Chemically crosslinked yet reprocessable epoxidized natural rubber via thermo-activated disulfide rearrangements

Imbernon, Lucie; Oikonomou, Evdokia K.; Norvez, Sophie; Leibler, Ludwik

doi:10.1039/c5py00459d

Cited by 268 publications

(227 citation statements)

References 36 publications

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“…As the temperature is further increased to 100 °C, almost 84% release of the internal stress within 60 min can be obtained. The relaxation time τ was determined at 37% (1/e) of the initial relaxation modulus, which was based on the the Maxwell model for viscoelastic polymers (eq ):

σ_{true(t true)} = σ_{0} e^{- t / τ}

…”

Section: Resultsmentioning

confidence: 99%

Dynamic cross-links to facilitate recyclable polybutadiene elastomer with excellent toughness and stretchability

Wang

Zhang

Cheng

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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A facile cross-linking strategy of using small molecules as physcial crosslinkers to facilitate recyclable polybutadiene (PB) elastomer with excellent toughness and stretchability is demonstrated. Carboxylic acid groups were incorporated along the PB backbone via thiol-ene reaction, and then the polymer can be cross-linked by ionic hydrogen bonds between the carboxylic acid groups from PB and the amine groups of the cross-linkers. The ionic hydrogen bonds can dynamiclly break and reconstruct upon deformation, thus endowing the resultant polymer with not only high toughness and stretchability (1800%), but also good selfrecovery and enhanced damping properties. Remarkably, the dynamically cross-linked PB elastomer can be thermally recycled owing to the thermal reversibility of the ionic hydrogen bonds and the mechanical properties can be largely recovered after reprocessing.

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σ_{true(t true)} = σ_{0} e^{- t / τ}

…”

Section: Resultsmentioning

confidence: 99%

Dynamic cross-links to facilitate recyclable polybutadiene elastomer with excellent toughness and stretchability

Wang

Zhang

Cheng

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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“…DTDB is an organic sulfur compound used in diverse technical applications, such as in the production of chemically crosslinked epoxidized natural rubber [11] and as an alternative monolayer for protein chips [12, 13]. Furthermore, DTDB is considered as an alternative promising substrate for PTE synthesis.…”

Section: Introductionmentioning

confidence: 99%

Genome and Proteome Analysis of Rhodococcus erythropolis MI2: Elucidation of the 4,4´-Dithiodibutyric Acid Catabolism

Khairy¹,

Meinert²,

Wübbeler³

et al. 2016

PLoS ONE

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Rhodococcus erythropolis MI2 has the extraordinary ability to utilize the xenobiotic 4,4´-dithiodibutyric acid (DTDB). Cleavage of DTDB by the disulfide-reductase Nox, which is the only verified enzyme involved in DTDB-degradation, raised 4-mercaptobutyric acid (4MB). 4MB could act as building block of a novel polythioester with unknown properties. To completely unravel the catabolism of DTDB, the genome of R. erythropolis MI2 was sequenced, and subsequently the proteome was analyzed. The draft genome sequence consists of approximately 7.2 Mbp with an overall G+C content of 62.25% and 6,859 predicted protein-encoding genes. The genome of strain MI2 is composed of three replicons: one chromosome and two megaplasmids with sizes of 6.45, 0.4 and 0.35 Mbp, respectively. When cells of strain MI2 were cultivated with DTDB as sole carbon source and compared to cells grown with succinate, several interesting proteins with significantly higher expression levels were identified using 2D-PAGE and MALDI-TOF mass spectrometry. A putative luciferase-like monooxygenase-class F420-dependent oxidoreductase (RERY_05640), which is encoded by one of the 126 monooxygenase-encoding genes of the MI2-genome, showed a 3-fold increased expression level. This monooxygenase could oxidize the intermediate 4MB into 4-oxo-4-sulfanylbutyric acid. Next, a desulfurization step, which forms succinic acid and volatile hydrogen sulfide, is proposed. One gene coding for a putative desulfhydrase (RERY_06500) was identified in the genome of strain MI2. However, the gene product was not recognized in the proteome analyses. But, a significant expression level with a ratio of up to 7.3 was determined for a putative sulfide:quinone oxidoreductase (RERY_02710), which could also be involved in the abstraction of the sulfur group. As response to the toxicity of the intermediates, several stress response proteins were strongly expressed, including a superoxide dismutase (RERY_05600) and an osmotically induced protein (RERY_02670). Accordingly, novel insights in the catabolic pathway of DTDB were gained.

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“…Currently, as recently reviewed by our group9, only a limited number of associative exchange chemistries101112131415161718192021222324 have been explored in the context of vitrimers, and one of the main challenges is the precise control of the exchange kinetics. Although Leibler and co-workers demonstrated that epoxy-based transesterification vitrimers can be controlled by changing catalysts8, the exchange reaction remains slow and high catalyst loadings and temperatures are required to enable processing in a reasonable timeframe678.…”

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confidence: 99%

Chemical control of the viscoelastic properties of vinylogous urethane vitrimers

et al. 2017

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Vinylogous urethane based vitrimers are polymer networks that have the intrinsic property to undergo network rearrangements, stress relaxation and viscoelastic flow, mediated by rapid addition/elimination reactions of free chain end amines. Here we show that the covalent exchange kinetics significantly can be influenced by combination with various simple additives. As anticipated, the exchange reactions on network level can be further accelerated using either Brønsted or Lewis acid additives. Remarkably, however, a strong inhibitory effect is observed when a base is added to the polymer matrix. These effects have been mechanistically rationalized, guided by low-molecular weight kinetic model experiments. Thus, vitrimer elastomer materials can be rationally designed to display a wide range of viscoelastic properties.

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Chemically crosslinked yet reprocessable epoxidized natural rubber via thermo-activated disulfide rearrangements

Abstract: Disulfide crosslinks introduced into an ENR matrix enable the thermo-activated reprocessing of the chemically crosslinked rubber, studied in terms of stress relaxation and adhesion experiments.

Cited by 268 publications

References 36 publications

Dynamic cross-links to facilitate recyclable polybutadiene elastomer with excellent toughness and stretchability

Dynamic cross-links to facilitate recyclable polybutadiene elastomer with excellent toughness and stretchability

Genome and Proteome Analysis of Rhodococcus erythropolis MI2: Elucidation of the 4,4´-Dithiodibutyric Acid Catabolism

Chemical control of the viscoelastic properties of vinylogous urethane vitrimers

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