From plant oils to plant foils: Straightforward functionalization and crosslinking of natural plant oils with triazolinediones

Türünç, Oğuz; Billiet, Stijn; Bruycker, Kevin De; Ouardad, Samira; Winne, Johan M.; Prez, Filip Du

doi:10.1016/j.eurpolymj.2014.12.013

Cited by 46 publications

(27 citation statements)

References 36 publications

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“…The group reported ultrafast reversible TAD click reactions of polyacrylates with indole groups to create dynamic polymer networks . The same group also applied a difunctional TAD for the cross‐linking of various unsaturated plant oils to produce films and particles …”

Section: Introductionmentioning

confidence: 99%

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Hanay

Ritzen

Brougham

et al. 2017

Macromolecular Bioscience

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Highly efficient functionalization and cross-linking of polypeptides is achieved via tyrosine-triazolinedione (TAD) conjugation chemistry. The feasibility of the reaction is demonstrated by the reaction of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) with tyrosine containing block copolymer poly(ethylene glycol)-Tyr as well as a statistical copolymer of tyrosine and lysine (poly(Lys -st-Tyr )) prepared form N-carboxyanhydride polymerization. Selective reaction of PTAD with the tyrosine units is obtained and verified by size exclusion chromatography and NMR spectroscopy. Moreover, two monofunctional and two difunctional TAD molecules are synthesized. It is found that their stability in the aqueous reaction media significantly varied. Under optimized reaction conditions selective functionalization and cross-linking, yielding polypeptide hydrogels, can be achieved. TAD-mediated conjugation can offer an interesting addition in the toolbox of selective (click-like) polypeptide conjugation methodologies as it does not require functional non-natural amino acids.

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Section: Introductionmentioning

confidence: 99%

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Hanay

Ritzen

Brougham

et al. 2017

Macromolecular Bioscience

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“…TAD, being one of the strongest ene-and dienophiles in organic chemistry [37][38][39][40], can undergo efficient and ultrafast irreversible 'click' reactions with a variety of olefinic compounds in either a Diels-Alder or an Alder-ene reaction (Scheme 1). TAD compounds have been used for various polymer modification [41,42] and a range of applications has recently been reported [43][44][45][46].…”

Section: Introductionmentioning

confidence: 99%

Biodegradable polymer networks via triazolinedione-crosslinking of oleyl-functionalized poly(ε-caprolactone)

Baśko

Bednarek

Vlaminck

et al. 2017

European Polymer Journal

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“…Recently, numerous polymer systems making use of a highly efficient click reaction, namely, the coupling of 1,2,4‐triazoline‐3,5‐dione (TAD) with double bonds according to DA or Alder–ene (AE) pathways, have been reported . In contrast to furan/maleimide DA reaction, this coupling reaction proceeds extremely fast at room temperature without the addition of any catalyst, leading to the formation of irreversible adducts in most cases . In addition, Baran et al reported a thermally reversible protection strategy of indole moieties by TAD via AE reaction at 0 °C .…”

Section: Introductionmentioning

confidence: 99%

Reversible TAD Chemistry as a Convenient Tool for the Design of (Re)processable PCL‐Based Shape‐Memory Materials

Defize

Riva

Thomassin

et al. 2016

Macromol. Rapid Commun.

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A chemically cross-linked but remarkably (re)processable shape-memory polymer (SMP) is designed by cross-linking poly(ε-caprolactone) (PCL) stars via the efficient triazolinedione click chemistry, based on the very fast and reversible Alder-ene reaction of 1,2,4-triazoline-3,5-dione (TAD) with indole compounds. Typically, a six-arm star-shaped PCL functionalized by indole moieties at the chain ends is melt-blended with a bisfunctional TAD, directly resulting in a cross-linked PCL-based SMP without the need of post-curing treatment. As demonstrated by the stress relaxation measurement, the labile character of the TAD-indole adducts under stress allows for the solid-state plasticity reprocessing of the permanent shape at will by compression molding of the raw cross-linked material, while keeping excellent shape-memory properties.

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From plant oils to plant foils: Straightforward functionalization and crosslinking of natural plant oils with triazolinediones

Cited by 46 publications

References 36 publications

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Biodegradable polymer networks via triazolinedione-crosslinking of oleyl-functionalized poly(ε-caprolactone)

Reversible TAD Chemistry as a Convenient Tool for the Design of (Re)processable PCL‐Based Shape‐Memory Materials

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