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Novel polyols derived from a vegetable oil using an oxidation processRelated Patent Categories: Synthetic Resins Or Natural Rubbers -- Part Of The Class 520 Series, Polymer Derived From Nitrile, Conjugated Diene And Aromatic Co-monomers, , From Reactant Having At Least One -n=c=x Group (wherein X Is A Chalcogen Atom) As Well As Precursors Thereof, E.g., Blocked Isocyanate, Etc.Novel polyols derived from a vegetable oil using an oxidation process description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20070173626, Novel polyols derived from a vegetable oil using an oxidation process. Brief Patent Description - Full Patent Description - Patent Application Claims
CROSS-REFERENCE TO RELATED APPLICATION [0001] This application claims priority to and the benefit of U.S. Provisional Patent Application No. 60/658,230, filed on Mar. 3, 2005, entitled NOVEL POLYOLS DERIVED FROM A VEGETABLE OIL USING AN OXIDATION PROCESS, the disclosure of which is hereby incorporated by reference in its entirety. BACKGROUND OF THE INVENTION [0002] Because of their widely ranging mechanical properties and their ability to be relatively easily machined and formed, polyurethane materials, such as urethane elastomers and foams, have found wide use in a multitude of industrial and consumer applications. [0003] The production of urethane polymers is well known in the art. Urethanes are formed when isocyanate (NCO) groups react with hydroxyl (OH) groups. The most common method of urethane production is via the reaction of a petroleum-derived-polyol and an isocyanate, which forms the backbone urethane group. Polyester polyols and polyether polyols are the most common polyols derived from petroleum used in urethane production. Polyols are polyhydric alcohols, i.e., alcohols that contain two or more hydroxyl groups. [0004] Sole use of polyols derived from petrochemicals such as polyester or polyether polyols in forming urethane products such as elastomers and foams is disadvantageous for a variety of reasons. Petrochemicals are ultimately derived from petroleum. Accordingly, the petrochemicals are a non-renewable resource. The production of a petroleum-derived polyol requires a great deal of energy, as oil must be drilled, extracted from the ground, transported to refineries, refined, and otherwise processed to yield the polyol. These efforts add to the cost of polyols and to the disadvantageous environmental effects of its production. Also, the price of petroleum-derived polyols tends to be somewhat unpredictable as it tends to fluctuate based on the fluctuating price of petroleum. [0005] Also, as the consuming public becomes increasingly aware of environmental issues, there are distinct marketing disadvantages to petrochemical based products. Consumer demand for "greener" products continues to grow. As a result, it would be most advantageous to replace all or at least some of the polyester or polyether polyols, as used in the production of urethane polymers, with a more versatile, renewable, less costly, and more environmentally friendly component, such as vegetable oil-derived polyols. [0006] One difficulty with the use of vegetable oil-derived polyols to produce a urethane product is that conventional methods of preparing polyols from vegetable oils, such as soybean oils, do not produce polyols having a significant content of hydroxyl groups. Accordingly, it would be advantageous to develop a method to produce vegetable oil-based polyols having increased reactive hydroxyl groups over conventional polyols derived from a vegetable oil such as blown vegetable oil. [0007] Another difficulty with the use of vegetable oil-derived polyols to produce a urethane product is higher than desired residual acid values of the polyol, especially in blown soybean oil polyols (typical blown soybean oil-derived polyol, the residual acid value of a soybean oil-derived polyol ranges from about 5.4 mg KOH/gram to about 7.4 mg KOH/gram). Generally, in the production of urethane elastomers and foams, the residual acid present in vegetable oil-derived polyols retards isocyanate activity by interfering with the isocyanate/alcohol reaction. Also, where the catalyst used to produce urethane polymers is an amine, it is believed that the residual acid can neutralize the amine, making the catalyst less effective. Accordingly, it would be advantageous to develop a method to neutralize the residual acid of the polyol to form reactive hydroxy (OH) groups while not adversely impacting performance of the polyol. A lower acid vegetable oil-derived polyol would be desirable because the lower acid value would improve the performance of polyols in the production of urethane polymer, lower polyurethane catalyst requirements, and improve urethane physical properties due to improved polymer network formation. Accordingly, a significant need exists for low acid, higher functional polyols derived from vegetable oil, especially polyols derived from soybean oil, typically blown soybean oil, and a