Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Organic -co- compound
Reexamination Certificate
1999-10-29
2001-08-07
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
C508S491000, C554S108000, C554S109000, C554S110000, C554S114000
Reexamination Certificate
active
06271185
ABSTRACT:
TECHNICAL FIELD
The invention relates to a method for modifying triacylglycerol oils to improve their water dispersibility.
BACKGROUND OF THE INVENTION
Oils used in metalworking typically contain mono- and diethanolamine based fatty acid amides, which are suspected carcinogens, and/or petroleum based hydrocarbons, which can damage the environment. Plant oils are an environmentally friendly alternative to such products, and are based on renewable natural resources. The major components of plant oils are triacylglycerols (TAGs), which contain three fatty acid chains esterified to a glycerol moiety. The polar glycerol regions and non-polar hydrocarbon regions of TAGs are thought to align at the boundaries of metal surfaces and provide boundary lubrication, and thus have better lubricant properties than petroleum hydrocarbons. The negligible water-solubility of plants oils, however, limits their use for water-based applications such as metalworking.
SUMMARY OF THE INVENTION
The invention is based on the discovery that transesterification of triethanolamine (TEA) or ethoxylated TEA and a triacylglycerol (TAG) oil improves the water dispersability of the TAG oil. The resulting product can be used for a variety of industrial applications, including, for example, metalworking. Such oils are less toxic to people using them than typical metalworking fluids, as they do not contain mono- or diethanolamine based fatty acid amides, which are considered to be harmful to humans.
In one aspect, the invention features a method for improving water dispersability of a vegetable oil. The method includes transesterifying the vegetable oil with triethanolamine or ethoxylated triethanolamine to form partial esters. The vegetable oil can be, for example, corn oil, rapeseed oil, soybean oil, or sunflower oil. Canola oil is a useful rapeseed oil. Suitable vegetable oils can have a monounsaturated fatty acid content of at least 70%, e.g., about 70% to about 95%. The method further can include quaternizing the transesterified oil.
The invention also features an oil including compounds of formula A and formula B:
wherein R
1
-R
6
are a hydroxyl moiety or
wherein Y is an aliphatic hydrocarbyl moiety having three to 23 carbons atoms (e.g., 11 to 23 carbon atoms), wherein at least 50 weight % of the compounds of formula A and B contain a hydroxyl moiety and at least 50 weight % of the compounds of formula A and B contain
and wherein X is 0 or 1. In some embodiments, at least 70% of the aliphatic hydrocarbyl moieties are monounsaturated. Aliphatic hydrocarbyl moieties having 11 to 23 carbon atoms can be selected from the group consisting of an oleoyl moiety, eicosenoyl moiety, and an eracoyl moiety. Two of R
1
, R
2
, and R
3
can be
or two of R
4
, R
5
, and R
6
can be
Compound of formula A can be about 20 to about 70%, by weight, of the oil.
The oil further can include one or more additives selected from the group consisting of an antioxidant additive, an antiwear additive, an antirust additive, an antifoam additive, and a biocidal additive.
In another aspect, the invention features a cutting fluid concentrate containing an oil of the invention, a surfactant, and one or more additives selected from the group consisting of a biocidal agent, a corrosion inhibitor, an extreme pressure additive, an antiwear additive, an antirust additive, and an antifoam additive. The surfactant can be about 1 to about 15 weight % of the cutting fluid concentrate and the additives can be a maximum of about 10 weight % of the cutting fluid concentrate.
The invention also features a method of producing a transesterified oil. The method includes transesterifying a triacylglycerol oil and triethanolamine or ethoxylated triethanolamine to produce the sesterified oil, wherein the transesterified oil comprises compounds of formula A and formula B described above. The method further can include quaternizing the compound having formula B to form a quaternary ammonium salt. The triacylglycerol oil can be a vegetable oil having, for example, a monounsaturated fatty acid content of at least about 50% or at least 70% (e.g, 70% to about 95%).
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used to practice the invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. In case of conflict, the present specification, including definitions, will control. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.
Other features and advantages of the invention will be apparent from the following detailed description, and from the claims.
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Kodali Dharma
Nivens Scott C.
Cargill Incorporated
Fish & Richardson P.C.
McAvoy Ellen M.
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