Thermoset materials derived from epoxidized sucrose esters, a biobased product, have demonstrated excellent performance properties. The implementation of biobased multifunctional carboxylic acids as crosslinkers for these systems could lead to a 100% biobased coating being produced. The primary problem in realizing this system is that multifunctional carboxylic acids have a high degree of hydrogen bonding between molecules, resulting in high melting points and poor solubility in organic systems. A way to overcome these problems is to block the carboxylic acids by reacting them with vinyl ethers. The blocked carboxylic acids have four positive attributes: 1) the reaction to produce them can be performed without the need of a solvent nor an inert atmosphere, 2) the blocked acids are low viscosity liquids that are soluble in organics, 3) the deblocking reaction is thermally activated at moderate temperatures (170 �C), and 4) the vinyl ethers (which are not biobased) are volatile at these deblocking temperatures. Therefore, while the formulation is 92-95% biobased (depending on the multifunctional acid and the vinyl ether used), the final coating produced is 100% biobased. The synthesis of novel vinyl ether blocked carboxylic acids and their use with epoxidized sucrose soyate (ESS) in thermoset systems, which have shown both good surface adhesion and solvent resistance, will be presented. 

Vinyl ether blocked carboxylic acid compounds for use in biobased epoxy-acid thermosets

245th National Meeting (2013)

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