Toward new applications of terpenes in polymeric materials: Synthesis and characterization of myrcene‐modified unsaturated polyester resins

Abstract β‐Myrcene, a terpenic monomer, holds potential for developing sustainable polymer‐based materials with enhanced properties. This study examines the synthesis of a myrcene‐based monomer and its incorporation into unsaturated polyesters, focusing on polymerization, curing, and final properties. Unsaturated polyesters were synthesized with varying myrcene‐based monomer content (6, 12, and 24 mol%), phthalic anhydride, maleic anhydride, propylene glycol, ethylene glycol, and diethylene glycol. Polymerization achieved conversion values of 0.92–0.93, resulting in polyesters with molar masses between 1400 and 1700 g mol −1 and dispersity indices of 2.0 to 2.3. Nuclear magnetic resonance ( 1 H NMR) demonstrated short branch formation in myrcene‐modified polyesters and a high maleate‐to‐fumarate isomerization rate (92.66%–95.7%), affecting carbon–carbon double bonds per polyester mole (2.27 to 4.28) and final resin performance. Rheological analysis in a styrene solution (70/30 wt%) indicated shear‐thinning behavior, with viscosities ranging from 0.59 to 3.8 Pa·s, suggesting branching affects chain entanglement. Differential scanning calorimetry (DSC) revealed decreased curing enthalpy with increasing myrcene content, and it was inferred that myrcene's double bonds did not participate in curing. Glass transition temperatures of cured polyesters (70–107 °C) correlate with enthalpy trends. Thermal stability of myrcene‐modified polyesters is similar to the reference polyester, highlighting myrcene's potential as a sustainable monomer for customizable unsaturated polyesters.

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Publication Details

Journal
Journal of Applied Polymer Science
Published
2024-10-12
DOI
https://doi.org/10.1002/app.56381
Citations
1
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
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0.25
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article

Toward new applications of terpenes in polymeric materials: Synthesis and characterization of myrcene‐modified unsaturated polyester resins

Hortensia Maldonado‐Textle, Heriberto Rodríguez‐Tobías, José Luís Olivares-Romero, Judith Cabello-Romero et al.
1 citations
Journal of Applied Polymer Science
Synthetic Organic Chemistry Methods
0.25
article

Toward new applications of terpenes in polymeric materials: Synthesis and characterization of myrcene‐modified unsaturated polyester resins

Hortensia Maldonado‐Textle, Heriberto Rodríguez‐Tobías, José Luís Olivares-Romero, Judith Cabello-Romero, Ricardo Mendoza‐Carrizales, José Díaz‐Elizondo, Francisco Javier Enríquez‐Medrano, Myrna Salinas‐Hernández, Ramón Díaz de León
article en
1 citations

Abstract

Abstract β‐Myrcene, a terpenic monomer, holds potential for developing sustainable polymer‐based materials with enhanced properties. This study examines the synthesis of a myrcene‐based monomer and its incorporation into unsaturated polyesters, focusing on polymerization, curing, and final properties. Unsaturated polyesters were synthesized with varying myrcene‐based monomer content (6, 12, and 24 mol%), phthalic anhydride, maleic anhydride, propylene glycol, ethylene glycol, and diethylene glycol. Polymerization achieved conversion values of 0.92–0.93, resulting in polyesters with molar masses between 1400 and 1700 g mol −1 and dispersity indices of 2.0 to 2.3. Nuclear magnetic resonance ( 1 H NMR) demonstrated short branch formation in myrcene‐modified polyesters and a high maleate‐to‐fumarate isomerization rate (92.66%–95.7%), affecting carbon–carbon double bonds per polyester mole (2.27 to 4.28) and final resin performance. Rheological analysis in a styrene solution (70/30 wt%) indicated shear‐thinning behavior, with viscosities ranging from 0.59 to 3.8 Pa·s, suggesting branching affects chain entanglement. Differential scanning calorimetry (DSC) revealed decreased curing enthalpy with increasing myrcene content, and it was inferred that myrcene's double bonds did not participate in curing. Glass transition temperatures of cured polyesters (70–107 °C) correlate with enthalpy trends. Thermal stability of myrcene‐modified polyesters is similar to the reference polyester, highlighting myrcene's potential as a sustainable monomer for customizable unsaturated polyesters.

Journal of Applied Polymer ScienceVol. 142(3)
Instituto de Ecología (MX)
Industry, innovation and infrastructure
Openalex Percentile: Top 48%
Synthetic Organic Chemistry Methods
0.25
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