Colloid systems and wetting agents; subcombinations thereof; pro – Continuous liquid or supercritical phase: colloid systems;... – Aqueous continuous liquid phase and discontinuous phase...
Reexamination Certificate
2002-03-21
2004-03-16
Metzmaier, Daniel S. (Department: 1712)
Colloid systems and wetting agents; subcombinations thereof; pro
Continuous liquid or supercritical phase: colloid systems;...
Aqueous continuous liquid phase and discontinuous phase...
C516S204000, C554S149000, C424S059000, C424S070310, C424S074000, C514S785000, C514S787000
Reexamination Certificate
active
06706768
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel alkoxylated monoesters, their uses, and methods of manufacture thereof. More specifically, the present invention is related to ethoxylated monoesters, propoxylated monoesters and ethoxylated/propoxylated monoesters produced from partially or wholly trans-free double-bonded jojoba ester products.
BACKGROUND
Natural products and their derivatives are increasingly favored in the cosmetics industry since consumers have become more environmentally sensitive. Further, consumers have recognized the value of many unique properties displayed by natural products and their derivatives.
One common method of producing natural products for the cosmetic industry is to extract an oil or wax from the seed of a plant. Oils and waxes are a group of organic substances that form an important and useful part of the cosmetic and other industries. Generally, waxes are solid and oils are liquid at ordinary room temperatures. However, some tropical products, which are liquids in their sites of origin, become solids in cooler climates, often retain the name originally given, e.g., palm oil and coconut oil. Waxes and oils are derived from both plant and animal sources.
Chemically most fats and oils are either simple or mixed glyceryl esters of organic acids belonging to the fatty-acid series (triglycerides). Triglycerides are esters formed from glycerol and three fatty acids that may be identical or different from each other. In a simple triglyceride such as tripalmitin or tristearin, all three fatty-acid groups are identical. In a mixed triglyceride, two or even three different fatty-acid groups are present. Most oils and waxes contain mixed triglycerides.
Waxes are often found as trace components of triglyceride oils or can be extracted in a more pure form from certain botanical and animal sources. Sunflower and corn oils contain natural waxes, while jojoba, carnauba and candelillia are examples of waxes found naturally in a more pure form. Beeswax and lanolin are examples of natural waxes of insect and animal origin. These example waxes range from the liquid, unsaturated jojoba oil to the almost completely saturated sunflower wax.
In order to control, or modify, various properties, such as solubility or melting point, of oils and waxes, certain modifications can be introduced into the triglyceride and/or wax ester structure. One such modification is the introduction of ethylene oxide (ETO) and/or propylene oxide (PO) units to the hydroxyl function of a hydrolyzed triglyceride or wax ester. It has been found that by controlling the number of units ETO or PO added, various properties such as solubility and melting point can be adjusted in the oil or wax. Generally, it has been found that compounds become more water soluble as the level of ethoxylation increases, but become more alcohol soluble, more oil soluble and more fluid as the level of propoxylation increases. Compounds that are ethoxylated, as well as propoxylated, acquire both water and alcohol solubility. Because ethoxylation also raises the melting point of materials, ethoxylates vary in form, depending on the level of ethoxylation. For instance, when a liquid starting material is ethoxylated with approximately 15 moles of ethylene oxide, it may become solid or semi solid at room temperature. Propoxylates, however, are more often liquids because they contain branched polyoxypropylene chains. Branching tends to keep materials fluid.
Another method of altering the melting points of oils and waxes is to add hydrogen to points of unsaturation within the oil or wax molecule. The addition of hydrogen is typically accomplished under several atmospheres of pressure at elevated temperatures and in the presence of metal catalysts, such as nickel or palladium. This hydrogenation process can be continued until all points of unsaturation within the oil or wax molecule are saturated with hydrogen, or the reaction can be stopped at some point short of achieving a fully saturated oil or wax. The melting point of the oil or wax generally increases as a linear function of the amount of hydrogen that has been added. A hydrogenation reaction is said to yield “partially hydrogenated” material when stopped short of achieving a “fully saturated” oil or wax. The melting point of these “partially hydrogenated” materials is less than the melting point of the “fully saturated” material and higher than the melting point of the starting oil or wax.
Although partial hydrogenation is a means of adjusting the melting point of an oil or wax, this partial hydrogenation process results in the formation of unwanted “trans” isomers. These trans isomers have been shown to be harmful in human nutrition and have an inhibitory effect on the natural metabolic pathway whereby prostaglandins are created in the skin.
While alkoxylation is a process whereby the melting points and solubility of various oils and waxes can be modified, there is a need to expand the range of melting points of alkoxylated materials. Partial hydrogenation to achieve a higher melting point is not desirable because of the formation of unwanted trans isomers. There is a need to have a broad range of melting points of alkoxylated oils and waxes with elevated melting points that are free or substantially free of trans isomers created through partial hydrogenation.
SUMMARY OF INVENTION
It is an object of the present invention to provide a composition that is useful for cosmetic and other applications.
It is another object of the present invention to provide a substantially trans carbon-carbon double bond free composition comprising an alkoxylated wax ester, where the wax ester is substantially trans carbon-carbon double bond free prior to being alkoxylated.
It is yet another object of the present invention to provide the composition above wherein the alkoxylate is prepared using ethylene oxide.
It is still yet another object of the present invention to provide the composition above wherein the alkoxylate is prepared using propylene oxide.
It is a further object of the present invention to provide the composition above wherein the alkoxylate is prepared using a mixture of ethylene oxide and propylene oxide.
It is yet a further object of the present invention to provide the composition above where the alkoxylation is roughly 150 mol equivalents.
It is still yet a further object of the present invention to provide a substantially trans carbon-carbon double bond free composition comprising an alkoxylated wax ester, where the wax ester is substantially trans carbon-carbon double bond free prior to being alkoxylated and where the wax ester is a partially saturated wax ester, the wax ester being substantially trans carbon-carbon double bond free prior to partial saturation.
It is another object of the present invention to provide the composition above wherein the alkoxylate of the trans free wax ester is prepared using ethylene oxide.
It is still another object of the present invention to provide the composition above wherein the alkoxylate is prepared using propylene oxide.
It is yet another object of the present invention to provide the composition above wherein the alkoxylate is prepared using a mixture of ethylene oxide and propylene oxide.
It is still yet another object of the present invention to provide the composition above where the alkoxylation is roughly 150 mol equivalents.
It is a further object of the present invention to provide a substantially trans carbon-carbon double bond free composition comprising an alkoxylated wax ester, where the wax ester is substantially trans carbon-carbon double bond free prior to being alkoxylated where the wax ester that is substantially trans carbon-carbon double bond free prior to being alkoxylated is a fully saturated wax ester, the saturated wax ester being substantially trans carbon-carbon double bond free prior to partial saturation.
It is yet a further object of the present invention to provide the composition above wherein the alkoxylate is prepared using ethylene oxide.
It is still a further object of the p
Brown James H.
Hill John C.
Kleiman Robert
International Flora Technologies Ltd.
Metzmaier Daniel S.
The Halvorson Law Firm
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