Fuel and related compositions – Liquid fuels – Containing organic -c
Reexamination Certificate
1999-12-07
2001-03-20
Howard, Jacqueline V. (Department: 1764)
Fuel and related compositions
Liquid fuels
Containing organic -c
Reexamination Certificate
active
06203585
ABSTRACT:
TECHNICAL FIELD
The present invention relates to heavy cut methyl ester compositions containing copolymer additives which result in lower pour points as compared to methyl ester compositions without such copolymer additives. Specifically, heavy cut methyl ester compositions containing alkyl methacrylate copolymers are provided that result in lower pour points to solve problems that plague current compositions in the metalworking lubricant, agricultural adjuvant, drilling mud, and biodiesel fuel markets.
BACKGROUND OF THE INVENTION
Heavy cut methyl esters of vegetable oils and animal fats, as defined hereinafter, are useful in a variety of contexts. In particular, heavy cut methyl esters have been used as lubricants in the metalworking industry. See, e.g., Williams et al., U.S. Pat. No. 5,716,917, issued Feb. 10, 1998. Heavy cut methyl esters are preferred over other types of lubricants, such as mineral oils, due to their lower cost, lower toxicity, and environmental friendliness. However, a disadvantage for using heavy cut methyl esters as metalworking lubricants relates to their relatively high pour points, which are typically at or above the freezing point of water. This disadvantage has prevented these low cost, low toxicity, and environmentally friendly, heavy cut methyl esters from becoming more widely used as metalworking lubricants. It has been desired to discover a way to lower the pour points of these heavy cut methyl esters so that they can be more effectively used as metalworking lubricants.
Heavy cut methyl esters of vegetable oils and animal fats are also particularly useful in the agricultural adjuvant market, in which they are used as carriers for the active ingredients in pesticides. See, e.g., Synek, U.S. Pat. No. 5,612,048, issued Mar. 18, 1997; Wessling et al., U.S. Pat. No. 5,508,035, issued Apr. 16, 1996; Bencsits, U.S. Pat. No. 5,589,181, issued Dec. 31, 1996. Such pesticides are often stored outside in large drums for future agricultural use. However, in colder climates, such storage can result in the pesticides becoming frozen, which then requires a great amount of effort to thaw the pesticides before use. While other carriers, such as mineral oils, can be used so that the pesticides do not freeze quite as readily, their cost is prohibitive and their use has raised environmental concerns. Using heavy cut methyl esters as the carrier material in pesticides has economic and environmental benefits. Thus, it has been desired to create heavy cut methyl ester compositions with lower pour points to be used as a carrier in pesticides which will not freeze as readily when stored outside in colder climates.
Heavy cut methyl esters of vegetable oils and animal fats have also been useful as a base for drilling muds and fluids. See, e.g.,
Advances in Drilling Covered at Conference in Southeast Asia
, OIL & GAS JOURNAL, p. 41 (PennWell Publ'g Feb. 1, 1993). Diesel and mineral oils have typically been used as the base for these muds and fluids, however their use has raised environmental concerns. Due to their environmental friendliness, heavy cut methyl esters have been effectively used as a base for drilling muds and fluids. However, heavy cut methyl esters are undesirable for use in drilling muds in colder climates due to their higher pour points.
Heavy cut methyl esters have also been useful as biodiesel fuels. See, e.g., Foglia et al., U.S. Pat. No. 5,713,965, issued Feb. 3, 1998; Demmering et al., U.S. Pat. No. 5,389,113, issued Feb. 14, 1995; Lal, U.S. Pat. No. 5,338,471, issued Aug. 16, 1994. As previously discussed, a disadvantage to using heavy cut methyl esters has been their relatively high pour points, which causes them to solidify in fuel pipes at temperatures at or above the freezing point of water so that they cannot be effectively used as biodiesel fuel under winter conditions in cold climates.
SUMMARY OF THE INVENTION
The present invention relates to the pour point depression of heavy cut methyl esters by the addition of an alkyl methacrylate copolymer. The pour points of such methyl ester compositions can be further depressed by a minimal amount of agitation after the addition of the alkyl methacrylate copolymer. The ability to achieve a lower pour point for heavy cut methyl ester compositions is especially important for the use of methyl esters as metalworking lubricants, as carriers for active ingredients in pesticides which do not freeze as readily upon outdoor storage in cold climates, as a base for drilling muds and fluids, and as biodiesel fuels which do not freeze in fuel pipes at winter temperatures in cold climates.
The present invention encompasses heavy cut methyl ester compositions containing copolymer additives which have lower pour points as compared to methyl ester compositions without such copolymer additives. The compositions of the present invention comprise:
(I) from about 95% to about 99%, by weight of the composition, of a methyl ester, or mixtures thereof, of fatty acids having from about 14 to about 24 carbon atoms; wherein said methyl ester has an iodine value from about 75 to about 125; and
(II) from about 1% to about 5%, by weight of the composition, of a copolymer additive comprising:
(A) from about 25% to about 75%, by weight of the copolymer additive, of a polymer comprising:
(i) from about 70% to about 99.5%, by weight of the polymer, first repeating units, each derived from a C
8
-C
15
alkyl methacrylate monomer; and
(ii) from about 0.5% to about 30%, by weight of the polymer, second repeating units, each derived from a C
16
-C
24
alkyl methacrylate monomer; and
(B) from about 25% to about 75%, by weight of the copolymer additive, of a vegetable oil or polyol ester.
The compositions of the present invention have pour points below about 5° C., preferably below about 0° C., more preferably below about −5° C. Once the compositions of the present invention begin to crystallize, their pour points can be further depressed, by agitation, to temperatures below about 0° C., preferably below about −5° C., more preferably below about −120° C.
The present invention also encompasses processes for making heavy cut methyl ester compositions having depressed pour points and methods of using said compositions.
Unless otherwise noted, all documents cited herein are incorporated by reference.
DETAILED DESCRIPTION OF THE INVENTION
The heavy cut methyl ester compositions of the present invention contain heavy cut methyl esters mixed with alkyl methacrylate copolymer additives, which result in the compositions having pour points which are lower than heavy cut methyl esters without such copolymer additives. The heavy cut methyl ester compositions of the present invention comprise from about 95% to about 99%, preferably from about 96% to about 98.5%, more preferably from about 97% to about 98%, heavy cut methyl esters; and from about 1% to about 5%, preferably from about 1.5% to about 4%, more preferably from about 2% to about 3%, alkyl methacrylate copolymer additive.
Using ASTM Method D97 to measure pour point, the compositions of the present invention exhibit pour points less than about 5° C., preferably less than about 0° C., more preferably less than about −5° C. It has been discovered that, by agitation, the compositions of the present invention can exhibit pour points of less than about 0° C., preferably less than about −5° C., more preferably less than about −12° C. Once the compositions begin to crystallize or solidify, agitation serves to break the initial crystalline structure formation and allows the compositions to attain lower pour points. Such agitation can be accomplished by stirring or shaking the compositions, i.e., with a stirring rod or shaking the mixing vessel. To minimize the amount of agitation required to break the initial crystalline structure formation, the present compositions preferably contain greater than about 2% copolymer additive.
As described hereinafter in Example IV, an oscillatory stress test can be used to determine the amount of force necessary to break the cr
Camp Jason J.
Howard Jacqueline V.
The Procter & Gamble & Company
Turner Frank C.
Zerby Kim W.
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