sulfated cyclic dicarboxylic acid as illustrated in this formula.
While any suitable amine may be used to form an amine salt yielding an amine radical as substituent “M” without departing from this invention, one suitable class of amines includes alkanolamines, such as triethanolamines, diglycolamines, monoethanolamines, and isopropanolamines. Likewise, while any suitable inorganic base may be used to form an inorganic salt yielding an inorganic ion as substituent “M” without departing from this invention, one suitable class of inorganic bases includes the alkali metal hydroxides, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide. Ammonium hydroxide also may be used as the inorganic base without departing from the invention.
Other aspects of this invention relate to the use of the sulfated cyclic dicarboxylic acid-containing compositions according to the invention as additives for inhibiting corrosion or enhancing lubricity of a material. As one example, the sulfated cyclic dicarboxylic acid (or its amine salt or its inorganic salt) may be used as an additive in hydrocarbon production, storage, and/or transport to inhibit corrosion of metal surfaces contacted by the hydrocarbon (such as a wall of a pipeline or a storage tank). When used as such, the additive may be present in the hydrocarbon in any suitable corrosion inhibiting amount, usually less than 5%, by weight, based on a total weight of the combined hydrocarbon and additive, and preferably in an amount of less than 3%, by weight, or even less than 1%, by weight. When used as a corrosion inhibitor, the corrosion-inhibiting additive and the corrosive material being treated may contact the metal surface (either independently or concurrently), and the corrosion-inhibiti
Bruner Michael C.
Hurd Phillip W.
Netzel Arnold
Banner & Witcoff , Ltd.
Georgia-Pacific Resin, Inc.
McAvoy Ellen M.
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