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Disulfide vitrimeric materials based on cystamine and diepoxy eugenol as bio-based monomers

  • Identification data

    Identifier: imarina:9325538
    Authors:
    Roig, AdriaAgizza, MarcoSerra, AngelsDe la Flor, Silvia
    Abstract:
    This study reports the synthesis and characterization of bio-based disulfide vitrimers obtained from diepoxy eugenol and cystamine through an epoxy-amine polycondensation process. TREN was added to the formulation in varying proportions to increase the crosslinking density. Although TREN reduced the number of disulfide groups in the vitrimers, it resulted in a maximum relaxation rate at a proportion of 25%. The vitrimers were characterized using FTIR, TGA, and thermomechanical analysis, and their Tg values, determined by DSC, ranged from 75 to 103 °C with increasing TREN proportion. The vitrimers rapidly relax with a relaxation time (τ) of 8.5 min at 170 °C. The addition of TREN decreased the relaxation times from 2.8 to 1.03 min by catalyzing the disulfide metathesis and achieving a balance between the proportion of disulfide bonds and the content of nucleophilic tertiary amines. Creep tests were performed at a wide range of temperatures to investigate the viscosity of the material below and above the Tgs. The topology freezing temperatures were calculated from the creep tests, and Tv values below Tg in all cases confirmed the catalytic effect of tertiary amines on the disulfide exchange reaction.
  • Others:

    Author, as appears in the article.: Roig, Adria; Agizza, Marco; Serra, Angels; De la Flor, Silvia
    Department: Enginyeria Mecànica Química Analítica i Química Orgànica
    URV's Author/s: De la Flor Lopez, Silvia / Roig De Arespacochaga, Anna / Serra Albet, Maria Angels
    Keywords: Vitrimers Internal catalysis Eugenol Disulfide Cystamine Bio-based
    Abstract: This study reports the synthesis and characterization of bio-based disulfide vitrimers obtained from diepoxy eugenol and cystamine through an epoxy-amine polycondensation process. TREN was added to the formulation in varying proportions to increase the crosslinking density. Although TREN reduced the number of disulfide groups in the vitrimers, it resulted in a maximum relaxation rate at a proportion of 25%. The vitrimers were characterized using FTIR, TGA, and thermomechanical analysis, and their Tg values, determined by DSC, ranged from 75 to 103 °C with increasing TREN proportion. The vitrimers rapidly relax with a relaxation time (τ) of 8.5 min at 170 °C. The addition of TREN decreased the relaxation times from 2.8 to 1.03 min by catalyzing the disulfide metathesis and achieving a balance between the proportion of disulfide bonds and the content of nucleophilic tertiary amines. Creep tests were performed at a wide range of temperatures to investigate the viscosity of the material below and above the Tgs. The topology freezing temperatures were calculated from the creep tests, and Tv values below Tg in all cases confirmed the catalytic effect of tertiary amines on the disulfide exchange reaction.
    Thematic Areas: Química Polymers and plastics Polymer science Physics and astronomy (miscellaneous) Physics and astronomy (all) Organic chemistry Odontología Materials chemistry Materiais Interdisciplinar General physics and astronomy Farmacia Engenharias iv Engenharias iii Engenharias ii Engenharias i Ciências ambientais Ciência de alimentos Ciência da computação Biotecnología Astronomia / física Arquitetura, urbanismo e design
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: angels.serra@urv.cat silvia.delaflor@urv.cat
    Author identifier: 0000-0003-1387-0358 0000-0002-6851-1371
    Record's date: 2024-11-02
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://www.sciencedirect.com/science/article/pii/S0014305723003683
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: European Polymer Journal. 194 112185-
    APA: Roig, Adria; Agizza, Marco; Serra, Angels; De la Flor, Silvia (2023). Disulfide vitrimeric materials based on cystamine and diepoxy eugenol as bio-based monomers. European Polymer Journal, 194(), 112185-. DOI: 10.1016/j.eurpolymj.2023.112185
    Article's DOI: 10.1016/j.eurpolymj.2023.112185
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2023
    Publication Type: Journal Publications
  • Keywords:

    Materials Chemistry,Organic Chemistry,Physics and Astronomy (Miscellaneous),Polymer Science,Polymers and Plastics
    Vitrimers
    Internal catalysis
    Eugenol
    Disulfide
    Cystamine
    Bio-based
    Química
    Polymers and plastics
    Polymer science
    Physics and astronomy (miscellaneous)
    Physics and astronomy (all)
    Organic chemistry
    Odontología
    Materials chemistry
    Materiais
    Interdisciplinar
    General physics and astronomy
    Farmacia
    Engenharias iv
    Engenharias iii
    Engenharias ii
    Engenharias i
    Ciências ambientais
    Ciência de alimentos
    Ciência da computação
    Biotecnología
    Astronomia / física
    Arquitetura, urbanismo e design
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