CONTEXT

Natural vegetable oils (triglycerides and fatty acid methyl esters) have recently attracted renewed attention as raw materials for the preparation of bio-sourced polymers, appropriate to a multitude of applications.

For example, polyurethanes (PURs) could be prepared by reacting a polyol and an isocyanate. These materials

occupy an important position in the world market of high performance synthetic polymers. PURs have a world production of 14 Mt (in 2006) and are the sixth most widely sold plastic in the world,after HDPE, LDPE, PP, PVC and LLDPE, accounting for approximately 6% of total consumption.

TECHNICAL DESCRIPTION

This invention describes a new three steps method to prepare polyols from mono esters of vegetable oils or triglycerides. The first step consists in a transesterification of the methylic esters then the second step an epoxidation of the double bond and the last step is an opening of the epoxyde ring with an alcohol.

This invention provide access to new synthons , mono esters or diesters, at least bifunctionals (polyols) and having well defined structure.

For example, the inventors have used a variety of sunflower oil with high oleic acid content. The various methyl esters of sunflower oïl have been separated by fractional distillation. Methyl esters of oleic acid of high purity have been obtained. Starting from this precursor it is then possible to provide a selected number of hydroxyl groups and thus to control the functionality of this ‘building block’ monomer. A well-defined structure of

monomers is essential to the development of polymeric materials with properties controlled and reproducible. As the desired polymers should be  linear, the inventors have for example tried to create at least difunctional monomers (di-OH) from oleic sunflower methyl esters.

BENEFITS

It is possible to obtain from vegetables oils well defined symetrical diols having two primary hydroxyl functions and assymetrical diols with a primary hydroxyl functions and a secondary hydroxyl function

INDUSTRIAL APPLICATIONS

Polyurethanes have been synthetised by bulk polymerization of these polyols with isophorone diisocyanate (IPDI). When reacting with isocyanates to form polyurethanes  these compounds could be used as flexible foams, rigid foams, elastomers, fibers, molding compositions, surface coatings and adhesives

But these diols can also be used to synthetise polymers like polyester, polyethers or polycarbonates.

DEVELOPMENT STAGE

Products have shown good properties in adhesive and cosmetics applications. The pilot scale (2kg) has been achieved. The scale up is Under developpement (50kg)…

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