The use of ionic liquids as an organocatalyst for controlled ring-opening polymerization of ϵ-caprolactone

Kaoukabi, Asmae; Guillen, Frédéric; Qayouh, Hicham; Bouyahya, Asmaa; Balieu, Sébastien; Belachemi, Larbi; Gouhier, Géraldine; Lahcini, Mohammed

doi:10.1016/j.indcrop.2015.02.002

Cited by 16 publications

(7 citation statements)

References 34 publications

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“…Among synthetic polymers, aliphatic polyesters have been the subject of a growing number of investigations. In light of the benefits that they offer, like functionality and biocompatibility, various applications or product segments are currently exhibiting high growth rates [ 14 , 15 , 16 , 17 ]. Previously, hemicellulosic-based copolymers had been developed by grafting with polyesters, including poly(ε-caprolactone) (PCL) [ 11 ], poly( l -lactide) (PLA) [ 18 , 19 ], and poly(propylene carbonate) (PPC) [ 20 ], which showed good solubility in organic solvents, a film-forming property, and thermoplasticity.…”

Section: Introductionmentioning

confidence: 99%

Organic Catalysis for Ring-Opening Graft Polymerization of p-Dioxanone with Xylan in Ionic liquid

et al. 2017

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Abstract:Recently, organic catalysis has become a powerful alternative to the use of more traditional metal-based catalysts. In this study, 4-dimethylaminopyridine (DMAP), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were applied to mediate the ring-opening graft polymerization (ROGP) of p-dioxanone (PDO) with xylan-based hemicelluloses in ionic liquid 1-butyl-3-methylimidazolium chloride ([Bmim]Cl). Excellent control of the molar ratio of the catalyst to anhydroxylose units (AXU) in xylan was found for a good tuning of the weight percent gain (WPG) of xylan-graft-poly(p-dioxanone) (xylan-g-PPDO) copolymers. As a result, the maximum WPG of xylan-g-PPDO copolymers was 431.07% (DMAP/AXU of 2/1), 316.72% (DBU/AXU of 0.2/1), and 323.15% (TBD/AXU of 0.2/1), respectively. The structure of xylan-g-PPDO copolymers was characterized with FT-IR and NMR. The thermal properties of copolymers were investigated using thermogravimetric analysis (TGA/DTG) and differential scanning calorimetry (DSC), and a significant difference was observed regarding the transition temperature (T g ), melting temperature (T m ), and crystallization temperature (T c ).

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Section: Introductionmentioning

confidence: 99%

Organic Catalysis for Ring-Opening Graft Polymerization of p-Dioxanone with Xylan in Ionic liquid

et al. 2017

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“…Since they are nonflammable, non-volatile and recyclable, they are greener alternatives to conventional organic solvents. Furthermore, they may be used as effective and reusable catalysts in some polymerization reactions [9][10][11][12][13] and as initiators of free-radical [14,15] or cationic [16,17] polymerization processes. Thus, ILs have attracted widespread interest in polymer chemistry, due to their versatile properties [18,19].…”

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confidence: 99%

Effect of ionic liquids on kinetic parameters of dicyanate ester polycyclotrimerization and on thermal and viscoelastic properties of resulting cyanate ester resins

Fainleib¹,

Grigoryeva²,

Vashchuk³

et al. 2019

Express Polym. Lett.