method for producing such lower acid, higher functional polyols. SUMMARY OF THE INVENTION [0008] One embodiment of the present invention generally relates to a method for making polyols derived from vegetable oil where the polyols have increased hydroxyl functionality where a vegetable oil, typically soybean oil, is reacted with an oxidizing agent in the presence of an organometallic catalyst and the resulting higher functional polyols derived from vegetable oil produced by the process. [0009] Another embodiment of the present invention generally relates to lower acid, higher functionality polyols derived from a vegetable oil and a new method for decreasing the acid value of a polyol by reacting a vegetable oil-derived polyol having increased functionality formed by reacting the vegetable oil, typically a blown soybean oil, with an oxidizing agent in the presence of an organometallic (tetra amido macrocylic ligand) catalyst with an epoxide component in the presence of a Lewis base catalyst. [0010] The present invention further generally relates to the use of (1) the higher functional polyol derived from a vegetable oil, typically a refined and bleached vegetable oil, formed by reacting an oxidizing agent with the vegetable oil in the presence of an organometallic catalyst and/or (2) the lower acid, higher functional vegetable oil-derived polyols as the polyol or one of various polyols and/or as a component of a prepolymer in the production of urethane material, including foams and elastomers. The polyols may be one of the components of the B-side, which can be reacted with an A-side that typically includes a prepolymer (traditional petroleum-derived prepolymer or a prepolymer incorporating a polyol at least partially derived from a vegetable including a lower acid vegetable oil-derived polyol) or an isocyanate. [0011] Another embodiment of the present invention includes the use of the higher functional, typically also lower acid polyols derived from vegetable oil as one of the B-side components (other polyols derived from petroleum may also be used in combination with the higher functional polyols of the present invention as polyol components of the B-side) that is reacted with an A-side that includes an isocyanate and/or a prepolymer, such as the prepolymers discussed above, to form a urethane material. The urethane materials can be used as a precoat and for a backing material for carpet, building composites, insulation, spray foam insulation, other urethane applications such as those requiring use of impingement mix spray guns, urethane/urea hybrid elastomers, vehicle bed liners, flexible foams (furniture foams, vehicle component foams), integral skin foams, rigid spray foams, rigid pour-in-place foams, coatings, adhesives, sealants, filament winding, and other urethane composites, foams, elastomers, resins, and reaction injection molding (RIM) applications. DETAILED DESCRIPTION OF PREFERRED EMBODIMENT [0012] Applicant has surprisingly discovered that oxidation of a vegetable oil, most typically soybean oil, in the presence of an organometallic catalyst, typically a TAML.RTM. (tetra amido macrocyclic ligand) catalyst, results in a vegetable oil-derived polyol having increased hydroxyl group functionality. A method for producing vegetable oil-derived polyols with increased functionality having lower acid values has also been developed. [0013] The method for making a vegetable oil-based polyol with increased functionality generally includes reacting a vegetable oil, typically soybean oil, more typically a refined, bleached soybean oil, with an oxidizing agent in the presence of an organometallic (tetra amido macrocyclic ligand) oxidation catalyst. Generally, the oxidation reaction occurs at elevated temperatures of from about 95.degree. C. to about 150.degree. C., more typically from about 95.degree. C. to about 110.degree. C., and most typically about 95.degree. C. However, it is presently believed that the oxidation reaction may function at temperatures of about 50.degree. C. or greater. This oxidation process yields a polyol with a hydroxyl value ranging from about 56 mg KOH/gram polyol to about 220 mg KOH/gram polyol. More typically, this oxidation process yields a polyol with a hydroxyl value ranging from about 112 mg KOH/gram of polyol to about 220 mg KOH/gram polyl. Oxidation Reaction [0014] In the oxidation reaction of one embodiment of the present invention, the oxidizing agent is typically a chemical which can act as an electron receptor or is a substance in an oxidation-reduction reaction that gains electrons and whose oxidation number is reduced. Typically, hydrogen peroxide or air and most typically hydrogen peroxide is utilized. However, it is presently believed that oxidizing agents can include all organic peroxides. Typically, where the oxidizing agent is air, dried air is preferably introduced at a rate of about 300 cubic feet per minute (CFM) for the volume of oil used. Where the oxidizing agent is hydrogen peroxide, a solution of from about 35% to about 