Soluble Itaconic Acid–Ethylene Glycol Polyesters

Abstract

A method of obtaining soluble itaconic acid (IA)–ethylene glycol (EG) unsaturated polyesters was developed. The reaction between IA and EG was conducted under moderate vacuum (50—60 mmHg) at 120 °C and stopped by nearly 85% conversion to avoid crosslinking. No isomerization of itaconate to citraconate and/or mesaconate was observed. The residual double bond contained in the polyester resin showed to be highly reactive and promoted gelification after few days. Therefore copolymerization reactions of the resin with a variety of vinyl monomers proceed without radical initiator. The synthetic method was successfully applied to reactions of IA with other glycols.

Enzyme-Catalyzed Synthesis of Unsaturated Aliphatic Polyesters Based on Green Monomers from Renewable Resources

“…However, up until now, itaconate has not been well studied for polyester synthesis, neither by conventional catalysts nor by biocatalysts. Limited kinds of itaconate-based polyesters were synthesized using conventional chemical catalysts [8,9,10,43,44,45,46,47,48]. Only two papers referred to the enzymatic polymerizations of itaconate with other monomers: Barrett et al .…”

Enzymatic syntheses of unsaturated polyesters based on isosorbide and isomannide

“…Itaconic acid and its derivatives are currently used to produce photocurable polyesters . Early studies comprise thermal synthesis of unsaturated polyesters containing glycols and radical polymerization to produce oligomers with bromine contents used as plasticizer extenders to reduce flammability of polyvinyl chloride …”

Itaconic acid used as a versatile building block for the synthesis of renewable resource‐based resins and polyesters for future prospective: a review

“…At room temperature, in solution or solid form, poly(ethylene itaconate) easily undergoes crosslinking after 24 or 48 h even in the absence of any initiator. 58 Comparable results were also reported for the polymerization of itaconic anhydride with 1,2-epoxybutane in the presence of catalysts Mg(OEt) 2 , Al(OiPr) 3 , bis(nonafluorobutanesulfonyl) imide and Sc(OTf ) 3 . 59,60 Although, in this method, the polymerization was followed by isomerization of itaconate to cytraconate.…”

“…When the conversion of the monomer surpasses 85%, the lateral double bond becomes extremely reactive and hyper‐crosslinking is noted. At room temperature, in solution or solid form, poly(ethylene itaconate) easily undergoes crosslinking after 24 or 48 h even in the absence of any initiator …”