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Cyanate ester resins (CERs) represent a family of thermosetting polymers possessing attractive intrinsic features, such as excellent dimensional stability, high glass transition temperature (T g > 250°С), low dielectric constants (2.5-3.2), flame-retardancy, and high adhesion to conductor metals and composites. Therefore, they are promising materials for aerospace and microelectronic applications, especially as polymer matrices for structural composites, adhesives, potting resins, and coatings that work under severe conditions (high temperature, humidity, corrosive media, etc) [1][2][3][4][5][6]. Dicyanate ester monomers undergo thermal polycyclotrimerization to generate high T g polycyanurate networks (PCNs), i.e. cyanate ester resins (CERs), without releasing volatile products. Figure 1 describes the reaction scheme of polycyclotrimerization of one of the widely used monomers, i.e. dicyanate ester of bisphenol E (DCBE). Dicyanate ester homopolymerization occurs at high temperature in the presence or the absence of a specific catalyst. The rate of non-catalyzed polycyclo -Abstract. A strong catalytic effect of 1.0 wt% ionic liquids (ILs) on kinetic parameters of dicyanate ester of bisphenol E (DCBE) polycyclotrimerization was evidenced, and structure-property relationships of resulting densely cross-linked cyanate ester resins (CERs) were investigated. Three different ILs with contrasted reactivity were employed as a catalysts: an aprotic IL, i.e. 1-octyl-3-methyl imidazolium tetrafluoroborate ([OMIm][BF 4 ]), a protic IL, i.e. 2-(hydroxyethylamino) imidazolinium chloride ([HEAIm][Cl]), and a protic polymeric IL, i.e. poly(hexamethylene guanidine) toluene sulfonate ([PHMG][TS]). Both [HEAIm][Cl] and [PHMG][TS] were reactive towards DCBE monomer, whereas [OMIm] [BF 4 ] was chemically inert, as confirmed by Fourier Transform Infrared (FTIR) spectroscopy. Noticeably, the conversion (α c ) of cyanate groups in the presence of ILs dramatically increased, and a significant dependence of α c values on IL chemical structure was found. The corresponding mechanisms of DCBE polycyclotrimerization in the presence of different ILs were proposed. All the CER/IL networks exhibited a high thermal stability inherent to neat CER, as shown by TGA, whereas unexpected significant changes of the viscoelastic characteristics for CER/IL networks compared to pure CER analogue were observed using DMTA.

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“…The same behavior was observed by Ensafi et al., in their work about the determination of morphine . The poly‐pPDs‐IL/CPE shows a low resistance compared to the other electrodes (1751 Ω), the electron transfer rate was then improved which can be attributed to the ionic liquid that act as polymerization catalyst . The results of R ct reflect the role of the composite to accelerate the electron transfer at the electrode surface due to synergetic effect between the polymer and ionic liquid.…”

Section: Resultsmentioning

confidence: 99%

Conducting Polymer/Ionic Liquid Composite Modified Carbon Paste Electrode for the Determination of Carbaryl in Real Samples

et al. 2018

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A new method has been described for carbaryl determination using a simple electrochemical sensor. The unique properties of poly‐pPhenylenediamine and ionic liquid were exploited to fabricate carbon paste electrode modified with composite based on conducting polymer/ionic liquid. Electrode surface characterization was performed by electrochemical methods (cyclic voltammetry and electrochemical impedance spectroscopy) and by scanning electron microscopy. Differential pulse voltammetry was employed for the detection of carbaryl in acetate buffer solution. Different parameters affecting the carbaryl response were optimized such as ionic liquid amounts, cycle number of polymerization and monomer concentration, pH, and accumulation time. Under the optimum experimental conditions, a linear response was obtained between 0.5 and 200 μmol/L, with detection limit of 0.09 μmol/L. The developed sensor offered satisfactory results for carbaryl detection in spring water and fruit samples.

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The use of ionic liquids as an organocatalyst for controlled ring-opening polymerization of ϵ-caprolactone

Cited by 16 publications

References 34 publications

Organic Catalysis for Ring-Opening Graft Polymerization of p-Dioxanone with Xylan in Ionic liquid

Organic Catalysis for Ring-Opening Graft Polymerization of p-Dioxanone with Xylan in Ionic liquid

Effect of ionic liquids on kinetic parameters of dicyanate ester polycyclotrimerization and on thermal and viscoelastic properties of resulting cyanate ester resins

Conducting Polymer/Ionic Liquid Composite Modified Carbon Paste Electrode for the Determination of Carbaryl in Real Samples

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