50% hydrogen peroxide is preferably used. A higher concentration of hydrogen peroxide is generally preferred in order to maximize contribution to the reaction of the oxidizing agent and for completion of the reaction. Preferably, the hydrogen peroxide solution is utilized in amounts ranging from about 10% by weight to about 50% by weight of the reaction material. [0015] Typically, the polyol is a polyol at least partially derived from a vegetable oil, typically a soybean oil, a rapeseed oil, a palm oil, a safflower oil, a sunflower oil, a corn oil, a linseed oil, a tall oil, a toung oil, a canola oil, or a cottonseed oil, more typically a refined, bleached soybean oil, and most typically a refined, bleached soybean oil produced according to the process disclosed in U.S. Pat. Nos. 6,476,244 and 6,759,542, the disclosures of which are incorporated by reference in their entirety. [0016] The vegetable oil-derived polyol, typically a polyol derived from soybean oil, is oxidized in the presence of an organometallic catalyst, typically a TAML.RTM. (tetra amido macrocyclic ligand) catalyst, most typically Fe-TAML.RTM. (iron tetra amido macrocyclic ligand) catalyst. Tetra amido macrocyclic ligand is an environmentally friendly catalyst that causes an oxygen component to work faster and more safely. Specifically, where the oxidizing agent is hydrogen peroxide, the tetra amido macrocyclic ligand catalyst forms activated peroxides that are very reactive, but more selective than free radicals formed during the normal decomposition of hydrogen peroxide. The structure of a tetra amido macrocyclic ligand catalyst is shown in FIG. 1. It is currently believed that an inorganic metal tetra amido macrocyclic ligand activated peroxide complex, typically one based on an iron tetra amido macrocyclic ligand, associates with double bonds on the soybean oil to form hydroxyl groups at the available vinylic sites of the vegetable oil. In the oxidation reaction of one embodiment of the present invention, the amount of the tetra amido macrocyclic ligand catalyst used is typically from about 0.2 ppm to about 200 ppm of catalyst used in the reaction, preferably from about 0.2 to about 2.0 ppm, and most preferably about 0.2. However, it is presently believed that the amount of tetra amido macrocyclic ligand catalyst may be 0.01 ppm or greater. [0017] Applicants have surprisingly discovered that oxidizing a vegetable oil, most typically a soybean oil, in the presence of an organometallic catalyst, typically a tetra amido macrocyclic ligand catalyst, most typically an Fe-- (tetra amido macrocyclic ligand catalyst), results in a vegetable oil-derived polyol having increased hydroxyl group functionality of about 56 mg KOH/gram polyol to about 220 mg KOH/gram polyol, more typically of greater than 85 mg KOH/gram polyol as compared to vegetable oil oxidized by blowing processes, which typically yields a polyol with a hydroxyl value ranging from about 56 mg KOH/gram polyol to about 80 mg KOH/gram polyol. [0018] The following examples demonstrate the oxidation of a vegetable oil, typically soybean oil, in the presence of a tetra amido macrocyclic ligand catalyst to form a vegetable oil-derived polyol having increased hydroxyl functionality. [0019] The following general experimental procedure and sample analysis was used for all example oxidation reactions discussed below. In a multi-neck reactor flask equipped with an agitator blade on a stir shaft connected to a stir motor, a quantity of refined, bleached soybean oil was heated. One neck of the flask was equipped with a 300 mm vigreaux column packed with glass beads beneath a water-cooled side-arm condenser so that distillate could be collected and vacuum distillation could be performed at the end of reaction if desired. A temperature probe and nitrogen inlet were present in the flask. The soybean oil was heated to a desired reaction temperature, typically a temperature of from about 95.degree. C. to about 130.degree. C., before adding the tetra amido macrocyclic ligand catalyst. In air oxidation experiments, dried air was incorporated into the reaction mixture through a stainless steel sparger tube at a rate equivalent to 300 cubic feet per minute for the volume of oil used. In hydrogen peroxide oxidation experiments, the peroxide solution was added in increments specified in each reaction. Continue reading about Novel polyols derived from a vegetable oil using an oxidation process... Full patent description for Novel polyols derived from a vegetable oil using an oxidation process Brief Patent Description - Full Patent Description - Patent Application Claims Click on the above for other options relating to this Novel polyols derived from a vegetable oil using an oxidation process patent application. ###  How KEYWORD MONITOR works... a FREE service from FreshPatents1. Sign up (takes 30 seconds). 2. Fill in the keywords to be monitored. 3. Each week you receive an email with patent applications related to your keywords. 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