Articles producció científica> Química Analítica i Química Orgànica

Synthesis and characterization of new bio-based poly(acylhydrazone) vanillin vitrimers

  • Identification data

    Identifier: imarina:9246551
    Authors:
    Roig, AdriaPetrauskaite, AinaRamis, XavierDe la Flor, SilviaSerra, Angels
    Abstract:
    New acylhydrazone vitrimeric-type materials have been studied. These materials can be efficiently relaxed, without the addition of an external catalyst, through an exchange process that has been confirmed as imine metathesis, which differs from the previously reported transimination process in linear polymers. This is the first article that develops vitrimers with high T-g and fast relaxation based on poly(acylhydrazone)s. These materials have been prepared by condensing stoichiometric amounts of glycidyl vanillin and aliphatic dihydrazides of different chain lengths. The curing reaction takes advantage of the different reactivity of formyl and glycidyl groups and proceeds in two sequential steps: a first condensation of the formyl group of vanillin with dihydrazide monomers at low temperature followed by reaction of the remaining hydrazides with the epoxide, which requires temperatures above 150 degrees C. The complete disappearance of the initial reactive groups has been confirmed by FTIR spectroscopy. The thermomechanical characteristics have been evaluated by DMTA, obtaining T(g)s above 100 degrees C for the materials prepared, which present excellent vitrimeric features with very short relaxation times. Using model compounds, we were able to demonstrate that imine metathesis is responsible for the exchange process. The thermal stability of these materials has been rated by TGA. Poly(acylhydrazone) materials showed good recycling and self-healing abilities and could be hydrolyzed in an acidic medium.
  • Others:

    Author, as appears in the article.: Roig, Adria; Petrauskaite, Aina; Ramis, Xavier; De la Flor, Silvia; Serra, Angels
    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: Shape-memory Polymers Hydrogels Exchange Epoxy Dynamers
    Abstract: New acylhydrazone vitrimeric-type materials have been studied. These materials can be efficiently relaxed, without the addition of an external catalyst, through an exchange process that has been confirmed as imine metathesis, which differs from the previously reported transimination process in linear polymers. This is the first article that develops vitrimers with high T-g and fast relaxation based on poly(acylhydrazone)s. These materials have been prepared by condensing stoichiometric amounts of glycidyl vanillin and aliphatic dihydrazides of different chain lengths. The curing reaction takes advantage of the different reactivity of formyl and glycidyl groups and proceeds in two sequential steps: a first condensation of the formyl group of vanillin with dihydrazide monomers at low temperature followed by reaction of the remaining hydrazides with the epoxide, which requires temperatures above 150 degrees C. The complete disappearance of the initial reactive groups has been confirmed by FTIR spectroscopy. The thermomechanical characteristics have been evaluated by DMTA, obtaining T(g)s above 100 degrees C for the materials prepared, which present excellent vitrimeric features with very short relaxation times. Using model compounds, we were able to demonstrate that imine metathesis is responsible for the exchange process. The thermal stability of these materials has been rated by TGA. Poly(acylhydrazone) materials showed good recycling and self-healing abilities and could be hydrolyzed in an acidic medium.
    Thematic Areas: Química Polymers and plastics Polymer science Organic chemistry Engenharias ii Biomedical engineering Bioengineering Biochemistry
    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/submittedVersion
    Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2022/py/d1py01694f
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Polymer Chemistry. 13 (11): 1510-1519
    APA: Roig, Adria; Petrauskaite, Aina; Ramis, Xavier; De la Flor, Silvia; Serra, Angels (2022). Synthesis and characterization of new bio-based poly(acylhydrazone) vanillin vitrimers. Polymer Chemistry, 13(11), 1510-1519. DOI: 10.1039/d1py01694f
    Article's DOI: 10.1039/d1py01694f
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2022
    Publication Type: Journal Publications
  • Keywords:

    Biochemistry,Bioengineering,Biomedical Engineering,Organic Chemistry,Polymer Science,Polymers and Plastics
    Shape-memory
    Polymers
    Hydrogels
    Exchange
    Epoxy
    Dynamers
    Química
    Polymers and plastics
    Polymer science
    Organic chemistry
    Engenharias ii
    Biomedical engineering
    Bioengineering
    Biochemistry
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