Novel polyols derived from a vegetable oil using an oxidation process

Abstract

A method for producing a vegetable oil-derived polyol having increased hydroxyl functionality by reacting a vegetable oil with an oxidizing agent in the presence of an organometallic catalyst is provided. The resulting higher functionality polyols derived from vegetable oil produced by the process are also provided. Also provided is a method for decreasing the acid value of a vegetable oil-derived polyol by reacting the vegetable oil-derived polyol with an epoxide component in the presence of a Lewis base catalyst. Urethane products produced using higher functional vegetable oil-derived polyols and / or lower acid vegetable oil-derived polyols are also provided.

Description

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 polyol...

AI Technical Summary

Problems solved by technology

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.

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.

Also, as the consuming public becomes increasingly aware of environmental issues, there are distinct marketing disadvantages to petrochemical based products.

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.

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).

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.

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