Abstract
The polycondensation of long-chain α,ω-diesters with long-chain α,ω-diols, prepared by means of catalytic conversion of plant oils, affords linear aliphatic polyesters. They contain both long crystallizable polyethylene-like hydrocarbon segments and ester moieties in the backbone. In a convenient catalytic one-step process a high-purity polycondensation grade dimethyl-1,19-nonadecanedioate monomer is obtained directly from the technical grade methyl ester of high oleic sunflower oil. Likewise, dimethyl-1,23-tricosanedioate is derived from methyl erucate. The successful scale-up renders both intermediates available on a 100 g scale. Injection molded parts of polyester-19.19 and -23.23 with a number average molecular mass of Mn = 3 × 104 g mol−1 possess an elongation at break of >600% and a Young's modulus of 400 MPa. Electrospinning produces non-woven meshes. The polyesters prepared even enable film extrusion and represent new blend components for a variety of thermoplastics including polyethylene.
Highlights
Dicarboxylic acids derived from plant oils are attractive intermediates for the synthesis of polymer materials.[1]
These findings show that useful and attractive materials properties can be achieved for aliphatic polyesters generated by polycondensation of long-chain aliphatic diacids with longchain diols
This is relevant, amongst others, as melting and crystallization temperatures of these new materials are advantageously high in comparison with existing shorter chain aliphatic polyesters
Summary
Dicarboxylic acids derived from plant oils are attractive intermediates for the synthesis of polymer materials.[1]. Long-chain aliphatic polyesters from plant oils for injection molding, film extrusion and electrospinning† Dicarboxylic acids derived from plant oils are attractive intermediates for the synthesis of polymer materials.[1] Similar to polyethylene, the incorporation of long methylene sequences enables polymer crystallization and renders polyesters hydrophobic.
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