Glycidyl ester of versatic acid

Nondrying alkyd resins cross-linked with melamine resins at elevated temperature are used for industrial coatings. Resins containing synthetic fatty acids and resins based on glycidyl esters of Versatic Acid (Cardura E 10, Shell) are used in combination with low-viscosity melamine resins such as hexamethoxymethylmelamine. p-Toluenesulfonic acid and its amine salts are used as catalysts. On account of their high storage life, hydrophobic oxime esters of sulfonic acids are also employed. 

Synthesis from sucrose ester/half-ester derivatives, monoepoxide and diisocyanate. Sucrose "penta"-soyate (the methanol insoluble fraction of the soap-free product) was reacted at 100°C for 4 hours with a mixture in xylene of 1 mole equivalent cyclic anhydride e.g., phthalic or tetrahydrophthalic anhydride and monoepoxide e.g., styrene oxide or Cardura E (the glycidyl ester of versatic acid), branched C9-Cfatty acids, in the presence of N-benzyl dimethylamine as catalyst. A faster rate was achieved with the phthalic system. The course of reaction between half ester carboxyl groups and epoxide groups was followed by acid value. About 90% reaction was achieved in all cases and to the product was added 1.0 mole toluene diisocyanate (the meucimum amount without gelation) and dibutyl tin dilaurate as catalyst. 

Another interesting material often used in polyester resins is the glycidyl ester of versatic acid (Figure 2.14), a synthetic saturated monocarboxylic acid of highly branched Cj isomers. The highly branched alkyl group provides excellent wetting, exterior dura-biiity, hydrophobicity, flexibility and impact resistance, and acid etch resistance, and low viscosity. 

Cadura E Ester [Shell], TM for glycidyl ester of Versatic 911 Acid. 

---